Online Shopping Picks: The Best Men’s Chukka Boots for Fall

Editor’s note: For a full set of menswear shopping picks, click that link.

If you’ve followed along with The Style Guide since the very beginning (way back in 2013, folks), you might recall your author extolling the virtues of certain style essentials. Although there are basics like a classic blue Oxford and slim dark denim  for your top half, those essentials can be a bit more difficult to pin down in terms of footwear. Or are they? One of those key pieces is absolutely the chukka boot. Versatile, durable, wearable no matter the weather. That being said, there’s no better time to get your footwear wardrobe refreshed (or started, or added onto) than during the fall. It’s perhaps the best time of the year for menswear, what with layering and rugged textures galore — and even if you live in a temperate climate, maybe you’ve got a special place in your heart for today’s topic: The best men’s chukka boots for fall. The time just feels right to dive into a bevy of boots that can exude style both rugged and refined, dressy and casual. That’s darn near the definition of a style essential, and it’s as good of a place to start as any in today’s latest menswear shopping picks entry. Of course, there are all kinds of other boot styles out there for fall and winter (wingtip boots, anyone?), but rest assured we’ll get to those in good time. Want to see how to style chukka boots? Head to Instagram or search this site’s archives (or heck, head on over to Twitter, too).

#1. Thursday Boots Whiskey Scout Boot — $149

A rich pair of brown leather chukkas practically made for fall.

A rich pair of brown leather chukkas practically made for fall.

Having tried everything from the much-loved Roughout Captain Boot to the dependable Suede Scout Chukka, this #menswear writer can definitely vouch for the value inherent in Thursday Boots’ footwear assortment. Checking out the Brown Scout Chukka during a spring trip to Washington, D.C. sealed the deal for me as far as the brand’s chukkas go, and it’s very safe to assume that the rich Whiskey Scout Boot will perform much the same. The color is, quite simply, handsome and very wearable with everything from crisp olive chinos and a cream cable sweater to a worsted wool suit. For the price, that’s applause-worthy.

#2. JackThreads Mac Desert Chukka — $80

A new footwear introduction from a brand that can do just about everything.

A new footwear introduction from a brand that can do just about everything.

It might not surprise you to read that JackThreads made an Online Shopping Picks entry on this site. However, what might come as a shock is that the much-loved E-commerce retailer now has a line of footwear to back up the rest of its affordably priced, stylish menswear line.  Let’s start with the important stuff. First off, that combination of looks and price — can’t beat it. $80 for a chukka that bears the JackThreads name is A-plus, truly. The lower profile, Taupe colorway and crepe sole make them the ideal weekend chukka — pair them with a broken-in pair of blue denim and a crewneck sweater for a put-together casual look, or mash them up with slim wool trousers and a navy cardigan to head back to the office. Oh, and pick up a second pair while you’re at it — did we mention the excellent price?
Buck Mason - Timeless Design. Made in America.

#3. Johnston & Murphy Copeland Chukka — $155

Equal parts casual and sharp.

Equal parts casual and sharp.

If the Thursday Boots chukka seen at the top of the page is a dressy chukka boot, and the JackThreads chukka boot seen here above is a casual chukka boot, the Johnston & Murphy Copeland Chukka is something of a hybrid. Featuring  a deep red-brown oiled nubuck that should break in beautifully, the contrast stitching and crepe sole give it a casual feel. But make no mistake, this is a still a dependable leather chukka boot you should pair up with navy suit trousers and a grey cardigan, or a broken-in pocket tee and dark denim for weekend errands.
Buck Mason - Timeless Design. Made in America.

#4. SWIMS Barry Chukka in Taupe/Biscuit — $230

Casual, reliable and waterproof, all at the same time.

Casual, reliable and waterproof, all at the same time.

Chukka boots that offer a little bit of everything are nice to have on-hand — especially if your fall adventures take you everywhere from a football game to park hikes to pumpkin patches (yes, we’re going there already). In particular, these SWIMS chukka boots are fully waterproof, and combine the styling potential of a casual crepe sole with the functionality needed for tricky fall weather. The silhouette feels more like a sneaker than a classic chukka boot, and that’s not a bad thing — this pair would work especially well with burgundy corduroys and a long-sleeve merino tee for aforementioned weekend adventures.

Related: The Best Suede Chukka Boots to Buy Right Now

#5. Red Wing Heritage Weekender Chukka — $230

A unique chukka boot that works for both spring and summer style scenarios.

A unique chukka boot that works for both spring and summer style scenarios.

If you perused the pages of this site back in July, you’re familiar with the Red Wing Heritage Weekender Chukka. It’s a lighter-weight chukka boot that works equally well in the spring and summer as it does during the fall and winter — that makes it worth the price alone. It’s a new addition to the Red Wing Heritage line that plays off the brand’s rugged heritage while offering up a bit more flexibility and comfort than a thick-soled pair of winter boots. We’ll get to that point in the season eventually, but for now, know that you just might have a chukka boot fit for adventures seven days a week — and then some. They’re the ideal complement to classic navy chinos, and they’ll put in plenty of hours beneath trusty dark denim and a slim fall flannel shirt.

Did the above list of the best men’s chukka boots get you thinking  a bit? A trusty pair of chukka boots can seriously become a multi-day workhorse in your footwear arsenal, easily wearable with business-casual or weekend-casual outfits. Embracing the changing seasons can be a whole lot easier if you have the right gear to wear, too. That certainly starts with a rugged, dependable pair of chukka boots – after all, there really aren’t too many fall-centric outfits that don’t start with a great pair of boots (or maybe that’s just your author’s opinion). And with such great variety on the market — from a fresh style done by a heritage brand to an entirely new E-commerce offering from JackThreads — there are plenty of picks worth exploring. Want to share your own? Leave a note in the Comments section below!

Until our next menswear shopping picks post — coming next week — stay tuned for the Friday Read, and stay stylish.

-Beau

Standout style: Rocking out at Panorama 2016

Editor’s note: Start here for personal style #menswear coverage.

The heat didn't stop me from rocking out in style. Linen-blend shirt by Old Navy. Silm Light Mercer Denim by Mott & Bow. Natural Diplomat Boots by Thursday Boots. Millbrook Sunglasses by Steven Alan Optical. Mod Watch from the Timex x Todd Snyder collab.

The heat didn’t stop me from rocking out in style. Linen-blend shirt by Old Navy. Silm Light Mercer Denim by Mott & Bow. Natural Diplomat Boots by Thursday Boots. Millbrook Sunglasses by Steven Alan Optical. Mod Watch from the Timex x Todd Snyder collab.

Here at The Style Guide, I’m pretty thankful to get to write about what I love every week. But it’s even better when I get to combine my passions into one post, as I did this weekend when I headed to the first-ever Panorama festival in NYC rocking some great men’s style gear and rocking out to excellent tunes along the way. Panorama was a unique merger of music, art and technology, curated by the same team behind Coachella – and Saturday’s lineup, featuring luminaries like Kendrick Lamar, Sufjan Stevens and The National, was stellar. The festival blended the buzzing atmosphere with some premium food and beverage curated in part by the great folks at Eater.com, too.And of course, the day presented the perfect opportunity for me to combine those aforementioned passions into one heck of an afternoon (although if you follow me on Twitter or Instagram, you’re aware of that!). Now, attending an outdoor festival in the heat of summer might seem like the opportune time to ditch decorum and dress to stay cool, but yours truly thinks just the opposite — bear with me.

Of note, stepping out on Saturday put me right smack-dab in the middle of some very hot weather — it was sunny, beautiful and in the 90s here in the Big Apple.  Even still, I was glad to be there as Panorama took over Randall’s Island, the site of this summer’s Governors Ball festival, (a similarly spectacular weekend). It was exciting to know that a quick subway trip brought me mere feet from (among others), The National, supremely talented purveyors of emotionally substantive music … but more on that in a second. Just know that for now, if you get the chance to see them, it’s a must. And if you manage to get as close as I somehow did, it’ll be even more astounding (just check out this video here, for one!).

Join Frank & Oak Elevate - Enjoy FREE Shipping, Cashback + more at Frank + Oak! Try it now for 90 days, risk free!To tackle the festival in style, I reached for a new pair of Thursday Boots — they’re a big Style Guide favorite for the way they blend price, quality and styling potential, and I tested out the rugged-refined Natural Diplomat Boot this weekend. It’s made from durable Horween leather that provided just the right amount of toughness, edge and style, plus excellent grip and plenty of durability for playing a little air guitar during a high-voltage afternoon set from British rockers Foals. Of course, they had to be able to fight for a spot in the crowd during a visually stunning show by Sufjan Stevens — and before that, I did plenty of rocking out to The National, one of my all-time favorite bands and the group behind one of my all-time favorite albums (that would be Boxer …. or perhaps it’s Trouble Will Find Me …. or maybe Alligator…). The band’s incredible, emotional show came after a blisteringly hot day out and about, and it’s a good thing I had apparel that stood up to the test. Challenges with the heat started early, even during a high-energy, engaging set from British duo Oh Wonder to kick off the day (note that if you dig what you hear from them, they’re working on a new album!).

Ready for a full day of rocking out. Linen-Blend Shirt by Old Navy. Slim Light Mercer Denim by Mott & Bow. Natural Diplomat Boots by Thursday Boots. Troubadour Socks by Richer Poorer. Hudson Belt by Arcade Belts. Adventure Log by Word Notebooks. Wristband by Panorama NYC.

Ready for a full day of rocking out. Linen-Blend Shirt by Old Navy. Slim Light Mercer Denim by Mott & Bow. Natural Diplomat Boots by Thursday Boots. Troubadour Socks by Richer Poorer. Hudson Belt by Arcade Belts. Adventure Log by Word Notebooks. Wristband by Panorama NYC.

Attending a great music festival often feels like multiple shows within one large, high-energy show — it’s fitting then, that my style blended multiple elements. To fight the heat (and yes, I’m aware I chose boots and denim), a linen-blend short-sleeve shirt courtesy of Old Navy worked quite well. Although the Navy color is now sold out, the white Flax Linen option on the site would be a reliable stand-in at your next music festival, with a much-needed linen blend and utilitarian chest pockets. It really was crucial to have versatile style, as the day shifted from a eclectic, mellow vibes of Oh Wonder  to a high-energy set put on Daughter. The quickly changing scenery called for durable accessories, too — no busted watches or sunglasses left behind here. Plus, my Tread for Men Traveler Sunscreen was a big help in protecting me from the sun.
Buck Mason - Timeless Design. Made in America.

Chief among the rest of those accessories was a new personal favorite, the outstanding Timex x Todd Snyder Mod Watch. It reliably updates a vintage style for the modern man. I accentuated that crisp watch with a fun-to-wear pair of Millbrook sunglasses via Steven Alan Optical, which clock in at an agreeable price on top of great looks ($165). Certainly, every cent helps when cooling down with some nice refreshments and powering through a day of great shows.

Keeping track of time during the day with the Mod Watch from the Timex x Todd Snyder collab. Natural Diplomat Boots by Thursday Boots. Slim Light Mercer Denim by Mott & Bow.

Keeping track of time during the day with the Mod Watch from the Timex x Todd Snyder collab. Natural Diplomat Boots by Thursday Boots. Slim Light Mercer Denim by Mott & Bow.

Lest we think the day was all about the big-ticket items (and bands), small touches really do go a long way in completing an outfit, such as the Hudson Belt from Arcade Belt Co. It’s made with stretchy, comfortable and durable navy smartweave fabric, and the color worked well alongside my socks, the lightweight, breathable, teal-and-grey color-blocked Troubadour from the team at Richer Poorer. Those socks paired with my boots for an added touch of comfort, and that was crucial — it felt like a long run-up into the evening, but it really was worth it.

That brings us back, once again, to The National. While I certainly looked forward to dressing for the day in style and checking out other great acts, I’d been looking forward even more to seeing the hallowed indie rockers return (relatively close) to their home turf. Seeing them two years ago at Calvin College back in my home state of Michigan was, to be quite honest, a lifechanging show (right up there with seeing Lucius at Daryl’s House Club in upstate New York earlier this year). And this time around, The National absolutely didn’t disappoint. Although the entire set was stellar, early renditions of “Don’t Swallow the Cap” and “Afraid of Everyone” were huge crowd-pleasers, as was an uptempo take on “Sea of Love” off of the acclaimed Trouble Will Find Me. Being that close to the stage for those songs was epic, seriously. The Dessner brothers are one of the tightest guitar duos around, and the Devendorf brothers reliably carry the rhythm section, too. What more can you ask for?

They’ve got a discography that’s so deep and versatile, an hour isn’t nearly enough — even at a festival.  A soul-stirring rendition of “Bloodbuzz Ohio” played well off of two new songs, “The Day I Die” and “Find A Way” fit right in with the rest of the band’s live set, which also managed to work in “England” off of High Violet. The variety in their setlist means you might hear your favorite track at an unexpected time, and it means you might have to wait a bit longer, too. “Fake Empire” was distinctive and well-done, cueing up the crowd for an intense, loud version of the classic “Mr. November” (just ask the folks next to me how much I enjoyed that one). Although Mr. Berninger stayed on stage for that song, he made his way into the crowd for “Terrible Love” — I’m surprised the fans let him go! It was nothing short of emotionally stirring and incredible, probably worthy of a full blog post in its own right. It was a two-year wait to see them, but I can only hope less time goes by before I see them again.

If you get the chance to check them out at one of the many festivals they tend to play during the summer, please do. The same goes for their friend and a top-billed act in his own right, Sufjan Stevens. It was time to put away those sunglasses (and grab another round), as he powered through a visually stunning set — both The National & Sufjan could definitely play for twice as long, what with their deep discographies and high-energy stage shows. Of course, an act like Kendrick Lamar is a huge crowd-pleaser and puts on a high-energy stage show of his own, which drew by far the largest crowds of the day.

It was a heck of a day that really was packed top-to-bottom — bands like Oh Wonder and Foals also rounded out the day nicely with afternoon sets that fit with the festival’s more eclectic vibe. Attendance felt a bit light at times, but it provided the chance to grab some prime real estate during killer sets by some of my favorite acts (particularly, as we all know…. The National). And gear like my durable Thursday Boots Natural Diplomat Boot and the Timex x Todd Snyder Mod Watch was really crucial to taking on such a hot and busy day in style. It was such an honor and privilege to be able to see a renowned act like The National, and the rest of the lineup definitely didn’t disappoint. We’ll see if Panorama sticks around next year, but if they continue to curate an eclectic lineup packed with big names and solid variety, there’s a great chance it will be — and I’ll be there with my best menswear to rock out!

‘Til the next show,

-Beau

Huckberry

#OOTD: How to Style Twill Pants with Savane

Editor’s note: The following post is brought to you by Savane. The Style Guide only works with and/or promotes brands and products used and enjoyed by its author.

Stepping out on a busy day with the Premium Flex Twill Pant from Savane. Trucker Jacket by JackThreads. Slim chambray shirt by Old Navy. Brown Scout Chukka Boots by Thursday Boots. Waterbury Chrono from the Timex x Red Wing Heritage collab.

Stepping out on a busy day with the Premium Flex Twill Pant from Savane. Trucker Jacket by JackThreads. Slim chambray shirt by Old Navy. Brown Scout Chukka Boots by Thursday Boots. Waterbury Chrono from the Timex x Red Wing Heritage collab.

Today’s #OOTD post is switching things up from the norm — and in this case, that’s a very good thing. Perhaps in your daily life, you find yourself on the go a lot — be it work, play or travel. That’s the case for myself as well, as  I’ve been traveling quite a bit this summer between busy days in NYC (we’re talking days at the office followed by trips around the country, including a Memorial Day weekend upstate ). So when Savane approached me as part of my writing for the Men’s Health MVP Network , I knew the brand’s twill pants were worth checking out as part of my active, everyday life . If you’re unfamiliar with Savane, they offer up everything from suit separates to dress shirts to the twill pants you see here (and you can find them everywhere from Amazon to JCPenney ). It’s around-the-clock wear that works particularly well to hit the office, have lunch in the park and head out to a networking event thereafter.

Take twill chinos from Savane, add American Trench striped socks, leather chukka boots from Thursday Boots, and a tough leather watch from the Timex x Red Wing collab.

Grab a sharp brown leather messenger bag then take twill chinos from Savane, add American Trench striped socks, leather chukka boots from Thursday Boots, and a tough leather watch from the Timex x Red Wing collab — you’re set for work &  play.

Given the need to dress in versatile style to transition from setting to setting, I rocked the brand’s Premium Flex Twill Pant in Ermine. They’re a reliably classic pair of pants that paired up nicely with my classic Old Navy blue chambray shirt and other personal favorites, like my durable Thursday Boots Brown Scout Chukka Boots and some stylish and continental Sunday Somewhere sunglasses. To finish the look off, I grabbed my durable leather watch from the Timex x Red Wing collab — all of the above are pieces that work seamlessly together for work or play. Of course, complementing those pieces with other sharp accessories, like a striped webbed J. Crew Factory belt, was essential, too.  However, the anchor of the whole outfit were the  comfortable and sharp Premium Flex Twill Pants. They’re tailored in a straight-tapered cut but offer room to move around in, a great thing for all you active fellas out there. And they worked seamlessly to take me from the office to a networking event later that night. They could even be styled in a manner similar to this #OOTD (that is, with a chambray blazer and sneakers). During both hot and cold days to come around NYC, I’m sure they’ll work just as well. For more on Savane, head here, and swing on through The Style Guide tomorrow for a look at the best men’s dive watches to buy right now.
Until then — stay stylish,
-Beau

Buck Mason - Timeless Design. Made in America.

Summer style: Attending a Michigan wedding

Editor’s note: Click here for more tips  how to dress for a summer wedding.

Dressed in style for a summer wedding. Blue shirt by Twillory. Cotton tie by Ties.com Thompson Navy suit by J. Crew Factory. Glasses by Warby Parker. Heritage Tassel Loafers by Sebago. Brown leather watch by MVMT Watches.

Dressed in style for a summer wedding. Blue shirt by Twillory. Cotton tie and navy tipped pocket square by Ties.com Thompson Navy suit by J. Crew Factory. Glasses by Warby Parker. Heritage Tassel Loafers by Sebago. Brown leather watch by MVMT Watches.

It’s a topic that’s come up before here on The Style Guide — that would be, dressing for a summer wedding — but this past weekend presented the perfect opportunity for yours truly to put some of those ideas into practice.  Following a whirlwind, busy New York Fashion Week: Men’s (an exhausting but super-fun week), I hit the road back to Michigan to attend the wedding of my great friend Matt Sheehan, a former State News colleague and another proud & sports-obsessed Spartan (watching games was either very fun — or not so fun, depending on how MSU fared). In fact, Matt & I took in a particularly momentous MSU football game last fall, and caught up during my spring trip to Florida. That being said, it was still great to make the trip back. It was a truly lovely wedding, and so great to reconnect with amazing friends back home in the process. With fashion week done, it was also awesome to get away from the bustle of NYC for a  bit, and even better to do so during a beautiful Michigan summer — as always, even with a humble weekender bag in tow, I tried my best to pack the best #menswear gear I could round up.

A full bag ready to hit the road. Voyager Waxed Weekender by Owen & Fred. Beachcomber Chambray Shirt by Bourbon & Blue. Staple Denim made in Italy by Mott & Bow. Brown Scout Chukka Boots by Thursday Boots. Striped socks by American Trench. Waterbury Chrono from the Timex x Red Wing collab. Adventure Log by Word Notebooks. Brown leather belt by J. Crew. Chapter Travel Kit by Herschel Supply Co. Moisturizer by Tread for Men. Maximus Sunglasses by Sunday Somewhere.

A full bag ready to hit the road. Voyager Waxed Weekender by Owen & Fred. Beachcomber Chambray Shirt by Bourbon & Blue. Staple Denim made in Italy by Mott & Bow. Brown Scout Chukka Boots by Thursday Boots. Striped socks by American Trench. Waterbury Chrono from the Timex x Red Wing collab. Adventure Log by Word Notebooks. Brown leather belt by J. Crew. Chapter Travel Kit by Herschel Supply Co. Moisturizer by Tread for Men. Maximus Sunglasses by Sunday Somewhere.

That started with some essential everyday carry accessories that have quickly become personal travel favorites — such as my tough, sturdy Owen & Fred Voyager Waxed Weekender Bag. It’s accompanied me on nearly every trip I’ve taken as of late, and with dependable Wickett & Craig leather handles, quality hardware and a surprising amount of room, it’s taken the toils of the road quite well. I packed some key everyday carry accessories, including my Word Notebooks Adventure Log and Herschel Supply Chapter Travel Kit; just as small details finish off an outfit, so too can they upgrade even the things you don’t quite think about when traveling. For the flight to Michigan, I pulled some double-duty, wearing a Bourbon & Blue short-sleeve chambray shirt and pairing it up with my J. Crew Factory Thompson suit jacket and some tailored Savane twill pants (look for more on those pants in a special Tuesday post).  For outfits throughout the weekend, my Thursday Boots Brown Scout Chukka Boots helped me travel in style — always a must! I finished off the look with one of two watches I brought along for the weekend — my personal favorite, the rugged and durable Timex x Red Wing Waterbury Chronograph.  If you can only fit in one or two watches as part of your packing list, it’s tough to go wrong with a really well-built watch that works for more casual or slightly more dressed-up ensembles. With any travel, stylish sunglasses are a must — for both tailored wear and my casual ensembles, I’ve found myself consistently reaching for the pricey but sharp Maximus sunglasses from Sunday Somewhere.

While I was excited to hit the road, I ran into some unfortunate travel delays leaving New York that left me stuck at the airport all day — so unfortunately, I missed out on a classic Michigan backyard barbeque. Luckily, I still made it back in time for a nice Saturday and the wedding itself! It goes without saying that I had an incredible time, and was very glad to have made the trip back (CONGRATS, MATT AND SAM!). Of course, I was glad I brought along a trusty suit, as well. Packing the appropriate gear to get you through a warm-weather wedding is a bit tricky. While it might seem at first too hot to rock anything but a lightweight linen suit, if you have to grab one suit for all four seasons, worsted wool in a neutral color like navy is a very solid option. It’s a more breathable and classic fabric, and in a slim, tailored (and affordable) cut like the J. Crew Factory Thompson Suit, it’ll work well with a crisp dress shirt, and with or without a tie even if you don’t have a wedding to attend. In fact, my shirt was a favorite of the outfit in terms of fit and construction — it’s on-sale now, so I’d definitely recommend you pick up the nicely tailored Twillory Non-Iron Blue Twill Shirt which paired up well with the navy suit. The accompanying J. Crew Factory suit pants went along just fine with the jacket, as they feature a nicely tailored fit that isn’t quite as slim as the J. Crew Ludlow, so that works nicely for most body types — having the belt loops removed, as I did, makes for a super-clean and crisp look, too.

This past weekend's wedding outfit laid out and ready to go. Navy Thompson suit by J. Crew Factory. Blue shirt by Twillory. Cotton tie and tipped pocket square by Ties.com. Brown leather watch by MVMT Watches. Heritage Tassel Loafers by Sebago. Wallet from the latest SprezzaBox.

This past weekend’s wedding outfit laid out and ready to go. Navy Thompson suit by J. Crew Factory. Blue shirt by Twillory. Cotton tie and tipped pocket square by Ties.com. Brown leather watch by MVMT Watches. Heritage Tassel Loafers by Sebago. Wallet from the latest SprezzaBox.

And stylish accessories are a must to finish off any suit. In this instance, a cotton tie in a unique, summer-friendly color and a navy tipped pocket square courtesy of the team at Ties.com paired well with one of my favorite suits (Editor’s note: I own approximately one all-season, every-occasion suit — and it’s this one). Seriously, as a competitor and an alternative to The Tie Bar, the selection and pricing at Ties.com is quite on-point (and y’all know that if it wasn’t, they wouldn’t have made the cut — right?). For the warm weather, I slid into a refined pair of Sebago Heritage Tassel Loafers, featuring an oily waxed leather (as the site implies) that’s shown age and wear marks beautifully after only a few weeks of wear (check out another way to style them here). Of course, if you don’t have room in your bag for another pair of shoes (and I barely did), I’d recommend reaching for perhaps the above brown chukka boots to pull double-duty. And although my Timex x Red Wing Waterbury Chrono worked suitably well for casual situations, I was too tempted not to reach for one of my favorite everyday watches, the MVMT 40 in Blue/Brown Leather — it’s a watch that’s really a great value for the quality and wearability (although one of my New Year’s style resolutions was to wear less blue, I can’t seem to stop wearing it). Pieces that can work with everything from a tee and shorts to a suit are the best sort of travel style essentials to pack when space is limited.

Sunday's outfit grid for a day of travel back from Michigan. The Jack in Indigo Star Shirt by Taylor Stitch. Slim grey selvedge denim by Billy Reid. White Legend Sneakers by SeaVees. Waterbury Chrono from the Timex x Red Wing Heritage collab. Adventure Log by Word Notebooks. Vintage ballcap by Goorin Brothers.

Sunday’s outfit grid for a day of travel back from Michigan. The Jack in Indigo Star Shirt by Taylor Stitch. Slim grey selvedge denim by Billy Reid. White Legend Sneakers by SeaVees. Waterbury Chrono from the Timex x Red Wing Heritage collab. Adventure Log by Word Notebooks. Vintage ballcap by Goorin Brothers.

With an incredible wedding and an incredible evening in metro Detroit in the books, it was time to catch a flight back to Michigan that felt a bit earlier than I’d have preferred after a full week of fashion shows and travel. Reaching for grab-and-go pieces that work in a pinch is still a must even if you’re jet-lagged, so my Taylor Stitch Jack in Indigo Star Shirt (very low in stock at the moment, unfortunately) worked out very well — I’d recommend you bring along a solid blue chambray shirt for similarly versatile style.  Although it was hot, a pair of Billy Reid grey selvedge denim did just fine when paired with one of my favorite pairs of sneakers, the SeaVees Legend Sneaker — when in doubt, classic white sneakers are just the way to go. As was the case the rest of the weekend, my stylish Timex x Red Wing Waterbury Chrono worked sufficiently as I hauled my gear to the airport (and it helped me catch my flight on time!).

While it’s always nice to be able to bring along my favorite style essentials when I travel, it’s even better to know that at the end of the road on trips home, there are great friends and great times waiting — truly, it’s something for which I’m very thankful, and it’s got me eagerly awaiting my next trip to Michigan. No matter what’s in my bag, I know I’ll always look forward to going back.

If you have questions on what to pack for your own travels, tweet at me or catch up via The Style Guide’s Facebook page.

‘Til the next trip,

-Beau

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#OOTD: How to Style A Henley for Summer

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

To me, there isn’t a style of shirt (without a collar, that is), that’s more versatile or rugged than a great short-sleeve henley. Although expressions of style and masculinity are changing all the time, there’s no doubt that a stylish henley is a still a reliable go-to if you want to upgrade your game and look a little tougher and stronger — or simply better in general — and that’s certainly true for the below tips on how to style a henley for summer. That goes for long-sleeve henleys with a vintage look, and it goes for fashionable short-sleeve henleys fit for fighting the warm weather. The button placket on well-made henleys adds some nice visual interest to looks both casual and a bit crisper, and in the right fit and color (like the slim-fitting indigo henley) below, you can wear the piece on its own with slim chino shorts or layered up under an unconstructed blazer for unique high-low style that can go to the office on a casual day and out on a date thereafter (I bet you’ll look  better than the fella in the ill-fitting suit — trust me). It can be a bit of a process to switch from a plain white tee to a knit with more texture, color and visual details (even if it is just a simple button placket). But those added small details make it a worthy style upgrade — especially when you ditch the long sleeves in favor of a piece that’s just as trim-fitting, yet a heck of a lot more ready for the warm weather. Invest in one that’s well-crafted and you can rock it under a spring jacket, beneath a fall blazer or as a complement to a warm shawl cardigan in winter. For now though, focus on great chinos, solid suede boots and other accessories just begging to be worn on a warm summer’s day. Chime in on the #OOTD discussion at our very own Style Guide Facebook page, and we’ll see you out shopping.

Pair a short-sleeve henley with staples you might already have in your closet, like stone chinos and suede chukka boots.

Pair a short-sleeve henley with staples you might already have in your closet, like stone chinos and suede chukka boots.

The Henley: Jason Scott Banks Short-Sleeve Henley in Indigo — $96: Nearly $100 is a certainly a steep price to pay, but that price gets you exceptional quality, terrific Peruvian fabric and finishing touches like antique metal buttons on the placket.

The Chinos: Taylor Stitch Slim Chinos in Light Stone — $98: Taylor Stitch chinos have been a Style Guide favorite for some time now, and the reliably ideal fit and excellent fabric quality and color make these a fine match for that indigo henley.

The Boots: Thursday Boots Honey Suede Scout Boot — $149: Just as with those Taylor Stitch chinos, the Scout Boot from Team Thursday has received positive reviews in this neck of the woods, for comfort and quality as much as looks. This rich Honey Suede pair really does have it all.

The Socks: American Trench Edo Collection Socks — $19.50: Nearly $20 for a pair of socks? You’re darn right, and they’re some of the best (if not the best) ones you can rock that are made in America at family mills. Plus, the color pops just the right amount against the faded indigo henley.

The Belt: J. Crew Factory Double-Striped Webbing Belt — $14.50: Again, it’s a little counterintuitive that a belt would cost less than socks, but this piece is a bargain number that can be styled into several looks (see my Instagram for more examples, will ya?)

The Sunglasses: J. Crew Jack Sunglasses in Silver Navy — $98: As first seen on this site’s roundup of the best men’s sunglasses for summer, this pair of aviators is simple yet sleek and stylish (not to mention pretty cost-effective).

The Trunks: Tommy John Second Skin Titanium Trunk — $32: More than $30 sure is a heck of a lot to pay for underwear, but with what Tommy John can deliver in terms of quality, it’s worth it. The Dark Titanium color  shown here has sold fast, but check out their other colorways here.

The Watch: Timex x Red Wing Waterbury Chronograph — $158: Timex and Red Wing really have thrown everything they’ve got at this standout watch, with a  strap crafted from rugged Red Wing boot leather and a sturdy, classic-looking dial that’s super-functional and ready for just about anything (including NYC style adventures).

Sure, chinos and a henley might seem like a simple outfit combination at first glance, but it’s the upgraded, slimmer fits, richer colors and better quality that make this look acceptable for everything from grabbing beers at the bar to leaving early on a casual Friday (perhaps with a light grey blazer, if I do say so myself). And the other pieces in this ensemble, from a warm-weather friendly cotton belt to suede chukkas, can work in multiple seasons. Finally, there’s truly no bad time for a durable leather watch or a subtle-yet-stylish socks or crisp sunglasses. Making these pieces work in your favor by adding a lightweight sweater or swapping in a stainless steel dive watch is definitely going to pay style dvidends. Do we read each other loud and clear? Yes? Excellent.

‘Til next time!

Stay stylish,

-Beau

Frank & Oak

Florsheim
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#OOTD: How to Style Leather Chukka Boots

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

As I’ve so often written about on The Style Guide, style doesn’t have to be too taxing or complicated. It’s not about chasing too many trends (things like athleisure and ridiculously distressed clothing come to mind), but I find that it’s about taking basic pieces and making them work for you by nailing the fit, texture and color. And if you stock a wardrobe full of versatile, casual pieces, that’s a job that can be taken care of quite easily. Take the below #OOTD. It’s perhaps endlessly versatile, from a first (or second, or heck, third) date to a day at the office to weekend brunch or shopping. That’s what you get when you focus on pieces that are relatively classic and dial in the fit and proportions to make them work for you. So in the case of the chambray shirt you’ll see below (spoiler!), that means looking for a piece that fits trim and flatters your frame. The same goes for the chinos on display. When you check those boxes off, it then gets easier to focus on other crucial areas – like pattern and color (or, grabbing a great pair of essential chukka boots). With all that being said, let’s not waste another moment! Onto the #OOTD below.  Hit me up on Twitter or Facebook if you like what you see!

Taking a classic pair of brown leather chukka boots and pairing them with style staples -- simple, effective and sharp!

Taking a classic pair of brown leather chukka boots and pairing them with style staples — simple, effective and sharp!

The Boots: Thursday Boots Brown Scout Boot, $149 — While plenty of brands make a solid leather chukka boot (see here for one option), it’s tough to find a brand that’s nailing a solid price point for even higher quality.

The Shirt: Old Navy Slim-Fit Chambray Shirt, $25 — Because we’re starting with the boots and building from there, a solid, reliable and remarkably affordable chambray shirt is for sure the way to go.

The Chinos: Bonobos Jet Blue Washed Chinos, $88 — Again, navy chinos are classic, reliable (saying that a lot, aren’t we?) and well-fitting — particularly with your pick of three fits. The navy blue plays nicely off the chambray, too.

The Socks: Pair of Thieves Splelurking Socks, $10 — You might recognize this brand from a past Style Guide #OOTD, and this pair is a nice way to break up the shades of blue between the chinos and chambray shirt.

The Belt: J. Crew Factory Braided Leather Belt, $27.50 — Playing off the adage that simple is better, this relatively affordable and durable belt breaks up the outfit with solid texture and keeps things casual yet crisp.

The Watch: Timex Weekender Fairfield Watch, $75 — A new introduction from a brand that’s really upped their design as of late — the casual nature of this outfit means you needn’t worry about matching the leather to the chukkas all that much.

The Money Clip: Owen & Fred Brass Money Clip, $19 — If you live by the principle that style is in the details, this money clip streamlines your everyday carry and looks great in the process.

The Bag: Owen & Fred Flight Brief, $245 — If you prefer a larger bag, this might be a bit small for you. However, if you prefer to keep things simple, sharp and stylish, picking up this flight brief is a great investment.

And with all of that, we’re set. This outfit isn’t tremendously groundbreaking, and it’s not build to turn all that many heads in terms of street style. But it’s sharp, effective and versatile — be it going from the office to a weekend trip, or out and about on the weekends. Pairing shades of blue is a personal favorite of this menswear writer (although I’m trying to mix up those colors!), so it’s a tried-and-true combination. And crucially, starting with a remarkably handsome pair of shoes — chukka boots in this case — is always a solid bet no matter what occasion you might be dressing for. Be sure to take care of them with brown leather shoe cream or polish, and they’ll stand up to everything from tailored wear to a casual weekend outing.

Are you a fan of this week’s #OOTD? How would you style brown leather chukka boots?

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Florsheim

Capital Style: A spring weekend in Washington, D.C.

washington-dc-edited-photo

Just the right staples for a spring weekend in Washington, D.C. The Jack in Indigo Star Shirt by Taylor Stitch. Hayden Grey Jacket by Bridge & Burn. Dark blue denim by Mott & Bow. Chariot Runner Sneakers by Brooks Heritage.

 As I hinted at in this past Friday’s weekly reading roundup, I had the chance to travel just a few hours south via train to Washington, D.C. visit my great friend and former college roommate Ian Kullgren this weekend — and a lovely weekend it was. As it were, the last time we saw each other was back in East Lansing after graduation (home of our Michigan State Spartans). So, we had a lot to catch up on! Although the forecast threatened rain initially, the skies cleared up throughout the weekend and we were able to see a ton of Washington, D.C. I’d been to our nation’s capital back in November, but this time, the trip it was different – it was thankfully a lot warmer and sunnier, for one. And there was more to see given Ian’s location in the Woodley Park neighborhood of the city. So as the week wrapped up, I planned out what #menswear to pack and hit the road – planning ahead based on the weather and itinerary is something that’s gotten easier for me as time has gone on, (and hopefully, it’s the same for you!).

Easygoing gear for a weekend of adventures. Waxed Voyager Weekender by Owen & Fred. Legend Sneakers by SeaVees. Stringer Dune Shorts by Bridge & Burn. Sunglasses by Tom Ford. Navy leather card case by Issara. Brown leather watch by MVMT Watches.

Easygoing gear for a weekend of adventures. Waxed Voyager Weekender by Owen & Fred. Legend Sneakers by SeaVees. Stringer Dune Shorts by Bridge & Burn. Sunglasses by Tom Ford. Navy leather card case by Issara. Brown leather watch by MVMT Watches.

Having traveled to some pretty neat places across the past handful of months (including a stylish weekend in Florida and a trip to Detroit), I knew a great bag was definitely needed for this particular trip — we’re talking something that can hold up trip after trip (and you should look for a similarly durable piece). Owen & Fred’s new Voyager Waxed Weekender, as seen above, more than fit the bill. It’s sturdy as heck, made in the USA and finished off with tough 9 oz. leather straps from one of America’s oldest tanneries, Wickett and Craig. Seriously, this bag is a beast, and I could definitely go on — but the rest of the trip calls! (Look for a full feature on the piece in this site’s Style Pick of the Week series soon).

After a quick train ride down to D.C., we still had enough time on Friday to check out some D.C. haunts with our friend and fellow Michigan State Spartan Emily Wilkins. Our mini bar crawl of sorts took us to the always-great Capitol Lounge (an MSU haven) and the renowned Little Miss Whiskey’s, with enough rare beer on tap and in bottles to make your head spin. We grabbed a nightcap (hot dog, that is) at the renowned Ben’s Chili Bowl – that’s a great chili dog right there.

A casual, cool outfit for exploring Washington, D.C. Hayden Gray Jacket by Bridge & Burn. Indigo Denim Jack Shirt by Taylor Stitch. Dark denim by Mott & Bow. Chariot Sneakers by Brooks Heritage. Pilot's watch by AVI-8. Vintage ballcap by Goorin Brothers.

A casual, cool outfit for exploring Washington, D.C. Hayden Gray Jacket by Bridge & Burn. Indigo Denim Jack Shirt by Taylor Stitch. Dark denim by Mott & Bow. Chariot Sneakers by Brooks Heritage. Pilot’s watch by AVI-8. Vintage ballcap by Goorin Brothers.

Saturday proved a busy day that took us around D.C. on foot for long periods of time – in that respect, I was glad I packed comfortably and with versatility in mind (like the outfit you see at the top of the page!). For exploring everywhere from the National Mall to the bustling 14th and U Street areas, I grabbed some extremely comfortable (and sharp) navy, light blue and red suede sneakers from the Brooks Heritage line — the sport-inspired lifestyle line from Brooks Running. While the pair you see here is now unfortunately sold out, there are plenty of versatile options to be had — and something clean and simple like the GREATS Rosen Runner would also work just as well for travel adventures.

The lightweight, comfortable Hayden Gray Jacket from Bridge & Burn topped off what’s perhaps my new favorite shirt, the Jack in Indigo Star from the fine folks at Taylor Stitch — versatility is key when traveling for a quick weekend trip, and this shirt (just like a classic chambray shirt) definitely nailed it. And no matter where you go, some crisp and classic dark denim is always a solid bet — particularly if inclement weather is potentially in the picture. I grabbed a pair that’s a personal favorite, my Mott and Bow Skinny Mosco denim (the brand also stocks classic dark denim in other cuts, too). They’re simple, slim-fitting and particularly effective for a casual trip.

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We covered a lot of ground, from strolling through the Sculpture Garden at the National Gallery of Art to marveling at the National Archives and the Declaration of Independence – the first time I’d been back there since my 8th grade class field trip (no blog post covering that trip, sadly). We also made time to meet up with two old college friends (Go Green!), Gabby Saldivia and Colin Marshall, both talented folks who work at NPR – being around so many communications pros reminded me why I picked up that degree in the first place! If you fancy gobbling up some gourmet brews and delicious bites, Glen’s Garden Market is the place to do just that.  A post-dinner drink was definitely in order, this time at Smoke N’Barrel. Although we didn’t eat any of the restaurant’s famous barbeque, it looked mighty tempting.

Sunday's outfit grid for D.C adventures -- a Pima Crewneck Tee from Mack Weldon, Slim Light Mercer Denim from Mott & Bow and Brown Scout Chukka Boots from Thursday Boots. Customized Fairfield Watch by Timex.

Sunday’s outfit grid for D.C adventures — a Pima Crewneck Tee from Mack Weldon, Slim Light Mercer Denim from Mott & Bow and Brown Scout Chukka Boots from Thursday Boots. Customized Fairfield Watch by Timex.

For the rest of the trip, I brought along another trusty pair of denim from Mott & Bow, the all-new Light Mercer. Think of these as a step down from chinos and a …. step sideways from dark denim in terms of color and texture. That is, they can be dressed up like chinos or dressed down like denim — but you get a lot of comfort either way. For Sunday explorations, I also threw on a comfortable Mack Weldon Crewneck Tee. It’s admittedly simple and minimal, but the tee is comfortable and a great match for the color of the light denim. Crucially, the combo was also the perfect match for a terrific pair of Brown Scout Boots from the always on-point team at Thursday Boot Company.

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During my last trip to Washington, D.C., I also brought along a pair of chukkas from the brand, but I swapped out the Chocolate Suede Scout Boot for the brown leather boots you see here — and I was just as pleased with the results. They took me seamlessly around the city all throughout Friday night and on Sunday. The sturdy rubber sole of that chukka definitely helped for lots of on-foot trekking (and bar-crawling, if we’re honest with ourselves).I closed out Sunday with a quick stop in the D.C. outpost of Frank & Oak, one of my favorite men’s lifestyle brands — that was a real treat! And it was great to be able to grab a quick afternoon coffee at The Wydown, one of the city’s best coffee shops.

Sunday done right in D.C. Pima Crewneck Tee by @mackweldon. Slim Light Mercer Denim by Mott & Bow. Sunglasses by Tom Ford. Customized Fairfield Watch by Mott & Bow.

Sunday done right in D.C. Pima Crewneck Tee by Mack Weldon. Slim Light Mercer Denim by Mott & Bow. Sunglasses by Tom Ford. Customized Fairfield Watch by Timex.

Packing for any trip also requires some attention to the little things, the same sort of accessories you might wear at home — namely, a stylish casual watch or two. I was definitely pleased with the versatility and durability of my new AVI-8 Flyboy (similar to the model shown in the link), complete with a black leather strap that matched up just fine with my suede sneakers. And whenever I travel, my trusty MVMT Watches 40 Timepiece is also a frequent companion. Plus, my new Timex Weekender Fairfield (seen above) is sharp, stylish and a terrific value. A minimal leather watch can pair with everything from navy sneakers to brown chukkas, and it works with a blazer and khaki chinos if your travels call for something a bit more polished. So given the laidback nature of this trip, it worked more than fine for both travel and exploration.

I also prefer to bring along finishing touches that can make all the difference between traveling in comfort and, well… not traveling in comfort. In this instance, that means my dependable dopp kit from the Byrd x Richer Poorer collaboration, as well as a few everyday grooming essentials from the always-reliable Baxter of California. And additional pieces like a great pair of Mack Weldon boxer briefs and stylish-yet-understated American Trench socks weren’t overlooked in my bag — and they shouldn’t be in yours, either.

As trips like these tend to go, it felt a bit too brief (such is life when trying to coordinate around the schedules of a journalist and a PR guy!). But I really felt like I was able to experience much more of the city than in past trips, from a stop through the National Archives that gave me some great historical perspective, to a walk through the National Gallery of Art and time spent along the bustling, hip U Street area. It’s a city that’s more varied than meets the eye – it’s not all tour groups and national monuments (although seeing those monuments made me feel pretty patriotic). There’s a burgeoning menswear scene, the dining (and local craft beer selection) is on-point, and it’s quite easy to get around – that’s just a handful of the major pluses I experienced in a quick weekend. I’d say it’s absolutely worth a visit – and if you’ve been before or you live there, you already know that! I’ll be back again. Until then, look for more on The Style Guide tomorrow covering a stylish spring outfit suggestion.

Thanks for reading!

-Beau

Florsheim

#OOTD: How to Wear a Suit This Spring

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

For every situation that calls for more casual, rugged wear — like how to dress for a spring bar crawl, for instance — there are situations that call for a bit something more: Say, a big presentation at the office, or a (very) fancy dinner date. That’s what we’re tackling today on The Style Guide, with an eye specifically toward how to do it right — after all, rocking a shirt and tie sans jacket just isn’t something that’s going to leave most of us looking our best. The thing with investing in a suit — even a budget-friendly option like the below — is that you can get a lot of wear out of it (yes, even casually).  But today’s post goes for a full-on, suited look. Shop away! And if you have suggestions for an #OOTD scenario you’d like covered, let me know on Facebook!
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Taking a few classics -- like the worsted wool suit -- and flipping them by incorporating unique texture and color.

Taking a few classics — like the worsted wool suit — and flipping them by incorporating unique texture and color.

The Suit: J. Crew Ludlow Harbor Blue Suit Jacket in Italian Worsted Wool, $425 — J. Crew just absolutely knows what works in terms of classic, affordable suiting — and the Harbor Blue color of this jacket is a terrific change of pace if you’ve already got a navy suit in your closet. As always, don’t forget the Ludlow suit pants (which should fit relatively slim and modern).

The Shirt: Taylor Stitch White Royal Oxford, $98 — Who knew that Taylor Stitch made dress shirts? This guy sure didn’t. You’re getting exceptional quality for an exceptionally classic piece that can go anywhere. If you want something more price-conscious, head this way.

The Pocket Square: SprezzaBox White & Tan Pocket Square, $16 — In addition to a neat monthly subscription service, SprezzaBox also makes its own line of essential ties & accessories — slightly more expensive than The Tie Bar, but with great styling potential.

The Tie: SprezzaBox Knit Charcoal Shifting Tie, $25 — A charcoal knit tie is virtually foolproof when it comes to rocking with all manner of suits across all seasons — that holds true for spring, as well.

The Shoes: Thursday Boots Brown Scout Boot, $149 –A pair of leather chukka boots with a suit? Heck yes. The heightened blue color of this suit, along with the more textured charcoal knit tie, pushes this look into more casual territory, so the boots just work.

The Belt: J. Crew Factory Reversible Brown Leather Belt, $27.50 — A tried-and-true leather belt that serves a double function is the way to go here — you get J. Crew quality for less, too.

The Socks: Mack Weldon Total Eclipse Blue Socks, $12.50 — For a brand that does basics like its slim merino long-sleeve tee so well, they sure do know how to make comfortable socks that are still slightly cheaper than what you’d find  at other retailers.

The Watch: Daniel Wellington Classic Bristol Silver Watch, $229 — A timeless watch from a brand that just gets how to do things right; it’s slim, minimal and tremendously stylish!

That brings us, once again, to the end of another #OOTD — taking pieces that you should probably already have in your wardrobe (the classic, four-season worsted wool suit, for one) and injecting some new color and texture helps shake things up nicely. The color combination of the tan tipped pocket square and the charcoal knit tie is another variation on the traditional silk tie, and the brown leather chukka boots are a heck of a deal for the quality. Other hardworking pieces, like breathable socks and a slim dress watch, just work regardless of the season. This ensemble will hopefully work for all kinds of dressy scenarios — be it a dressy summer wedding or a dressy day at the office. And on a more casual front: Coming up tomorrow, we’ll be tackling the best short-sleeve shirts to rock this summer.

Thanks for reading, and stay stylish!

Florsheim

Online Shopping Picks: Best Suede Chukkas to Buy For Spring

Editor’s note: To learn more about great gear to buy for spring, click here.

Suede chukkas work in plenty more seasons than one. Read on for more details on the pair at left. Image courtesy of Huckberry.

Suede chukkas work in plenty more seasons than one. Read on for more details on the pair at left. Image courtesy of Huckberry.

As soon as the calendar really gets rolling into spring, there are certain items I’m anxious to shelve — and certain items that I’m ready to keep on wearing (or at least, wear more). One of those such items is the versatile suede chukka — it’s arguably a three-season shoe, well-suited to the colder temperatures of fall but providing some nice textural difference from shiny leather shoes during the sunnier days of spring and summer. When it gets snowy is when it’s tough to put ’em away — but now that those days are (hopefully) long gone, it’s time to break ’em out more. So that’s what we’re getting into here. The texture isn’t the only great thing about a suede chukka — the ankle cut of a classic chukka boot makes it the perfect go-between from, say, a lightweight, low-cut sneaker and a thicker winter boot — that means they’re ideal to style with everything from slim stone chinos to some rolled lightwash denim. They come in both casual and slightly more formal iterations, too. And that’s just the tip of the iceberg! Peep the full set of picks below, and let me know on Facebook if you think I missed any key brands.

Stay stylish!

#1. Thursday Boots Honey Suede Scout Chukka Boot — $149

Eye-catching honey suede from Thursday Boots makes this pair of chukkas a stunner.

Eye-catching honey suede from Thursday Boots makes this pair of chukkas a stunner.

Finding a well-made, reliable chukka (especially in a rich shade of honey suede) is a somewhat tricky endeavor, but Thursday Boots delivers again with its durable Scout Chukka. This writer has a pair of the Scout Chukkas in Chocolate Suede, and if the quality is anything like those, the Honey Suede version should hold up handsomely. The slightly higher-than-normal ankle cut is a continental touch, the studded rubber sole is tough on the ground yet comfortable on your feet, and in this instance, the honey suede is a colorful hue that’ll look great with slim white denim now and even better under dark raw denim come fall.

#2. J. Crew Classic MacAlister Boots in Stone — $148

J. Crew's take on the classic style.

J. Crew’s take on the classic style.

For Thursday Boots taking the cake with its $149 chukka, J. Crew’s MacAlister Boot in Stone comes in a close second — at a very slightly cheaper price (ha!). This is certainly the more casual of the two boots, as this number has all the makings of a traditional desert boot (different from a versatile leather chukka). That goes for the traditional crepe rubber sole and continues on through the raised contrast stitching between the sole and the upper. This boot is still made in Italy, and it should certainly pack in all the quality one would expect from a pair of J. Crew footwear.  For weekend brunches and coffee runs (or a casual Friday), this is your go-to boot.


#3. Clarks Desert Boot in Wolf Suede — $130

An iconic silhouette rendered in a unique suede.

An iconic silhouette rendered in a unique suede.

One would be remiss to talk about desert boots or chukkas and not give a look toward Clarks, the originator of the style (for the general public, at least). The Wolf Suede Desert Boot takes the iconic Clarks silhouette and does it up in a beige suede that should make these another reliable, casual footwear option for a ton of situations — be it a fall coffee date (paired perhaps with a shawl-collar cardigan and denim?) or a spring weekday with a slim polo and chinos. Plus, the price and quality are both very hard to top among like-minded brands.

#4. Oak Street Bootmakers Chocolate Suede Campus Chukka — $426

Perhaps the most premium pair of suede chukkas on the market, totally ready for anything.

Perhaps the most premium pair of suede chukkas on the market, totally ready for anything.

Think a darker suede can’t be worn in the warmer months? Think again, my friend. If you’re on the hunt for a pair of chukkas that are worth the investment and the styling potential, the Chocolate Suede Campus Chukka from Oak Street Bootmakers is the chukka for you. It’s crafted in America with beastly construction, from the Goodyear welt to the waterproof suede (really), and the oiled leather soles. The color is rich and beautiful, equally fit for pairing with slim tan chinos now and your toughest pair of dark denim later this year.

#5. Astorflex Greenflex Chukka in Stone — $145

One seriously stylish and sustainable pair of desert boots.

One seriously stylish and sustainable pair of desert boots.

For the last entry on this list, we turn to a boot that combines all the inspiration of the classic desert boot with some seriously eco-friendly construction (be warned that it’s only available in sizes 9-12 right now, though). Yes, Astorflex certainly knows what it’s doing when it comes to combining quality, style and sustainability. This pair is made in Italy, yet rings up (or rather, charges your card) for an incredibly low price. The memory foam footbed should be comfortable, and the organically treated leather is processed slowly for more than a month, resulting in a pair of footwear that you can also feel good about buying.

So, picking up a new pair of footwear to add to your rotation doesn’t have to be an expensive or time-consuming process. Starting by looking for quality materials and versatile style potential is going to take you much further than settling for something less expensive — in that case, Florsheim’s Constable Chukka was also close to making the cut. If you’re uncertain about how to style a suede chukka, rest assured that it does just as well as a sharp leather chukka when paired with like-minded outfits — whether that’s a slim T-shirt and denim or a polo and lightwash jeans. If you play your cards right (and the weather holds out), it’s a style that could be in your rotation ’til fall.

Do you have a pair of suede chukkas in your closet? Which of the above pairs would you pick up for this spring?


The Product Review: Thursday Boot Company Diplomat Boot

Editor’s note: For a full set of product reviews covering everything #menswear — from watches to chinos — click here. Click here to shop boots, too. 

Getting out and about in NYC with the Color No. 8 Diplomat Boot from Thursday Boot Company. Slim tan chinos by Banana Republic. Striped henley by J. Crew Fisherman Cardigan by JackThreads. Merino watch cap by American Trench. Buffalo Bobber Leather Gloves by Iron & Resin.

Getting out and about at the High Line in NYC with the Thursday Boot Company Color No. 8 Diplomat Boot. Slim tan chinos by Banana Republic. Striped henley by J. Crew Fisherman Cardigan by JackThreads. Merino watch cap by American Trench. Buffalo Bobber Leather Gloves by Iron & Resin. Glasses by Warby Parker.

If you peruse the pages of this blog from time to time looking for the best boots for men, certain brands definitely tend to pop up consistently for their mix of affordability, dependability and, in the case of Thursday Boot Company, seasonality. Without a doubt, there are certain pairs of men’s boots that can’t be beat. That is to say, in the depths of winter for a lot us, you need sturdy, tough footwear that can carry you through slush and snow to your car (or the subway), and then wherever the heck else you might need to go — be it a concert, a date, you name it.  So that’s what we’re looking at today. The brand’s men’s boots have been featured here prominently before, including a review of the Chocolate Suede Scout Chukka and the dearly departed Roughout Captain Boot. First launched as a Kickstarter project not even two years ago, the brand continues to make splashes with well-timed and well-executed releases — including its more premium Black Label line and unique silhouettes like the hiker-inspired Commander. But one boot in particular is the focus of today’s post — the Color No. 8 Diplomat Boot.

Florsheim

The silhouette definitely calls to mind the classic Red Wing Heritage Moc Toe Boot, yet the Thursday iteration is sleeker and more refined. There’s something to be said for that, despite the fact that it’s a moc toe boot. This pair forgoes the classic yellow laces in favor of sleeker flat-wax laces, just as the Roughout Captain Boot. And the sleekness and quality of this pair for the price is evident as soon as you get them out of the box. Looking for a boot that’s just different enough than a captoe boot or a chukka boot — yet still versatile and sufficiently sharp — is a somewhat tricky endeavor, but these boots fill that void nicely.

Unboxing the Diplomat Boot from Thursday Boot Company. Big fans of these guys.

Unboxing the Diplomat Boot from Thursday Boot Company. Big fans of these guys.

Crucially, they make use of renowned Horween leather in that covetable Color No. 8 shade that’s popped up on everything from boots to watch straps in recent years. The change of pace from a roughout leather or a dark brown or black boot is refreshing, yet it’s not as distinctive as, say, a Dr. Martens Boot. These also look similar, in a way, to the much more expensive and revered Alden Indy Boots, another set of men’s boots worth buying.

That’s a very good thing — these look sporty thanks to the ridged Vibram Christy sole, yet I still found they paired comfortably with tan chinos and a striped henley for exploring around Manhattan. I did find (and I’ve found with other boots in this style), that the leather breaks in easier than other leathers — and because of the shine of this pair, it shows creases more easily (as you can see below). However, it’s nothing some well-timed leather care can’t fix, and it definitely doesn’t detract from their wearability.

Lining them up after a few weeks of wear. With some care and treatment, the Color No. 8 Diplomat Boot should hold up just fine.

Lining them up after a few weeks of wear. With some care and treatment, the Color No. 8 Diplomat Boot should hold up just fine.

That’s another area in which this pair of rugged leather boots excels — the versatility, erm, department. I’ve broken them out with a slim chambray shirt and a wool blazer, and I’ve rocked them with the aforementioned tan chinos, too. A trim pair of denim breaks just right on the bend of the boots, making for a pretty sleek look (something that can help everyone out). I could definitely see them working well with some wool trousers and perhaps a navy crewneck sweater on a more casual day at the office. The burgundy color would also pop nicely with some trim black denim (more on that later this week), and they’re going to fit right in with lightwash jeans in the spring, too. Seriously, the best leather boots for men can take you just about anywhere.

One of two other options in the brand's Diplomat silhouette, this one made out of Natural Horween leather.

One of two other options in the brand’s Diplomat silhouette, this one made out of Natural Horween leather.

The white ripple sole might cause some to shy away from these leather boots for men — after all, it’s different than what we’re normally accustomed to seeing in the way of boots. But that again makes it a nice style move. It’s not as if these boots are absurdly priced, so if you’ve been looking to try something different, this is but one way to go. The Diplomat line  also features a pair of Natural Horween leather boots with a Goodyear-welted sole, and a pair in Brown leather. So, the Color No. 8 pair is just one way to make an impression.

And yet, it’s the pair I’ve found myself gravitating toward the most. Thankfully, the other details work out as promised. The eyelets and laces have held up well trekking through the Brooklyn snow, although the lack of extreme traction could be a bit tricky in some instances. However, the Vibram sole is also as comfortable as advertised, even when worn for long periods of time. They run true to size, so there was no slippage (or cramping up of my feet, conversely) with some striped socks. Some have had issues with stitching imperfections or other problems around the sole, but there were no major problems with this pair — again, one reason why it’s worth it to pony up for a pair of these as opposed to something from, say, H&M.

They’re nice enough that if you were feeling adventurous, you could rock them with a slim grey flannel suit and a chambray dress shirt. Make sure you nail the break of those trousers and you’re all set. And that’s about all you can ask for from a sub-$250 pair of boots, especially ones made from Color No. 8 Horween Chromexcel leather. From chinos to jeans to wool trousers, they can do it all. Even on days besides Thursday (see what I did there?).

For more of my favorite boots, check out Taylor Stitch, shop the pages of Huckberry or find another pick for men’s leather boots here.

Have you tried out some boots from Thursday Boot Company yet? How would you style this pair?

Elevated Basics. Grounded Price.