The Thursday Buy: Oak Street Bootmakers Delivers Some of the Best Men’s Boots to Lace Up Now

Is there a better time than right now to buy some of the best men’s boots for fall? Not quite, and that’s why it’s in your best interest to start carefully researching, shopping and, well, buying, because breezy, crisp seasonal weather is rolling through in earnest. And the boots in question at the moment are just what the doctor ordered this season, to say the very least. The Oak Street Bootmakers Trench Boots (an exclusive edition at Huckberry) blend everything you need in a standout pair of fall boots, from the classic silhouette to the rich, premium materials, making ’em some of the best men’s boots to shop this very instant. There’s no time to waste, after all, as we tick through the middle of October. Perhaps you’re looking forward to park strolls or outdoor beer garden visits, or even a return to the office. These stylish suede boots are everything you could want for all of those pursuits and then some (there’s a reason they’re exclusive to Huckberry — they’re some of the best boots, period).

The Oak Street Bootmakers Trench Boots are made with all the care and attention to detail one might expect from a product exclusive to Huckberry, and that’s great news for stylish shoppers (like yourself!) everywhere. For more than a decade, Oak Street Bootmakers has been making some of the finest boots and shoes right here in America, with heritage passed down through multiple generations (founder and current Design Director George Vlagos apprenticed alongside his father, an Illinois cobbler by way of Greece). It’s that family history and attention to craftsmanship that lends itself so nicely to some of the best boots for men, and the Oak Street Bootmakers Trench Boots live up to that legacy.

The difference really is in the details with the Oak Street Bootmakers Trench Boots, from the rugged brass eyelets to the use of durable, handsome-yet-rugged full-grain roughout leather from the Charles F. Stead tannery in England. This leather is going to get better with age, especially as you wear them consistently throughout the fall. The trench boot silhouette, as you can see above, is neither too bulky nor too slim, making these a pair of boots you can wear with jeans (dark blue or black should style up mighty nicely). And yet, the Oak Street Bootmakers Trench Boots are also wearable with olive chinos or burgundy corduroys, all owing to that rich, versatile shade of roughout Stone Waxy Mohawk roughout leather.

If it’s your new favorite boots you’ve been looking for, you just might have found ’em. They’re also made with Goodyear welt construction, meaning they can be resoled and quite literally revamped after years of wear. And here’s another thing about the Oak Street Bootmakers Trench Boots: You really will have them for years, which should help justify the higher price tag (they’ll run you $462 at Huckberry). It’s always worth it to have a pair of boots in your closet that you can count on, and the seriously dependable, highly stylish and effortlessly classic Oak Street Bootmakers Trench Boots are the ones to buy now.

SHOP: The Oak Street Bootmakers Trench Boots

See Now, Buy Now: Power Through Winter with the Natural Dainite Summit Boots from Oak Street Bootmakers

A surprisingly refined pair of hiking boots for the road ahead.

Let’s be clear here: Winter is still sticking around for a few more weeks — and likely longer — and there’s not much that any of us can do about it. One thing that can ease the pain of stomping through the snow again? Stocking up on men’s winter style essentials that’ll help you charge through the snow (or just stroll) while looking great. We’ve talked about Oak Street Bootmakers here on The Style Guide before, and the Natural Dainite Summit Boots are just as worthy of an addition to any lineup of rugged winter footwear you might have lying around. The Oak Street Bootmakers Natural Dainite Summit Boots play off the Chicago brand’s penchant for delivering beautifully made, versatile footwear — and the Dainite Summit Boots are that rare pair of hikers that are actually slightly … dressy, if you will? We’re not saying you can break these guys out with a navy flannel suit, but perhaps with some Donegal trousers and an American-made indigo overshirt? Certainly. And with the specs of the¬†Natural Dainite Summit Boots, you can be sure they’re up to the challenge in terms of battling winter weather.

Made from outstanding Natural Chromexcel Horween leather and featuring Goodyear welt construction — allowing ’em to be resoled after heavy wear — the Natural Dainite Summit Boots are sleek and rugged all at once, a rare find when it comes to dependable winter hiking boots. The UK-made Dainite offers superior traction on slippery surfaces, all without sacrificing looks — clunky winter boots, these are not. The calfskin lining on the¬†Natural Dainite Summit Boots is a comfortable, premium bonus, while the red laces nod toward outdoor heritage without detracting from the overall style of the¬†Natural Dainite Summit Boots — not a bad package overall, right? And I’d wager that the¬†Natural Dainite Summit Boots will only continue to get better with age; we’ve got plenty of winter left, so it’s imperative that you stock up — is it not?

If the Oak Street Bootmakers Natural Dainite Summit Boots end up in your closet, let me know! 

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?¬†

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?

Style Suggestion: Thanksgiving Dinner

At most times of year, and particularly Thanksgiving, it’s important to take time to celebrate with family and loved ones while enjoying some much-needed relaxation. Putting some thought into what you wear is just one way to make the occasion even more special. And you want to look good in those photos, right? Enjoy the week and Happy Thanksgiving!¬†

Thanksgiving oftentimes toes the line between between dressed-up and dressed-down, falling usually on one side of the spectrum. With some modifications, the outfit suggestion below should be able to fit in either way. The most important thing, though, is spending the day with those you love — if you’re able to dress well to do that, all the better! And for other Thanksgiving style ideas, see last year’s post.

Here’s the spread (See descriptions below for links):

Keeping things casual, yet crisp, for Turkey Day.

Keeping things casual, yet crisp, for Turkey Day. Cardigan: J. Crew Factory. Tie: JCF. Shirt & Pants: Bonobos. Watch: Invicta. Boots: JC Penney. Belt: H&M. Socks: Oak Street Bootmakers.

The Sweater: J. Crew Factory Shawl-Collar Cardigan 

This shawl collar cardigan provides more bulk and texture than a thinner cardigan (although a trim cotton cardigan could work if you go dressier). The marled grey color also fits in well with the shades of the season while not being too outrageously bright, unlike some sweaters on the market.  If the situation calls for getting more dressed up, navy corduroy blazer would work just fine.

The Shirt: Bonobos Hudson Brushed Blue Twill Shirt

The Bonobos option is a pretty substantial chunk of change for a regular, more casual buttondown shirt, but the twill fabric and diamond print add some nice texture and visual detail to the piece. Twill also adds some heft to stand up to that thicker cardigan. On the cheaper side, a dark denim shirt from J. Crew Factory provides that same visual bulk for a much lower price. And, a classic chambray shirt would also be a serviceable option.

The Tie (If Needed): J. Crew Factory Wool Herringbone Tie 

Some Thanksgiving dinners lean much more casual, and in that case, you could definitely ditch the tie. But should you want to reach for some neckwear, stick with a seasonal fabric with some depth to it ‚ÄĒ this brown herringbone piece changes up the typical charcoal wool tie you might see (Frank & Oak offered a standout option last year). It also blends nicely in terms of texture with that thicker cardigan and heavier shirt. Need a tie bar to keep it in place? Your go-to place is, of course, The Tie Bar.

The Pants: Bonobos Burnt Orange Washed Chinos (Or heavier pants in a fall-appropriate color)

Again, this is quite the expensive option for a simple pair of pants ‚ÄĒ but, on a personal note, these pants have gotten tons of mileage this fall, and that’s sure to hold true this upcoming winter as well. They don’t have the heft of a pair of corduroys, which one might typically go for at Thanksgiving, but like the rest of this outfit, these options are geared to go either dressier or more casual ‚ÄĒ washed chinos hit the middle perfectly. Many love Bonobos for their fit and great customer service, too. On the less expensive side, you could reach for a twill pant in a similar deep fall shade.

The Boots: JC Penney Stafford Gunner Men’s Leather Boots

Assuming that most of us will be in a colder clime for the holiday with the polar vortex that’s sweeping the nation, captoe boots¬†serve two functions: they combat the snow and also add a dash of style for sweeping through cold weather (see what I did there?). They aren’t the much-beloved brown Stafford wingtip, but black boots help to ground what’s already a pretty color-rich outfit. They also look a little slicker, helping bring a more dressed-up appeal to the ensemble. ¬†If you go really rugged-casual, some new boots from Frank & Oak could also meet the two criteria above.

The Rest: Invicta Men’s Pro Diver Watch, Oak Street Bootmakers Hickory Trail Sock, H&M Leather Belt

Since we want maximum versatility in an outfit, this Invicta watch, which calls to mind the Rolex Submariner,¬†is as classic ¬†and stylish an option as any. And although it’s not necessary, the black dial conveniently matches up with those boots. If you go more casual, a Timex Weekender with a simple canvas strap is always a safe bet, too. Since it’s going to be chilly out there, thicker socks that stay stylish thanks to their marled texture work very well with those black captoe boots above. Make sure your belt matches up with those boots, too.

What are your thoughts on the above picks? Anything you would change or add? What will you be wearing on the holiday?