Online Shopping Picks: The Best Men’s Boots to Buy This Fall

My friends, it’s that time of the season again — time to talk about the best men’s boots to buy for fall. The season is, as I’ve said in past weeks, perhaps the best for us #menswear fans — particularly if you’re a fan of rugged fall style essentials. We get to break out our favorite layers, from a slim denim trucker jacket to a rugged striped henley, and better yet … we get to break out stylish leather boots aplenty all along the way. A great pair of leather boots can complement nearly any outfit, and I think you’ll find that the picks below do just that. A herringbone blazer and slim dark denim? Throw on a pair of classic leather chukkas. A casual striped henley and grey selvedge denim? Stylish suede boots ought to do the trick. And that’s just the tip of the iceberg when it comes to the below picks.  Again, the right pair of leather boots  — affordably priced, well-made and supremely stylish — can take you from football tailgate to bar crawl and back, with a week of work in between, of course. So, start checking a few items off your men’s style wish list this season; I know I’ve got a few more picks to add to mine. Follow along on Instagram for real-time style updates, and let me know how we’re doing over at The Style Guide Facebook page.

#1. Original Chippewa 6-Inch Service Boot in Crazyhorse — $270
Original Chippewa

A not-too-bulky pair of rugged fall boots featuring durable construction and great looks.

Believe you me, it’s tough to play favorites when it comes to rugged leather boots for the fall season — but Original Chippewa just might take the cake when it comes to the  brand’s 6-Inch Service Boot. With a rugged silhouette that’s not too bulky — plus premium construction and a quality price — the 6-Inch Service Boot is darn near the whole package. Wear it with your favorite pairr of dark denim and a black moto jacket for edgy weekend fall style.

#2.  Hudson Shoes Elmore Boot in Black — $270

A sleeker, modern combat boot with plenty of style to burn.

Fancy something a little more sleek and less rugged? Hudson Shoes has what you’re looking for when it comes to the Elmore Boot. With the look of a classic combat boot, the Elmore Boot should lend itself well to rock n’roll-ready outfits — think slim, faded grey denim and a stylish graphic tee. The slick black color also lends itself to dressier pairings — if you’ve got a tan or grey herringbone suit in your rotation, the Hudson Shoes Elmore Boots are the boots with which to wear it.

#3.  Astorflex Bootflex in Dark Khaki — $190
Astorflex Bootflex

A rugged-yet-comfortable pair of lace-up boots.

Long a favorite around these parts for blending sustainability and great looks, Astorflex has been making — in recent months, anyways — what could just be your new favorite pair of boots — the Astorflex Bootflex in Dark Khaki.  Finished with a natural rubber sole for comfort and done up in a versatile shade of deep tan, the Astorflex Bootflex should work quite stylishly for plenty of casual fall outings — from the pumpkin patch to your next football tailgate.
#4. Red Wing Iron Ranger Boot in Harness — $300

As good as it gets — the legendary Iron Ranger Boot from Red Wing. Bravo, folks!

As legendary a pair of fall boots as it gets, Red Wing absolutely delivers the goods when it comes to its lauded Red Wing Iron Ranger Boot. Blame it on the Americana craze of the mid-aughts, but the Iron Ranger Boot has taken on a life of its own — and with good reason. It’s a ridiculously rugged, stylish and wearable boot that’ll break in beautifully over time. What’s not to love about that? A job well-done to Red Wing on this one.

#5.  Hudson Shoes Leiwston Chukka — $110

A sleek pair of chukka boots, made with versatile style in mind.

We’ll throw some classic leather chukka boots in the mix this time, just for fun (wink, wink). As first seen in our Style Pick of the Week series, the Hudson Shoes Lewiston Chukka blends a truly excellent price with quality craftsmanship and versatile style. These stylish leather chukka boots — this pair is an admittedly popular seller — can team with nearly anything in your wardrobe, from a worsted wool navy suit, a pair of slim grey denim or a faded pair of blue jeans.

Honorable Mention: Astorflex Greenflex Rough in Sand — $150

An updated take on the Astorflex Greenflex — the durable, treaded sole is a key point of differentiation.

As previously seen in this site’s See Now, Buy Now series, the Astorflex Greenflex Rough is a recent addition to the brand’s line of stylish and sustainably made boots (but you know all about those already). And the Greenflex Rough updates the classic suede chukka in a few crucial ways, starting with the durable sole featuring a treaded grip. It’s a neat tweak on a pair of boots that’ll work with broken-in denim, olive chinos or burgundy corduroys this season.

That wraps up our take on the season’s best boots, folks. What did you think? Any particular favorites on this list? Again, the versatility and rugged appeal of a pair of boots like the Astorflex Greenflex Rough can’t be emphasized enough — and a classic pair of tough leather boots like the Red Wing Iron Ranger certainly deserves its place on this list, too. Don’t forget the casual, versatile look of the Astorflex Bootflex, too — that’s one pair that you can put a lot of miles on this fall. And if it’s sleek fall style you prefer, the Hudson Shoes Elmore Boots are the ones to buy. Let me know in the comments below or on Twitter as to your favorite style — see you out there this fall!

-Beau

The List: Here’s All the New, Rugged Menswear to Rock This Fall

It’s time for another edition of The List, everyone’s favorite bimonthly roundup of, quite simply, the best men’s gear out there.  And today, we’re covering rugged gear for early fall — seeing as we’re nearing October, it seems fitting … right? By now, maybe you’ve stored away your classic summer sneakers and are reaching for heavier layers, pieces with some texture and heft to them. That’s all GREAT in the opinion of this #menswear writer — I can’t wait to break out even more fall style essentials across the weeks ahead. With that in mind, let’s check out this edition of The List — feel free to shoot me a note on Twitter with any questions, comments, feedback … you know the drill. Here we go!

Wolverine Original 1000 Mile Roughout Boot in Amber Suede — $299.98
Wolverine 1000 Mile Boots

An incredibly great-looking boot from Wolverine. Man!

My, oh my. Wolverine has done it again with a new take on the 1000 Mile Boot. The 1000 Mile Roughout Boot in Amber Suede looks absolutely gorgeous, well-made and rugged. Nice work by Wolverine back in Michigan, ehh?
Zodiac Super Sea Wolf 53 Compression Watch — $1,074.98

A truly expensive watch that truly backs up the price tag.

Have we jumped the shark  a bit by recommending a $1,000-plus watch? Well, Zodiac certainly knows its way around a timepiece — the Super Sea Wolf is durable, rugged and truly badass. Wear the Zodiac Super Sea Wolf with a rugged henley and classic leather boots, beer in hand.
Taylor Stitch Crewneck Pocket Tee — $58
Taylor Stitch

A classic pocket tee perfect for fall layering.

If it’s so close to fall, why are we recommending a stylish pocket tee as a top today? There’s never a bad time for a classic pocket tee, and the Taylor Stitch Crewneck Pocket Tee will work to layer handsomely under a rugged cardigan or a moleskin shirt.
Astorflex Greenflex Rough Boots — $134.98

A perfectly made, tough pair of classic chukka boots for early fall and beyond.

As previously discussed in our See Now, Buy Now series, Astorflex gets it right with the Greenflex Rough Boots. These classic men’s chukka boots featured an updated tread sole and the type of color & texture to pair well with plenty of other fall style essentials.

Sturdy Brothers Everyday Belt in Chestnut — $80
Sturdy Brothers

A handsome leather belt that’ll look even better the more you wear it this fall.

If you’ve got rugged leather chukka boots included in your outfit, you need a durable, classic leather belt that’ll fit right in with the heavier fabrics and textures of fall. Sturdy Brothers gets it right with the brand’s Everyday Belt.

Taylor Stitch Utility Shirt — $148

A uniquely textured, uniquely built shirt fit for fall layering.

More Taylor Stitch menswear in this edition of The List? Certainly. With a unique Army Green color, textured herringbone fabric and functional build, the Taylor Stitch Utility Shirt is practically made to be worn for weekend adventures — preferably layered over the Taylor Stitch Crewneck Pocket Tee.

Spiegelau IPA Glasses (Set of Four) — $32
Spiegelau

The best way to enjoy your favorite IPA — right? Right.

While we’ve talked to this point solely about rugged menswear for fall, the season is also an excellent time to break out a rich, finely crafted IPA on a cool night — ehh? The Spiegelau IPA Glasses are the perfect accessory for it.

Flint and Tinder Texas-Made Oxford in White — $89
Flint and Tinder

A well-made, well-fitting white Oxford shirt never goes out of style — agreed?

Another entry in our See Now, Buy Now series in past weeks, this American-made Oxford from Flint and Tinder is crisp, thoughtfully constructed and wearable with everything from dark denim to olive chinos and a grey cardigan.

DSTLD Slim Jeans in Light Wash — $95

DSTLD Jeans

Slim jeans in a light wash are a unique change of pace from your typical dark blue or black denim.

So, you’ve got your American-made Oxford  or your rugged Taylor Stitch Utility Shirt — what denim are you wearing?  With their cool light wash and slim fit, these DSTLD jeans are a unique change of pace from dark denim.

Ventus Black Kite B-01 Carbon Fiber Watch — $500

A sleek, strong watch that’ll work perfectly with plenty of fall style ensembles.

Want a tough, dependable and stylish men’s watch that pairs well with everything from an army green field coat and black denim to a herringbone blazer and black wingtip boots? The Venus Black Kite Carbon Fiber Watch is the one.

Outset Leather Grill Gloves — $20

Effective leather grilling gloves for all your outdoor cooking pursuits this fall.

Believe you me, fall is as good a time as any to fire up the grill at a tailgate or a bonfire — and these durable Outset Leather Grill Gloves are a go-to accessory.

Line of Trade Machined Steel Bottle Opener — $23.20

A sleek and tailgate-ready bottle opener — just add your favorite beer.

Just as badly as you need durable grilling gloves for your next tailgate, so too do you need a handy, durable bottle opener. Is it one of the best bottle openers to buy this season? Well, it’s durable and it doesn’t look half-bad, so … yes.
Titanium EDC Essentials — $89

A crisply designed everyday essential that’ll keep everything you need in one place.

The next time you head out on a weekend trip or a day hike, bring along this handy everyday carry essential — you might be surprised how often you find a use for the simply designed Titanium EDC Essentials.
Thursday Boots Grizzly Wheat President Boot — $199
Thursday Boots

Handsome, durable boots that’ll break in quite well over time this fall.

Last but not least — these rugged leather boots from Thursday Boots are the ideal complement to fall outfits aplenty — particularly if you layer up with something like the  Taylor Stitch Utility Shirt.

OK, Style Guide readers — that’ll do it today for this rendition of The List! What was your favorite? Personally, I love the  Taylor Stitch Utility Shirt. At any rate, thanks for reading — stay stylish!
-Beau

See Now, Buy Now: Pick Up the Taylor Stitch Maritime Shirt Jacket in Time for Fall

Your new favorite fall shirt? Your new favorite fall jacket? A little bit of both? Sure thing.

When a brand like Taylor Stitch consistently churns out excellent outerwear and men’s style essentials season after season, you start to sit up and take notice when cool products drop — that’s why we’re coming at you with another entry in our See Now, Buy Now series. And one of those attention-grabbing releases as of late? Well, my friends — that’d be the Taylor Stitch Maritime Shirt Jacket. You’ve seen it before as a layering option when it comes to how to wear a rugged overshirt this season — if you read this site on the regular, that is. Simply named, carefully constructed, durable and uniquely stylish, it’s certainly got the potential to be a favorite layering piece this season. and it’s surely one of the best men’s fall jackets — even if it’s technically part shirt, part jacket. What’s the secret that makes the Taylor Stitch Maritime Shirt Jacket such a winner? It’s definitely got plenty going for it. For one, this Taylor Stitch shirt jacket is am affordable steal when it comes to rugged fall layering.

A handsome sun-bleached indigo finish makes it ready to pair with dark blue or black denim alike, and the Taylor Stitch Maritime Shirt Jacket can also layer easily over other essential fall pieces (dare I say it — a Taylor Stitch striped henley). In short, it’s the perfect casual jacket for fall when it comes time to grab and go, whether your weekend takes you to a football tailgate, a day hike, a bar crawl or a bonfire. Taylor Stitch developed and crafted this bad boy from garment-washed indigo cotton in California — so if it can stand up to breezy, chilly San Francisco days on the water, it can stand up to your own fall pursuits. I’d recommend you wear the Maritime Shirt Jacket with everything from a rugged striped henley and your favorite pair of dark denim to a classic Oxford and tan chinos on a casual Friday. And when the time comes to head to the pub on the weekend? The Taylor Stitch Maritime Shirt Jacket is going to work quite nicely for understated, well-designed style. Who’s ready for that first chilly day of fall? I sure am — and you know Taylor Stitch will have you prepared.

Style Pick of the Week: Criquet Shirts Striped Player’s Shirt

A clean, classic polo with eye-catching stripes and a quality fit. That’s what Criquet Shirts does so well.

Now, I know we’ve been talking about rugged early fall style here on the blog for a few weeks now, but … well, what if it’s not quite cold enough to layer up yet in your neck of the woods? Or, what if you deal with the heat year-round and want a wardrobe refresh? That’s what today’s Style Pick of the Week dives into — the Criquet Shirts Striped Player’s Shirt is your answer to both questions above, to say the least.  It’s gotta be among the best men’s polo shirts, for a few good reasons. Here at The Style Guide, we love the all-American style and crisp design brought to the table by Criquet Shirts— and if you want to squeeze every last drop out of what’s left of the warm weather, a  stylish striped polo is certainly a great way to do that. Crucially, the Striped Player’s Shirt retains all the key style details that you appreciate from Criquet Shirts (see this entry in our Style Pick of the Week series for more).  So, we’re talking a substantial, crisp collar and organic cotton jersey fabric. Plus, the bright white base on the Striped Player’s Shirt is a nice nod to breezy style in warm weather. And the fit on the Striped Player’s Shirt? It’s classic through and through — not too slim, not too baggy. So, once you’ve added the Striped Player’s Shirt to your shopping cart … perhaps you’re wondering how to wear a polo shirt to maximize the last of the warm weather?

In short, I’d break out the Striped Player’s Shirt just as often as I could before chilly weather starts to roll in. It’s a stylish, classic complement to your favorite pair of tan chinos, ideally teamed up with classic white sneakers for a bit of preppy style. The good news is, the Criquet Shirts Striped Player’s Shirt works quite well with more rugged pieces. Trust me — with its sharp four-button placket, you can throw the Criquet Shirts Striped Player’s Shirt on underneath an indigo denim jacket, finished off with stylish leather high-top sneakers. That sort of outfit is great for grabbing a beer with buddies or kicking back at your favorite Sunday brunch spot. And if you want to dial in a  business casual look, the Striped Player’s Shirt can get the job done there, too. Simply add a classic navy blazer, grey chinos and perhaps leather loafers — that combo is going to work for the rest of the month. And if you live in a warm climate? You can take the Striped Player’s Shirt with you nearly everywhere — a patio dinner, a rooftop bar, the beach … seriously the Striped Player’s Shirt can go anywhere. Criquet Shirts has again done a standout job crafting a sharp, tailored polo that toes the line between dressy and casual — pick it up now and wear it as long as you can.

Are you a fan of the Striped Player’s Shirt from Criquet Shirts? How would you style this shirt in warm weather?

See Now, Buy Now: Throw On The Flint and Tinder Stretch Denim Trucker Jacket For Rugged Fall Style

The rugged good looks of a classic denim jacket, finished off with the stretch and comfort you need for all-day fall style.

There are certain items that instantly catch the eye of your Style Guide editor, writer and “creative director” — like the perfectly rugged Flint and Tinder Stretch Denim Trucker Jacket. Newly introduced by the folks at Huckberry, it’s yet another standout Flint and Tinder item you need to add to your fall wardrobe. Heck, that’s why we’re coming to you with a very rare Sunday See Now, Buy Now entry on the blog. Now, I know you’ve got other things on your Sunday to-do list, be it a stylish Sunday brunch, a day of yard work, a stroll through your favorite park or something in between. But simply put, the Flint and Tinder Stretch Denim Trucker Jacket delivers the goods. Without a doubt, this is a rugged denim jacket provides that elusive combination of comfort, versatility and style that’s so prized.

The Stretch Denim Trucker is made from mid-weight, inky blue cotton denim featuring two percent stretch for mobility. The jacket’s going to break in over time, making it a stylish complement to olive chinos and classic suede chukkas at this point in the season — and once you’ve worn the Stretch Denim Trucker throughout the fall, you can keep it handy to wear with burgundy corduroys and your favorite pair of leather boots in early winter (preferably layered under a classic field jacket or topcoat). In terms of hardware, the custom metal buttons feature an antique finish for classic style, while the Stretch Denim Trucker is also built with a longer, slimmer fit. If you’re feeling adventurous, you could even step out in a denim-on-denim look with Flint and Tinder’s All-American Washed Denim. Here’s the last word: The Flint and Tinder Stretch Denim Trucker Jacket is stylish and rugged enough to wear with a host of fall style essentials; heck, it’s even worth using a bit of your weekend downtime to pick this bad boy up right now.

Will you be adding the Flint and Tinder Stretch Denim Trucker Jacket to your fall wardrobe? How will you layer it?

Style Pick of the Week: Rancourt & Co. Carson Low Sneakers

A fall-ready sneaker that blends high-quality construction and striking looks.

If you’ve clicked through the pages of The Style Guide recently, then you surely recognize Rancourt & Co. — and particularly, perhaps you recognize the Rancourt & Co. Carson Low. It’s the perfect pair of sneakers to wear to transition into fall; I don’t know much, but I’d bet you’ll agree. First seen in our #OOTD post on how to wear an Oxford shirt this fall, these handsome, rugged sneakers nearly check all the boxes when it comes to classic fall footwear. That’s no joke. While it’s nice to step into tried-and-true staples like suede chukka boots or leather work boots when the weather gets chilly, durable leather sneakers can work just as well from early September to early November. It’s especially helpful that in the case of the Carson Low, the fine folks at Rancourt & Co. have applied the same approach that makes the brand’s other footwear so great (Exhibit A: The 4-Season Ranger Moc). The brand got into making USA-made sneakers back in 2015, and they’ve amped up their approach this time around.

That means the upper on the Rancourt & Co. Carson Low starts with exceptionally high-quality Horween leather, a claim not many pairs of sneakers can boast. The Vibram Strighton outsole is another point of durable differentiation (say that five times fast). That construction ensures grip, traction and a visually interesting contrast from the Horween leather upper on the Rancourt & Co. Carson Low. It’s that blend of quality and style that makes the Carson Low so appealing — and certainly, worthy of an investment this season.

Racnourt & Co.

Roll your jeans now with the Carson Low, and then keep these sneakers around once we get into fall.

So, with a pair of sneakers this well-made and stylish, it begs the question: How can’t the  Rancourt & Co. Carson Low work in a plethora of style situations? Classic dark denim and a slim grey crewneck sweater? Add these sneakers, plus a rugged leather watch. A slim herringbone blazer and grey corduroy trousers? The Rancourt & Co. Carson Low is a tremendous style move. A black denim jacket and grey jeans at a pub crawl? Sure thing, the Carson Low is up to the task. The rich brown leather, sturdy sole and handsome silhouette makes these sneakers timeless, versatile and durable. Finished off with leather laces, the Carson Low could just be your new favorite pair of sneakers this fall. Again, they’re an investment that’s worth it on the footwear front.

Will you be buying the Rancourt & Co. Carson Low  for the fall season? How would you style these stellar sneakers? Let me know in the comments or on Twitter

#OOTD: An Updated Way to Wear Your New Oxford Shirt

If there’s one shirting style that tends to come up time after time here at The Style Guide, it might be the classic Oxford shirt. From a made-in-America Oxford shirt to the handsome Line of Trade navy Oxford shirt you’re going to read about today, there’s not a garment that more consistently works in so many style situations for today’s modern man (that’d be you!). Hopefully, you’ve already got one of the best Oxford shirts for men in your close. And although we talked about how to wear an Oxford shirt for summer, we’re shaking it up a little bit today. The below #OOTD is one that harnesses the best of end-of-summer style and yet uses rugged accessories like a heritage-quality leather belt and a tough stainless steel dive watch to nod toward the fact that fall is slowly but surely approaching.  Are you ready? I’m getting there.

Truly, I think you’ll find that the classic Oxford shirt seen below can work in all kinds of scenarios, from a casual weekend coffee run to a farmer’s market trip to a day at the office. That’s what we’re going for here, at least. And the great thing about your new favorite Oxford shirt is that it’ll work with plenty of pieces you’ve already got in your closet, from American-made denim to tailored sweatpants and crisp leather sneakers for a very laidback Sunday brunch. What do you say? Shall we get after it? Chime in on the below in the comments or on Twitter once you’ve checked out the #OOTD below. Shop on!

Line of Trade

Take that navy Oxford and pair it with slim chinos and classic kicks to step into September (and beyond).

The Oxford Shirt: Line of Trade Navy Oxford, $70 – Let’s kick it off with a modern-fitting, garment-washed Oxford shirt in a slightly different deep navy color. Ready to wear with anything — slim chinos included.

The Chinos: Banana Republic Aiden Slim Rapid Movement Chino, $98 — A recent addition to the BR line, these stretch chinos combine a tailored fit with a range of color options — although the shade seen here is perhaps most versatile.

The Sneakers:  Rancourt and Co. Carson Low in Natural Canvas, $175 — Made in America to exacting standards, these Rancourt and Co. sneakers are a more durable answer to classic white canvas sneakers — and all the better for it.

The Socks: Arvin Goods No-show Socks, $30 (Three-pack) — Because it’s not quite fall yet, we’re still rolling up our chinos to show off those USA-made sneakers — and Arvin Goods no-show socks are critical in that regard.

The Belt: Sturdy Brothers Everyday Belt in Chestnut, $80 — Tired of buying cheap accessories? This handsome, extremely well-made Sturdy Brothers belt is the upgrade you need for fall.

The Watch:  Timex Stainless Steel Waterbury Watch, $119 — Told you we’d be breaking out durable everyday accessories, right? This rugged stainless steel dive watch from Timex is a steal in terms of price and looks.

The Sunglasses: Classic Specs Lowerree Aviators, $88 — Perhaps you’re not familiar with Classic Specs  — I know I wasn’t — but pieces like these stylish Aviator sunglasses should change that in a hurry.

The Everyday Carry: Nisolo Lori Leather Tote, $134.98 — Wary of carrying a rugged leather tote when you normally haul around a stylish messenger bag? This handsome leather tote bag  is a new way to switch up your everyday carry.

Alright, then. Have a better idea of how to wear your new favorite Oxford shirt? When you start with a piece as classic and simply constructed as the Line of Trade navy Oxford shirt shown above, the possibilities are nearly endless. However, your Style Guide author thinks that keeping things straightforward is the best way to go. That is to say, slim chinos and natural canvas sneakers from Rancourt and Co. are standout building blocks for any outfit.  Add in fall-ready accessories like a rugged stainless steel dive watch from Timex  and a durable leather belt from Sturdy Brothers, and you’re set for this #OOTD — and plenty more outfits in the season ahead.  No outfit — especially one featuring a classic navy Oxford shirt — is complete without finishing touches like stylish Aviator sunglasses and a handsome leather tote bag, though. So, just as with many of your other favorite #menswear pieces, the little details matter, and starting things off with easily wearable essentials is the best way to say goodbye to one season and look toward the next.

Hope you enjoyed today’s post — and thanks for reading!

-Beau

Windy City Style: A Summer Weekend in Chicago

Checking out The Bean and Millenium Park on an outstanding summer day in the city. Wearing an American Giant tee and my Need Supply Co. denim jacket, with hair styling courtesy of AXE. Shot by Olivia Hayhoe on an iPhone 7 Plus.

Now, I know what you’re thinking. Wasn’t I just in Chicago? This month even? Yes indeed, Style Guide readers, my travels took me to Chicago for Lollapalooza 2017 just a few short weeks ago and yet … I’m back! Or at least, I was back this past weekend for a family weekend in the Windy City.  My last trip to the city involved a healthy dose of excellent music — including a terrific live show by The Killers — and I was just as excited to be back this time. Incredibly, I’ve even got a fall trip back to Chicago planned, whereby I’ll be sure to pack plenty of fall menswear essentials. Yet, these past few days were about reconnecting with family, exploring the city and catching up with friends right before the end of summer … all in style, of course!

The rest of my family made the trek to take in Chicago’s version of the famed American musical “Hamilton” … while I gave up my seat to my young nephew (Hi, Charlie!), leaving me more time to get out and about in Chicago. That entailed a post-dinner trek to famed indie venue Metro Chicago to see a great indie pop show by Ernest Greene (known by his stage moniker Washed Out).  I’ve gotten quite practiced at loading up my stylish weekender bag with gear to take on the season, from versatile outerwear to a slim chambray shirt and classic sneakers, and this weekend proved no different. Just remember: Going from city to city still calls for on-point travel style. So, let’s get to it.

Men's travel style

Breezy essentials for summer travel, starting with my Grayers Montreaux Windbreaker and carrying through to stylish Frank and Oak leather sneakers and my reliable Huckberry Explorer’s Cap.

Heading straight to the airport in the morning on Friday called for versatile, easygoing style — just as with my last trip to Chicago. Starting with a solid base layer is always key (especially when dealing with airport A/C), so my Grayers Montreaux Windbreaker, a classically designed jacket you might recognize from my Style Pick of the Week series, was the way to go. With its light weight and easy-to-style design, the Montreaux Windbreaker teamed nicely with my equally laidback-yet-polished Mott and Bow denim shirt. Perhaps you recognize the new line of Mott and Bow denim shirts from this site’s Style Pick of the Week series, and I’d say any of the brand’s denim shirts would be a versatile bet the next time you need to throw on a crisp, casual top for travel.  The soft fabric and nicely tailored-but-mobile fit of this slim denim shirt made it an ideal airport layering move, while a new pair of Banana Republic Rapid Movement Chinos offered just the right blend of comfort and stretch.

The whole combo was topped off with my trusty-as-ever Huckberry Explorer’s Cap, a pleasingly vintage-inspired ballcap I love to throw on any time I need to keep the sun off my face.  On the footwear front, a pair of Idyllwild Pull-Up Leather Sneakers from favorite menswear retailer Frank and Oak helped me move around the city with sharp looks and wearbility in mind. And to stay on time, I threw on my trusty Timex x Red Wing Waterbury Chrono, a standout piece from the Timex Waterbury line that looks rugged and goes just about anywhere (particularly with a classic windbreaker and a stylish denim shirt). Want a winning formula for travel style? Pair mobile stretch chinos with leather sneakers and a comfortable shirt featuring textured fabric. 

It’s a good thing I was prepped with versatile menswear, because Friday packed in a heck of a lot of exploration and great times around the Windy City. Our accomodations at TheWit Chicago were outstanding — right in the the heart of downtown Chicago, this modern hotel provided a sleek backdrop and stellar views from its roof bar (the ideal spot to knock back a few Bell’s beers — good to be back in the Midwest!). And Friday night’s dinner, featuring family-style pizza, cheese plates and plenty of bread and olive oil, was nothing less than excellent. The next time you get to Chicago, I’d recommend you stop by Quartino!

Mixing earthy tones and casual, versatile staples like an American Giant pima tee and Banana Republic’s Rapid Movement Chinos alongside the CLAE Bradley Mid.

And with Friday in the books, Saturday dawned with the promise of an exciting full day getting to know Chicago more. Seeing as Lollapalooza was packed wall-to-wall with music and I hadn’t visited since college, that left plenty to do — including lots of time spent strolling through MilleniuM Park. As per usual, I prepped with the best men’s gear that I could possibly muster, including a mix of high-low, casual style led by a crisp charcoal pair of my Banana Republic Rapid Movement Chinos. Seriously, if there’s a pair of chinos that combines better range of movement or a more crisp look — the tab closure waist helps with that — I’ve yet to find ’em.  My charcoal chinos matched up nicely with a well-made, breathable Amerian Giant Premium Crew Tee in Drab Olive — a nice contrast of earthy tones that worked well to go from Millenium Park to cool spots like Raised, an urban rooftop spot outfitted with industrial fixtures, premium cocktails and local craft beer.

Saturday’s full ensemble for exploring Millenium Park, highlighted by my CLAE Bradley Mid Sneakers, plus my trusty Need Supply Co. denim jacket and the TImex x Todd Snyder Military Watch.

Like other American-made menswear that I favor, I think you’ll find a simple, stylish T-shirt works with anything on vacation.  The key to a versatile look came from my  Need Supply Co. Denim Jacket in 96, another piece that proved a favorite at Lollapalooza 2017   — it worked just as well this time around, especially as a shot of color to contrast my rich Cocoa Leather Bradley Mid Sneakers from CLAE. This style is comfortable and durable, and for this late August trip, that made them a prime footwear pick. That comfort definitely helped me get around in style — my MVMT Watches Runaway Aviators also helped shield my eyes from the hot Chicago sun, and we took the chance to keep the afternoon rolling. The Chicago Athletic Association Hotel, completely refurbished and recently reopened, harkens back to the city’s glamour and refinement of years gone by. It comes complete with a rotating pop-up bar on the ground floor, plus a game room and  a neat rooftop bar with great lakefront views.

A stylish weekender bag, American Giant shorts and a breezy chambray shirt made for easy travel style.

But as always seems to be the case, the weekend drew to a close too quickly. I had just enough time for a delicious Sunday brunch at the uniquely ’70s-inspied HopCat Chicago lounge before departing the Windy City yet again — and I dressed in casual, breezy travel style to take on the day. For a bit of tailored style mixed with supreme comfort, my all-new American Giant Weekend Shorts — made from hefty rugby jersey cotton — were perfect for a flight back to NYC. And to mix in some high-low style, I threw on my trusty United By Blue Wenlock Chambray Shirt. What with breathable fabric and a neat pattern, the Wenlock Chambray Shirt added some contrast to my laidback CLAE Hayward Sneakers, at once retro and yet crisply modern. And on the accessories front, a handy travel kit and men’s grooming essentials from Baxter of California paired up perfectly together, while my rugged-yet-accessible Timex Waterbury Chrono Diver helped me stay on time in casual style. In all, the laidback, breezy style ensemble helped me make it back to NYC in good time and in good style.

I hope you spent your weekend in the same way I did — with great friends and family, enjoying great times. You can  be sure I’m already looking forward to my next trip — to Chicago or elsewhere. To keep up with my travels and my style tips, check out my Instagram. And tomorrow, you can join us for another #OOTD. Until then, stay stylish!

-Beau

The Friday Read: Essential Everyday Carry Gear, Craft Beer and Nisolo Shoes

Can you believe another week is in the books? Heck, can you believe I’m in Chicago again for the second time this month? I certainly can’t — and yet, today’s edition of the Friday Read is coming to you live from the Windy City. I trekked to Chicago just a few short weeks ago for Lollapalooza 2017, and had a great weekend dressed in ideal music festival style. This time around, I’m meeting my family back in the Midwest for a weekend of city exploration and crucially, a family trip to see lauded American musical “Hamilton.” Having seen the show twice already, I gave up my ticket to my young nephew, a budding musical enthusiast and huge fan of the standout musical. So, that’ll free up some time for me to explore all that Chicago has to offer — anywhere that’s a must-see on your list? I’m looking forward to hitting up the Chicago Athletic Association Hotel, a refined, old-school art-deco spot with (apparently) a neat speakeasy. That’s just one of many stops I’ll be making, though. Follow along with all the action on Instagram, and be sure to check back here for a full #menswear trip recap on Monday. Until then — stay stylish and enjoy the below weekend reading picks!

  • Fall is a great time to hit the road for day or weekend trips — heading to a winery, a brewery, an orchard … you name it, and it should definitely involve essential travel style. To that end, I rounded up the best everyday carry gear for your next drive. Head to GearMoose to check it out.
  • We enjoy talking craft beer around these parts — to say the least. With that in mind, I point you toward The Manual — my colleague Lee Heidel is taking you into a new initiative from the Brewers Association to properly label beer from breweries that fit the definition of “craft.” It’s a worthy cause that might just make you love your favorite beer even more — agreed?

  • Let’s stick with the latest happenings at The Manual — shall we? Namely, I rounded up my favorite picks from Nisolo, the ethically crafted footwear makers behind a whole host of stylish chukka boots, rugged sneakers and plenty more. Shop away!

OK, everyone — we’re keeping it short this week! Enjoy the weekend, and check back for tomorrow’s Style Pick of the Week.

Thanks for reading!

-Beau

See Now, Buy Now: Add to Your Watch Collection with the Timex Waterbury Stainless Steel Dive Watch

Timex Waterbury

One heck of a watch for the price — maybe one to buy right now, as it were?

One of the things that comes up a lot at The Style Guide (weekly? daily?) is the importance of buying quality, affordable and versatile #menswear pieces. From a classic Oxford shirt to a rugged henley to slim, American-made denim, that type of quality and wearability is out there — if only you know where to look. Such is the case with Timex, a brand that you might have glazed over in the past, one that now deserves a second, or third, look. And in the latest entry in our ongoing See Now, Buy Now series, we’re giving the rugged, essential Timex Waterbury Stainless Steel Dive Watch a close look — it’s among the best men’s casual watches to buy now, I can say that much.  The Waterbury Stainless Steel Diver plays off the brand’s vintage-leaning, stylish Waterbury line — surely, you’ll recognize the rugged Timex x Red Wing Waterbury Chrono from the pages of this blog. The Waterbury Stainless Steel Diver is in a league of its own, starting with the standout price and carrying right on through to its handsome, subtly stylish and easily wearable aesthetic.

It’s a rugged men’s dive watch that gets the look right without a cluttered design. While it’s not exactly made for plunging into great depths in the ocean, it’s a daily watch that’s more than serviceable thanks to the classic durability for which Timex is known. For you and me both, that’s great news. And the better news? You can get it via Bespoke Post, purveyors of plenty more of your favorite #menswear.  If there’s one watch to wear to the office with a classic navy blazer during the week while also teaming it with a rugged short-sleeve henley on the weekend, it’s the Waterbury Stainless Steel Diver. Folks, that type of affordable style can’t be emphasized enough. And a rugged stainless steel dive watch is the perfect piece to add a bit of toughness and visual interest to cold-weather outfits, too — perfect given that we’ll be into fall before you know it. With all that being said … I can’t recommend the Waterbury Stainless Steel Diver enough. That’s as true right now as it’ll be when fall hits.

Shop away, and thanks for reading!

-Beau