Oak Street Bootmakers Review: Military Boot Showdown (Trench vs Field Boots)

Oak Street Bootmakers have a unique place in the scene: classic and understated good looks, an unusual degree of hand making, and an unusually low price — once you know what you’re looking at.

Founded in Chicago in 2009 by George Vlagos, Oak Street sources its leather from the world’s top tanneries, including America’s beloved Horween, and today you’re in for a double review of their two bestselling models that I’ve been wearing for years: the Trench boot and the Field Boot.

After more than five years with this brand I’m going to tell you about how they’re made, who they’re for, how they fit, why they cost more than some other American-made boots, and how they’ve changed since I bought my first pair. Because a lot of information online is out of date — including my old review!

Pros & Cons: Oak Street Bootmakers

Here’s a quick rundown of our Oak Street Boots review; these pros and cons apply to both of the very similar models that are getting the spotlight.

Pros

• Made in America
• Available in several well regarded leathers
• Hand lasted; a rare and artisanal touch
• Simple, versatile design
• Goodyear welted for resoleability and water resistance
• Price has been basically steady for ten years
• Roomy, comfy toebox that can accommodate E widths

Cons

• Sizing: they just go to size 13 and don’t do dedicated wide sizes
• Not all customers are willing to pay the premium for hand lasting
• The round toe might make them more casual than you’d want
• Some dislike the lack of speed hooks
• Some dislike the celastic heel and toe counters and would prefer leather

Why Trust Us

I’ve reviewed a ton of boots, doing the extra legwork to learn everything I can by traveling the world to meet bootmakers, designers, tanners, and other footwear experts. Seriously, I’ve been to over a dozen countries to learn the ins and outs of producing leather and footwear.

To prepare for this review, here’s a shocker: I wore the darn things for years and years. But I also interviewed the brand’s design director, George Vlagos, to learn the why behind some of the more interesting elements of these boots. I drew on several interviews I’ve had with various members of the Horween family about these leather choices and on discussions with shoemakers in Indonesia and India who employ some of the rarer techniques found at Oak Street Bootmakers.

The Company: Oak Street Bootmakers

Oak Street Bootmakers are one of the more prominent brands that insist on staying made in the USA — and made well in the USA. Their footwear tends to emphasize vanishing art forms in shoemaking like genuine hand sewn moccasin construction and hand lasting, which I’ll discuss later on.

But I’m also a giant fan of their design, which I’d summarize with the term no frills. While their two bestselling models I’m dissecting here are based on military boots, there’s nothing ostentatious or flamboyant about them, nor do they come off as too utilitarian or too dressy.

The brand regularly comes out with limited editions in rarer leathers, but they’re never anything crazy, like pink leather. Everything is that ideal balance of good looking and understated. They’re just simple, low profile, not too voluminous and not too tapered boots that match any casual or smart casual outfit.

What’s So Different About Oak Street Bootmakers’ Construction?

• All Oak Street Boots are hand lasted
• Boots spend one week on lasts to better take up their shape
• Bottomed without using industrial presses
• Handtack embellishment on the Field model

The main thing that sets Oak Street apart from other boots is that they’re made in the USA and emphasize old-fashioned and laborious methods.

Because the word “handmade” doesn’t mean much, we’ll go into more detail. The uppers are stitched by eye rather than machine and the bottoms and backstays are affixed by hand without the usual industrial presses, but the big difference with other USA-made boot brands like Red Wing is the fact that they’re hand lasted.

According to Vlagos, this makes for a better, more consistent fit between boots.

With hand lasting we can adjust the tension and shape the leather to how it wants to be shaped.

To back up just a bit: a “last” is a foot-shaped mold that determines the fit and shape of a shoe or boot. Usually, a shoemaker will stitch together the pieces of the upper flat on a table before it gets pulled over the three-dimensional last and then attached to the sole.

The vast majority of operations like Oak Street Bootmakers will use one or more machines to “last” the boot, stretching it more or less uniformly over the mold.

But high end shoemakers prefer to last by hand: each piece of leather — depending on where it comes from on the hide or how it’s tanned or what animal it’s from and so on — will stretch differently, in different places, in different directions, to different degrees, on different parts of a shoe, which all experience different kinds of wear.

The best way to last a boot while taking all of this into consideration is to do it by hand by a very experienced craftsperson who is able to deduce these properties in each piece of leather and each piece of the shoe when they’re handling it.

“When hand lasting, you feel the point where it has stretched as much as it should stretch,” says Vlagos. “So you’re getting a way better fit from a shoe that’s hand lasted.”

Once they’re lasted, the leather needs some time to better take up the shape of the last. Most brands speed this up by putting the boots in an oven or a room that’s akin to a sauna. Oak Street uses the old school method of just leaving the uppers on the last for at least a week: this is also meant to produce a better and more consistent fit — but it takes more time, and time is money.

Oak Street Bootmakers’ Leather Quality

• The Trench and Field boots are best known for their Chromexcel colorways
• Chromexcel is a good balance of tough, flexible, comfortable, and hardy.
• Oak Street regularly releases limited editions with cool leathers from around the world.

The specific boots I’m highlighting are made with each model’s most popular leather: the Trench boots are in natural (meaning undyed) Chromexcel and the Field boot is Chromexcel roughout: that means it’s the same leather but flipped inside out, so the fuzzy side is on the exterior.

Both boots come in an array of leathers, most of them Chromexcel, but Oak Street’s customer base just loves the natural kind more than any others and it’s become closely associated with these models and the brand.

Natural Chromexcel

Whether they’re $200 Thursday Boots or four-figure Japanese boots, every boot company worth its salt has at least one model in Chromexcel and it’s usually their bestseller. A combination tanned leather from Chicago’s Horween Leather Company, it’s just the best boot leather: tough but supple, easy for the shoemaker to work with, easy for the customer to wear, and it develops great patina as it ages — especially if it’s the “natural” Chromexcel that Oak Street’s known for.

Check out that picture above: when the undyed leather is new, it’s not too far off the color of skin. But as it’s worn in over the years, it darkens into the rich caramel you see on the right. It’s cool.

And it doesn’t take a lot of work to achieve — just put some Venetian Shoe Cream on these every 3 to 6 months. 

Chromexcel Roughout

You know how the inside of an unlined boot is fuzzy and suede-like and the outside is smooth? “Roughout” is the other way around. Why go with roughout? It’s basically scratch proof and needs basically no care. That’s why a form of Chromexcel roughout leather was the standard on World War 2 boondockers, the boot that inspired Oak Street’s Field boot.

No, roughout isn’t suede: suede is made when that full grain leather is split, while roughout keeps the outer grain of the leather and is typically thicker. Again, it’s regular leather flipped inside out.

Note that as I’ve worn them in, the outside of my Field boots’ heels have become smooth from wear and abrasion: you can expect your roughout boots to get a little less fuzzy in stress points as well.

But while you won’t get as dramatic a patina as you do with regular leather, roughout is way easier to care for. Many guys simply never condition them at all; if you really want to, though, you can use the spray version of Saphir’s Renovateur to give it a light coat in sweeping motions.

Otherwise, just dry brush it with a brass bristled brush when you feel they’re getting too dirty. If you want them looking as close to new as possible, follow the steps in our guide to cleaning suede. (I know I just said roughout isn’t suede, but for this intent and purpose, it is.)

Other Oak Street Leathers

You’ll regularly find limited edition boots on sale at Oak Street as well. Offerings have included the light and flexible Chieftain leather from Wisconsin’s Seidel, vegetable tanned leathers from Italy’s Badalassi Carlo, and even the occasional stag or moose leather.

I’m always impressed that Oak Street keeps releasing different limited editions — I missed a wild boar one they did a few years ago (and they swear they’re never bringing back), which I’m still bummed about, but that stuff keeps the brand exciting.

Sizing & Fit: Oak Street Bootmakers

• These boots have unusually round, roomy toes.
• Oak Street recommends you order true to size, not your usual boot size of half a size small.
• I’ve tried both 11 and 11.5, and wouldn’t have complained if I’d received 11s.

One of the absolute best things about both the Field and Trench boots — which are both made on the same last, so the fit is identical — is how extremely comfortable the bigger toe box really is. It was designed with an extra millimeter of space in the toe box so that your pinky toe can really breathe. 

I know, one millimeter doesn’t sound like much, but it really does make the difference between dying to come home and take the boots off and feeling like you can keep these boots on no matter how long or what your day entails. 

“The whole idea was to make a toe box where there’d be some extra room in the morning and then, as your foot swells and splays at the end of the day, they feel fine  — like they’re not being crushed,” says Vlagos. “It is very intentional.”

Unlike most boot manufacturers, Oak Street suggests ordering true to size, meaning your Field or Trench boots will probably be half a size larger than most of your other boots. My usual boot size is 11, and I’m in 11.5 with Oak Street.

They sent me some 11s as well so I could compare and honestly, I wouldn’t have complained if I’d been stuck with that smaller size — but I end up preferring the true-to-size model every time. It’s more comfy, and you’ve got room for thick socks if you need ’em. (I’ve also lent these boots to friends with feet a half size larger than mine, and they’ve loved them.)

The Downsides of Oak Street’s Sizing

Two problems: no wide sizes, and they only go as big as size 13.

There’s no solution for the big footed guys but if you’re wide? I think ordering true to size will be fine for an E-width foot and given how narrow the heel is, I think a EE dude could go up half a size and be perfectly fine. Maybe even a EEE dude could do that, but don’t quote me there.

Trench Boot vs Field Boot: Which Oak Street Boot Should You Get?

• The boots are honestly pretty similar; you can get them in the same leathers, and they have the same last. 
• The Field boot is more expensive, mostly because it has a more expensive sole and some extra finishing

Their two most popular boots are very similar: the same last, same sizes, same level of dressiness, same profile, same leathers, same hand lasted build.

The ostensible difference is the Trench boot is modeled after World War 1 service boots, the Field boot is modeled after World War 2 service boots. Neither are exact reproductions; they’re more like descendants.

In practice, here are the differences:

• The Field boot is more expensive: $518 versus $462 to $488 for Trench, depending on if you get the leather or Dainite rubber sole.
• The Trench boot’s a little taller.
• The Field boot’s heel appears sleeker because of its 270 degree Goodyear welt (this difference is only aesthetic).
• The Field boot’s nitrile cork sole is more expensive.
• The Field boot has some extra finishing, like a hand brushed welt and brass tacks hammered in the sole.
• The Trench boot comes with leather laces, the Field boot with flat waxed cotton laces.

Who Should Buy Oak Street Boots

• Anyone who enjoys a basic, uncomplicated, service boot aesthetic.
• People who enjoy a boot that can endure all kinds of weather and fits into smart casual environs.
• Anyone who has complained about their toes being crushed in boots with dressier toes.
• Guys who value the extra craftsmanship and made-in-USA ethos of the brand — because they’ll realize these are pretty well priced.

Who Shouldn’t Buy Oak Street Boots

• Guys who don’t care about the extra labor that prices these higher than Red Wing boots.
• People who prefer speed hooks.
• Guys with big feet; these sizes tap out at 13 for length and E for width.
• High end boot guys who prefer leather heel counters over celastic.
• Anyone who needs a super grippy sole for icier conditions.
• Folks who prefer a dressier, sleeker toe; for that you can check out their Lakeshore boot

I just have to highlight that I do think the elevated price is justified here. Consider the fact that the price of the Trench boot has increased something like 5% in the last ten years and we have just been through a period of extreme price hikes generally. For reference, inflation was 8% in 2022 alone in the U.S.

Personally, I think Oak Street’s boots just strike a great balance between being outdoorsy but also suitable for nicer outfits, and the construction is a nice compromise between standard industrial bootmaking and the ultra hand made, hand lasted, hand welted kind that are much harder to buy.

How Oak Street Boots Have Changed

• The Elston last was modified in 2018 to better secure the foot.
• Both boots are hand lasted only since 2020.
• Fiberglass shanks were replaced with steel shanks.
• They briefly swapped cork filling for foam during a pandemic shortage.
• Price has barely budged in ten years.

In my first review of these boots (after just a couple of weeks of wear) I echoed complaints I’d seen on reddit about the foot sliding forward a little as I walked.

That was because they used to have a leather sock liner in there that was too slippery. They’ve since taken that out and adjusted the last to remove the allowance of space for that liner, so they wound up adding about a millimeter to the toe depth and brought the toe spring down a bit.

It’s nice to see brands taking customer feedback seriously, and they definitely took care of the one major complaint we saw popping up from other users. They also heard a lot of customers say they preferred steel shanks to fiberglass, so that got swapped out as well.

There was also a brief period during the pandemic where they had to use foam instead of cork in the welt cavity. That’s long since been resolved and they’re now back to cork.

What Other Oak Street Boots Reviews Are Saying

We checked around the web but our first stop was the boot subreddit, r/Goodyearwelt.

People love the comfort and fit even before breaking them in: “Honestly, they’re the best fitting boot I’ve tried straight out of the box (narrowly beating my Viberg Country boots).” writes u/ravepool.

Dedicated boot reviewer 100wears would have preferred the extra water resistance of a storm welt but loves them overall, noting that “it can straddle the outdoorsy vibe while also being able to pull double duty as a slightly dressy option when pants cover the top.” He agrees with me about the last: “Being able to have a boot grip your foot without slip, while also letting your toes move is simply divine.”

As for the kinds of comments we’ve received on YouTube ourselves, folks tend to applaud a lack of break in and tend to complain about the lack of speed hooks, which is to be expected. It’s a gamble to leave them off a boot, even though I vastly prefer the extra security of eyelets. You can’t win this one.

Lastly, you’re going to see quite a few comparisons (and suggestions to buy) Red Wings for the price-conscious buyers who just can’t see the value or disagree that hand-made is necessarily better. If you want a cheaper option and speed hooks, you might be swayed (see more in the next section). 

Alternatives to Oak Street Bootmakers

Whether you like the look or you’re attracted to elements of the craftsmanship, there are other brands out there that might scratch your itch.

Thursday Boot Co’s Vanguard

Through a very boring mastery of supply chain logistics and direct to consumer digital marketing, Thursday Boot Co. has managed to produce this American-made service boot for under $300.

The differences are that it’s not hand lasted, the toe’s less round, and there’s a little less leather all around because of its slightly thinner upper and insole.

Grant Stone’s Diesel Boot

Grant Stone dominate the smart casual space with their range of Goodyear welted footwear made with world class leathers. The Diesel boot is the closest analogue to these Oak Street boots; the main differences are the more tapered toe and the fact they’re made in China.

That used to mean a gigantic price difference but nowadays, a Chromexcel Diesel is almost $450, so they aren’t that much cheaper than Oak Street. But they offer more widths and more leathers, so it might be what you’re after.

Red Wing’s Blacksmith

If you love Oak Street but prefer to spend under $350, Red Wing’s Blacksmith has a lot to offer: it’s also an American made, Goodyear welted, plain toe boot that’s pretty versatile.

The main differences? Blacksmiths aren’t hand lasted, they don’t have midsoles (so the shock absorption’s worse), and the toe has more volume, giving it a little more of a “work boot” vibe.

Unmarked’s Hunter

Unmarked stands out here for making boots that are hand lasted, are made with Chromexcel, and cost… well, about the same as Oak Street, even though they’re made in Mexico.

But the Hunter is made with stitchdown construction, which (in this instance) is more skillful, hardwearing, and waterproof. If that matters to you, you’ll know this is a good price for what you’re getting — and accept that custom orders can take up to 6 weeks.

Wrapping Up: Oak Street Bootmakers Review

Both the Field Boot and Trench Boot are dynamite boots that can be worn in environments both casual and smart casual.

Noteworthy highlights are they’re American made, decently priced, have a comfortably round toe, and the design is just the ideal balance of hard wearing and city friendly.

If you just don’t care about all the extra labor that goes into these relative to its competitors, then I’d understand you’re gunshy about the price. But I think I’ve done a solid job of illustrating that this brand is keeping the art of higher end American bootmaking alive and they’re doing it without gouging their customers.