Is This Reimagined WWI Army Boot the Perfect Fall Boot?

Billy Reid plus Oak Street Bootmakers equals flawless fall footwear?

billy reid x oak street boots on a cement floor

Published October 14, 2024

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What makes the perfect fall boot?

It has to be stylish — that’s a given. It should also straddle the line between a dress boot and a rugged work boot, making it suitable for practically any occasion. Bonus points if its looks are derived from American heritage designs that never go out of style.

Of course, it needs to be built to withstand the elements. Fall weather can be unpredictable, so some water resistance — especially on the sole — is an absolute necessity. Lastly, it needs to be built to last, with quality materials and, preferably, Goodyear welt construction.

Taking all of these variables into consideration, I think I may have found the perfect fall boot for 2024, courtesy of a new collab between Alabama designer Billy Reid and Chicago’s Oak Street Bootmakers.

Oak Street x Billy Reid Trench Boot

$548 at Billy Reid

In the Trenches

One of the signature offerings from Chicago-based Oak Street Bootmakers is the brand’s Trench Boot, an updated take on the U.S. Army M1917 Boot worn by American G.I.s in the First World War. Oak Street makes several versions of the Trench Boot in a plain or cap toe with a variety of Horween Chromexel leather uppers. All are made in the USA with Goodyear welt construction and feature either leather, Vibram mini-lug, or Dainite studded outsoles.

a pair of billy reid x oak street boots on a mans feet standing on leaves — Have I found the perfect fall boot?

Now, one of my favorite menswear designers, Billy Reid, has teamed up with Oak Street for a fresh take on the Trench Boot. Billy’s version isn’t a complete reinvention of the form. Instead, it adds a couple of signature tweaks to create what just may be the perfect fall boot.

Going Commando

The most prominent change Billy Reid makes to its version of Oak Street’s Trench Boot is the outsole. This version of the boot is equipped with a heavy-duty, English-made commando rubber sole. It features deep lugs and is thicker and more rugged than the outsoles you’ll find on other versions of the Trench Boot, yet it’s soft enough to provide comfort underfoot.

the rubber outsole of a billy reid x oak street boot — It’s not often you see Goodyear welt construction on such a rugged outsole.

The upper is also exclusive to Billy Reid’s version and uses full-grain roughout leather that’s undergone a wax treatment. This gives the boots an attractive weathered finish that will presumably improve with age like a waxed canvas jacket, along with a degree of improved water resistance.

I own several Billy Reid pieces, and one of my favorite things about picking up a new item from the brand is looking for the signature grosgrain ribbon logo, which is almost always incorporated in some subtle way somewhere in the design. On these boots, it’s particularly reserved, acting as the lining on the leather pulls. The standard Oak Street Trench Boot, by the way, has no pulls at all.

the leather upper of a billy reid x oak street boot — The waxed roughout leather upper is both gorgeous and practical.

Much of the rest of the boot is the same as you’ll find on other versions of Oak Street’s Trench Boot. It’s made in the USA and features Goodyear welt construction, a hand-lasted Barbour storm welt to keep water out, a calfskin vamp lining, and antique brass eyelets with speedhooks. The boots will last for years and years, as they can be resoled numerous times thanks to the Goodyear welt.

I’ve worn the boots a few times now and found them to be surprisingly comfortable out of the box. They’re a tiny bit stiff and will loosen over time, but I’m happy to report that mine didn’t require an extensive break-in period. They also seem plenty rugged, and while I haven’t put them through the wringer, the quality of the boots’ construction is evident.

the toe of a billy reid x oak street boot — The fine stitching on the soles clues you into the quality of these boots.

What I love most about these boots is their style. The stitching and Goodyear welt read “dress boot,” while the cut, commando sole, and roughout leather lean casual. The waxed roughout leather is especially gorgeous, and I can see myself wearing these with jeans, chinos, wool slacks — anything but the most formal pants will look great with them.

The bad news? Well, the boots are a limited edition, and a few sizes have already sold out. If you want to snag a pair of the Oak Street x Billy Reid Trench Boots, I recommend doing so sooner rather than later. You can get them at Billy Reid’s website for $548.