Style Pick of the Week: Oak Street Bootmakers Dainite Sole Trench Boots

A durable pair of handsome brown leather boots made with Horween leather — not a bad pair to buy this winter.

Alright, folks — it’s another Style Pick of the Week, and we’re talking yet again about another stylish pair of rugged boots. Last week, it was the Rancourt & Co. Shearling-Lined Dresden Boots. And this week? It’s the Oak Street Bootmakers Dainite Sole Trench Boots, a heck of a pair of tough leather boots that just so happen to be exclusive to our pals at Huckberry.  And if you (or someone you love) still need a pair of winter boots? These might just be the ones to buy.  Based in Chicago, Oak Street Bootmakers provide standout quality and a classic approach to design and construction, helped along by beautiful Horween leather and the true Goodywear welt build on the Dainite Sole Trench Boots. The brand’s Elston last is surprisingly low-profile for a pair of leather boots, meaning you can more than easily wear these cuffed blue denim and  a classic shawl collar cardigan for style that’s at once sleek and slightly rugged. And the small details work out well for these stylish leather boots, too — the vamp has a calfskin lining for extra comfort and quality. So, if the specs are that good… that must mean the Oak Street Bootmakers Dainite Sole Trench Boots have plenty of styling potential, right? Right.

The studded Dainite sole adds some extreme traction and toughness.

For one, the silhouette means you can easily wear the Dainite Sole Trench Boots with outfits that reflect a little bit more tailored winter style. So, a navy herringbone blazer and charcoal plaid trousers work quite nicely with these boots. Yet, the Dainite Sole Trench Boots can still team up quite nicely with your more rugged winter essentials, including a casual grey crewneck sweater and broken-in blue denim. Add a tough waxed trucker jacket and call it a day. OK, well … don’t call it a day quite yet — get out there and get to work! At any rate, the Oak Street Bootmakers Dainite Sole Trench Boots are going to prove dependable time and again this winter season (and through the spring, too). They’ll only get better with age; Horween leather is built to break in quite nicely. Now, you’ll have to pay for your investment — the Dainite Sole Trench Boots will set you back more than $400. But, as your Style Guide author always says … that extra bit of coin is definitely worth it. Do you agree?

Are you going to be picking up the Dainite Sole Trench Boots for the winter weather that’s bearing down on us? 

See Now, Buy Now: Astorflex Is Making Your New Pair of Fall Chukka Boots

Astorflex

Sleek leather chukka boots crafted for durability and style all season.

We talk a lot about stylish leather boots here on The Style Guide. Specifically, we’ve talked a lot about rugged, stylish Astorflex footwear this fall season. The Astorflex brand can do it all, from classic suede chukka boots to Chelsea boots and lace-up boots, and they craft products with quality and sustainability in mind. And now, Astorflex  has definitely done it again — meet your new favorite pair of leather chukka boots. That’s certainly high praise, but stick with me for a second. The all-new, Huckberry-exclusive  Astorflex Greenflex Leather Chukka Boots are where it’s at this season — to put it simply.  You might already be familiar with the Astorflex Greenflex Chukka Boot in its original iteration — finished with stylish and sustainable suede. But the Greenflex Leather Chukka Boots from Astorflex up the ante considerably, starting with durable tan leather that’ll pair up nicely with fall favorites ranging from slim blue denim to grey corduroys or olive chinos. Yes, that’s right — they can work with #menswear combinations aplenty (including charcoal trousers like the Flint and Tinder 365 Pant as seen above).

That wearability starts with the premium construction of these stylish men’s boots, because you can’t rock leather chukka boots for days on end without a sturdy build. And the leather sole and stacked leather heel guarantee tough durability. Using soft European leather and the sort of handmade construction you can only find in northern Italy also guarantees great quality.  Yes indeed, the Astorflex Greenflex Leather Chukka Boots check all the boxes when it comes to a go-anywhere pair of durable leather boots. Feel free to wear these now with broken-in blue denim and a striped henley on the weekends, then keep them handy as you dress for fall travel or even a day at the office. The slim profile and handsome tan leather of the Astorflex Greenflex Leather Chukka Boots will team nicely with navy or light grey wool trousers and a navy blazer — plus an American-made Oxford — for meetings, presentations and drinks after work. Given all of those possibilities, how are you ever going to take the Astorflex Greenflex Leather Chukka Boots off? I’m not quite sure , to be honest.

Will the Astorflex Greenflex Leather Chukka Boots be joining your ever-growing footwear collection this fall? 

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.