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

#OOTD: How to Style a Crewneck Sweater This Winter

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.

So, welcome back to the #OOTD series here on The Style Guide. The above headline might seem a bit familiar — after all,  a slim crewneck sweater is a personal favorite of this blog, and it’s as well-suited for casual, rugged fall style as it is for layering in the early stages of winter. And the particular sweater that’s being featured today is as close to a perfect reinterpretation of a classic style as we’ve got — especially from lauded American menswear designer Todd Snyder. But what differentiates the below #menswear look from other features here on the blog? We’re throwing in more weather-ready layers, for one. And we’re mixing high-low style staples like a slim topcoat with everyday wardrobe staples. If you find you don’t have any of the picks below, it’s as good a time as any to get shopping. Got additional picks to add to the below list? Hit me up on Twitter, or check out the Instagram feed for a look into what makes The Style Guide (AKA, me) tick.

A high-low way to wear a crewneck sweater this winter. Not bad, ehh?

A high-low way to wear a crewneck sweater this winter. Not bad, ehh?

The Sweatshirt: Todd Snyder x Champion Pocket Sweatshirt, $98 — The Todd Snyder x Champion line is packed full of stellar, heritage and sportswear-inspired pieces. This Pocket Sweatshirt is exhibit A in  that regard — it’s comfortable, easy to layer and potentially your new favorite sweatshirt.

The Shirt: Life/After/Denim Windom Oxford Shirt, $128 — More than $100 for a classic Oxford shirt? Well, when it’s made from premium yarn-dyed cotton in a slim cut, it’s worth the investment.

The Topcoat: JackThreads Tieman Topcoat, $149 — So, here’s where a bit of that high-low style comes into play. The “topcoat-over-a-crewneck” look is something perfected by the likes of David Beckham, so I’d say it’s Style Guide-approved.

The Denim: Buck Mason Black Slim Stretch Denim, $175 — From the makers of your favorite short-sleeve chambray shirt comes a fantastic pair of slim black denim — just as ready for a  rock concert as a casual weekend coffee date. What belt to wear? Well, brown and black can work casually (keep reading), so reach for a braided leather belt.

The Socks: American Trench Fair Isle Sock in Merino/Cashmere, $28.98 — So, some of the picks in this particular #OOTD are quite pricey — including these socks. But American Trench does things as well as anyone when it comes to stylish, durable accessories.

The Boots: Thorogood Dodgeville Boots in Cognac ,$375 — Need another pair of durable, rugged leather boots in your closet? This handsome, versatile and easy-to-wear unlined pair of Thorogood Dodgeville Boots are a nice way to amp up the slightly more casual crewneck sweater.

The Watch: MVMT Watches Calypso Watch, $145 — From the stellar new Modern Sport Collection by MVMT Watches, the Calypso is a particular highlight. It’s got the handsome look of a rugged Tudor watch at a fraction of the price. Since it’s a casual outfit, a black rubber strap can work alongside the cognac Thorogood boots.

The Hat: Columbiaknit Marled Watch Cap, $17.98 — Sometimes, you don’t need to go too fancy with your winter accessories. In this case, the Columbiaknit Marled Watch Cap is neutral, simple and quite functional in the cold.

And, well, that’s all she wrote. When it comes time to layer up on a casual-but-cold day at the office or around town, you nearly can’t beat a stylish crewneck sweater — especially one made from premium materials. And pieces like slim black denim and a classic navy Oxford create a bit of a unique one-two punch, particularly when accented by an affordable (yet great-looking!) camel topcoat. When you top it all off with rugged, eye-catching cognac leather boots, it’s a mixture of pleasing colors and textures that work well when put together (yes, even the black denim and brown boots). Of course, you can’t go wrong with a warm winter hat or well-made Fair Isle socks. In fact, this head-to-toe look might just become one you break out time and again — at least, I hope so.

Stay stylish, and stay tuned for a (relatively) last-minute holiday gift guide coming tomorrow.

Thanks for reading!

-Beau

Style Pick of the Week: Original Chippewa Service Boots

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here.

Chippewa Original Service Boots

A rough-and-tumble pair of boots ready for winter style and exploration in equal parts.

Now, in recent weeks on The Style Guide, we’ve turned our attention to versatile essentials — like a stylish bomber jacket and a durable leather watch — but what about your winter footwear game? Seeing as we’re into December now, that’s where the Original Chippewa Service Boot is likely to come in mighty handy. Perhaps you’re dealing with the first — or second, or third — snowfall of the year and you want a durable, tough and rugged boot that’s still office-appropriate … once you kick off that snow at the door. Again, the Original Service Boot is a heck of a pair of footwear to pick up. It’s got a heartier construction and feel to it than something like the sleeker, dressier Astorflex Chelsea Boot — as seen on this blog earlier this fall — so this sturdy pair of Chippewa boots is going to stand up to all kinds of winter snow and slush. In fact, it’s a prime pick for casual, rugged style combos. And the best part about it? Unlike a more functionally inclined boot like the Danner Mountain Pass, this set of boots is still more than ready to pair up with  cold-weather business casual combos, too. How so? Think a wool blazer and a classic chambray shirt, plus slim dark denim on chilly days.  Oh, and the handsome Tan Renegade color is just an added bonus in terms of versatility. Yes indeed, if you consider yourself a fan of stylish winter boots, it’s yet another pair to consider adding to your #menswear rotation. Why exactly should you do that? Just as with lots of products sold via Huckberry, the difference is in the details — and then some.

Original Service Boots

In a rich, versatile Tan Renegade color, these leather boots represent serious everyday style.

Just like the full run of tough Original Chippewa boots sold through Huckberry, the Service Boot is 100 percent handcrafted in the U.S.A. That translates to a higher price point, yet also results in greater transparency, better quality and the type of style you’ve come to expect from the brand. The Goodyear welt on the Original Service Boot means they’re durable to begin with, but also come with the option be re-soled when you’ve put quite a few miles on them. The beautiful full-grain leather on the Service Boot will break in beautifully, too. Again, while you could always reach for a sleek pair of leather chukka boots or leather wingtips, those pairs aren’t going to stand up to the elements quite like the rugged-refined Original Chippewa Service Boot. The price point is definitely investment-worthy, don’t get me wrong. That’s why you should wear these boots confidently with everything from a waxed trucker jacket and burgundy corduroys to a slim crewneck sweater and olive chinos — seriously, try both of those combos for a bit of high-low weekend or weekday style.  With premium finishing touches like leather laces and nickel-finished eyelets, the Original Service Boot is a pair you can confidently wear on a bar crawl, to a rock concert or on a casual weekend coffee date — all in the same week. Get your pair of the Original Chippewa Service Boot while they’re around.

Shop the Original Chippewa Service Boot via Huckberry.

Have any questions on these boots? Better yet, want to recommend a Style Pick? Let’s connect on Twitter, y’all.

Online Shopping Picks: Best Men’s Winter Boots

Pick a boot, any boot. Back left corner: Wolverine 1000 Mile in Navy Suede. Back right corner: Timberland Britton Hill Waterproof Moc Toe. Center: Timberland West Haven Chukka. Front left: Thursday Boot Company Chocolate Suede Scout Chukka. Front right: Thursday Boot Company Roughout Captain Boot.

Pick a boot, any boot. Back left corner: Wolverine 1000 Mile in Navy Suede. Back right corner: Dr. Scholl’s Burke Boot. Center: Timberland West Haven Chukka. Front left: Thursday Boot Company Chocolate Suede Scout Chukka. Front right: Thursday Boot Company Roughout Captain Boot.

Welcome to our first Online Shopping Picks post of 2016! The extremely gradual change of the seasons this past fall & winter has left me a bit caught off-guard stylewise – as soon as the calendar hits late September and early October, I’m normally all about wearing sturdy denim, thick cardigans and tough boots whenever possible, on through December and January. But the fairly temperate climate in NYC made it somewhat difficult to do that when compared to previous years – I still have yet to see snow in NYC, an oddity for me considering cold winters growing up in Michigan. If you find yourself in the same situation, rest assured – winter will get here soon enough, likely with a vengeance. And when it does, make sure you’re prepared ahead of time with a standout pair of reliable winter boots. The picks that follow here were selected by yours truly for their combination of versatility, functionality and overall style. So you won’t find any steel-toed boots or extreme hiking boots below – just reasonably rugged, tough pairs that can work going into the office, going out after and maybe doing some light trekking off-road on the weekends. Check out these picks below, and let me know if I missed any!

#1. Jack Erwin Chester Captoe Boot — $220

A lovely shade of dark brown and a refined captoe merge with a hand-stitched rubber outsole.

A lovely shade of dark brown and a refined captoe merge with a hand-stitched rubber outsole.

The Chester Captoe Boot as seen here checks off three key boxes in rapid succession – great looks, a really solid price and that crucial rubber sole. Jack Erwin has been doing a great job releasing well-curated collections by the season (Exhibit A: its loafers), and its boots are no different. The captoe makes this pair sleek and office-ready like a dress shoe, particularly in the Espresso color, while the rubber sole can definitely get you where you need to go this winter. It’s likely the next step up pricewise from other picks, but well-worth it.

#2. Thursday Boot Company Brown President Boot — $199

No captoe, but still a relatively slim profile -- the President Boot from Thursday Boots.

No captoe, but still a relatively slim profile — the President Boot from Thursday Boots.

Whereas the Jack Erwin captoe is fully suit-ready, the Thursday Boots President Boot is a little more business-casual thanks to the slightly lighter brown leather and lack of a captoe. But that doesn’t make it any less sleek – it’s still got a slim toe shape, yet the rubber sole you’d expect from a durable winter boot. If the sole is anything like that on the Roughout Captain Boot or the Chocolate Suede Scout Chukka, it should provide great traction while holding up reasonably well. These can definitely be worn with a slim pair of denim and a navy blazer-chambray shirt combo as part of a daily uniform – throw in a sharp V-neck sweater if it gets cold.

#3. Wolverine 1000 Mile Boots in Navy Suede — $360

The Wolverine 1000 Mile Boot in Navy Suede, in person -- a Style Guide favorite.

The Wolverine 1000 Mile Boot in Navy Suede, in person — a Style Guide favorite.

The classic 1000 Mile silhouette gets a suede-centric upgrade – which also bumps up the price and knocks it a bit further down this list. However, these Navy Suede boots are true beauties – the suede feels smooth & rich, and the sturdy construction lives up to Wolverine’s standard. The profile is fairly slim as far as a boot goes, so these have looked right at home even alongside dark blue denim. I’d also recommend you try these out with light grey chinos, which should really make that navy suede pop. The price is going to be an investment that merits proper care, so they might be less ready to wear in all kinds of weather – but it’s going to be hard to leave them inside.

#4. Cole Haan + Todd Snyder Olmstead Boot in Chestnut — $249

Certainly more unique-looking, and perhaps more suited to casual wear, but still a durable and stylish option.

Certainly more unique-looking, and perhaps more suited to casual wear, but still a durable and stylish option.

The Olmstead Boot is marked down to $249 from its original price, so it’d be a wise bet to jump on them now (sizes are somewhat limited, too — from 8.5 up to 13, pushing it further down the list). They’re perhaps the most unique-looking pair of boots on this list owing in part to that wedge sole – they’ll likely wear a bit more like the sneaker-boots that seem to be all the rage. The moc toe silhouette and contrast stitching could make these a bit more tough to pull off, but the dark brown color grounds them a little bit. That should help them sit just right underneath slim grey or blue denim in a casual workplace. Pair these guys up with a navy crewneck sweater and slim tan chinos on the weekends, too – trust me.

#5. Red Wing Heritage Iron Ranger Boots in Black — $319.99

A sharp Black makes these a tad more refined than the thicker profile might suggest.

A sharp Black makes these a tad more refined than the thicker profile might suggest.

One of the most recognizable boot silhouettes in the game today, the Iron Ranger is another certified classic. It wears a little more bulky than the sleek Jack Erwin or Thursday pairs at the top of this list, and it’s pricier, so it does get knocked down the list. BUT, the black color makes this pair both rugged and fairly refined – they’re going to be that pair you reach for in extremely deep snow, yet could still leave on for work if you take care of them properly and match them up with the proper style essentials (like sturdy chinos or denim and a refined chambray shirt). Like the Wolverine boots above, these guys are a definite investment – but as investments go, it never hurts to stock up on tough boots before winter.
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So that brings us to the end of this list – know that some other budget options were considered, like the much-loved JC Penney Stafford Deacon Wingtip Boot. I’d also urge you to swing through the seemingly ever-expanding footwear offerings at J. Crew – they stock a variety of boots, including the classic Alden Indy, and sometimes offer them up on sale. It might seem as if there’s plenty of time before winter really hits – but it’ll be here before you know it. So stock up on your favorite boots, and wear them well this winter.

Tell me – what pair are you thinking about buying on this list? What’s your winter boot go-to right now?

Florsheim

Style Pick of the Week: Thursday Boot Company Chocolate Suede Scout Chukka

Editor’s note: Expect these posts weekly detailing one standout item coveted by yours truly. Sometimes, these fit within budgetary restrictions and other times, they’re expensive splurges worth saving for. For more Wish List items from Beau, head here, and to see other Style Picks, head here.

One option to style the versatile Chocolate Suede Scout Chukka from Thursday Boot Company. Slim denim by Mott & Bow. Baseball jacket by Grayers. Burgundy henley by Pistol Lake. VIntage ballcap by Goorin Brothers. Leather gloves by Iron & Resin.

One option to style the versatile Chocolate Suede Scout Chukka from Thursday Boot Company. Slim denim by Mott & Bow. Baseball jacket by Grayers. Burgundy henley by Pistol Lake. VIntage ballcap by Goorin Brothers. Leather gloves by Iron & Resin.

As my personal style has evolved over the years, my interest in footwear has grown, too. After all, learning more and more about clothes necessitates changing up how you dress for various occasions (from a job interview to heading to class and then work), and footwear goes hand-in-hand with that shift in perception. Now, I love my white sneakers for spring and summer, and I’m all about a sturdy pair of leather boots for fall and winter, but to me, there’s one type of shoe you can rock nearly year-round — the ever-reliable chukka boot. I’ve rocked the two-eye ankle boot style in some form for the better part of three or four years. Some are crafted from fine leather, some are crafted from suede; make no mistake about it though, the style fits in exceptionally well with everything from a polo and chinos in hot temps (ask James Bond) to a henley and dark denim in the chilly fall, as you can see here. And for the price, there might not be a better option than the Chocolate Suede Scout Chukka on the market right now from Thursday Boot Company. The brand has taken some flack from some online commenters out there (what footwear company hasn’t?) but my experiences have been nothing but great, and these chukka boots fit that bill as well.

Pair these boots with everything from slim denim to chinos (don't forget a pop of color in your sock game). Baseball jacket by Grayers. Stainless steel dive watch by Invicta. Slim denim by Mott & Bow.

A closer look at the pleasantly rich suede, which has  held up quite well for the price. Baseball jacket by Grayers. Stainless steel dive watch by Invicta. Slim denim by Mott & Bow.

Crafted with a  Goodyear welt construction that feels more sturdy than the price would suggest, the Chocolate Suede Scout Chukka in particular is an ideal piece of three or four-season footwear — think a tee and slim grey chinos in spring and a shawl cardigan and grey denim later in the year. And the dark chocolate color ensures they’ll do well in the transitional time of spring through the fall. Planning for lots of wear is even easier given that the suede is of great quality for the price — it’s smooth and sleek, and it’s held up well through a weekend exploring Washington, D.C. on foot. The full-glove leather lining is also quite soft, and one of the first things you notice about these boots is a slightly higher-cut ankle than your average chukka boot — that also extends the sleek feel and makes it easier to pair with slim denim. If you’re heavily invested in your footwear and used to paying substantially more than the purchase price of these chukkas, the Suede Scout might not satisfy you; if on the other hand though, you’re willing to pay a more-than-reasonable price for a versatile pair of chukka boots from a company on the rise, you’re in luck — Thursday Boots has you covered.

Editor’s note: Look for a full review of these boots in the weeks ahead.

Have you tested out any footwear from the brand? What’s your take on these chukkas and how would you style them?

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