Oak Street Bootmakers Trench Boot Review: Handcrafted in America Boots

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by  William Barton | Last Updated: 

Oak Street Bootmakers are a lesser-known brand, but some people absolutely swear by them. But when you’re looking to spend this kind of money on a boot, it helps to know everything you can before following through.

In this Oak Street Bootmakers Trench Boot review, I’m going to break down all the facts and show you a few things I wish I knew about the Trench before I bought mine.

Review Feature Image/Icon Image source: Oak Street Bootmakers

Oak Street Bootmakers Trench

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Bottom line: The Oak Street Bootmakers Trench Boot has a simple look but packs a punch in terms of quality and durability. They have a wider, flatter toe than many other plain toe boots I’ve tried, and they’re a bit pricey compared to similar-quality brands like Grant Stone, but they’re entirely made in the USA, almost exclusively of USA materials.

Ratings:

At a Glance Feature Image/Icon  Design At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon
At a Glance Feature Image/Icon  Quality of Materials At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon
At a Glance Feature Image/Icon  Craftsmanship At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon
At a Glance Feature Image/Icon  Fit & Sizing At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon
At a Glance Feature Image/Icon  Value for Money At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon At a Glance Feature Image/Icon

Pros:

  • The Trench is available in several varieties of Horween Chromexcel leather (mine are in Natural Roughout)
  • Construction quality is impeccable
  • They’re made in the USA and most of the materials are made domestically as well

Cons:

  • I’m a speedhook man, so I’d love to add some on the Trench

Oak Street Bootmakers most popular boot is a take on a classic: the m1918 Pershing boot used in the cold mud of WWI European trench warfare. 

I figured I face a lot of similar conditions when walking my shih-tzu around the neighborhood, or trying to find a self-starting fire log at Ralphs, so I decided to give the Oak Street Trench a try.

I’ve put these Trench boots through some tough treatment (literally day one, I fully submerged them in a river), and I’m going to share a few things I wish I knew before buying them. 

Oak Street Trench Overview

oak street trench boot flatlay top down

The Oak Street Bootmakers Trench Boot is an homage to the hard-wearing boots made by US manufacturers for American, French, and Belgian soldiers fighting in the trenches in World War I.

While those original trench boots had hobnails (basically metal spikes to help keep your footing in the mud), the Oak Street Trench is designed for more casual wear. 

One thing I appreciate about Oak Street is that they’re entirely made in the USA, and they pride themselves on sourcing just about everything they can from the states (including their shanks, eyelets, and laces). 

The only notable exception to this is the Dainite Sole, which is British and also known for its exceptional quality.  

Oak Street Trench Boot
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Things to Consider Before Buying the Trench Boot from Oak Street Bootmakers

oak street trench boot in horween chromexcel roughout after patina

Before you buy the Oak Street Trench, take a look at the toe-box to see if it’s something you’re interested in. 

As you might be able to tell, the toe is wider at the front than many other plain toe boots. Personally, I enjoy the style, especially because I decided early on that these would be my beat-up boots. They’re tough, and I’m excited to see how the roughout patinas. 

Also, because the toe is wider, you may want to get a half size larger than you normally do for your other heritage boots: the Elston last fits basically like an E width because of the room in the toe. I’ll discuss more on this in the Fit & Sizing section. 

Model wearing the oak street trench boot on stairs

Lastly, it’s important to note that Oak Street Bootmakers boots cost a bit more than other similar-quality brands. To me, Oak Street’s quality is on par with Grant Stone. Both brands never miss a stitch, and use the best quality materials inside and out. Oak Street is roughly $70 more expensive than Grant Stone because their boots are made in the USA (Chicago, to be specific). 

It’s up to you to decide whether that domestic craftsmanship is worthwhile: again, there’s no quality difference from what I can tell, but knowing you’re supporting a USA-made brand may be worth the extra cost to you. 

Oak Street Bootmakers Trench Boot Review

First Impression

oak street trench in a field

These look like old-school battle boots, which is almost entirely the reason I wanted them. I needed a boot I could take with me camping, hiking, and still wear casually with my new raw denim jeans

I love the side profile of the Trench Boot: it’s simple and classic. The most popular Trench is the Natural Horween Chromexcel, but I opted for the Natural Horween Roughout—I’m a big fan of how roughout ages, and considering that I’m planning to run these through the muck, I’m curious what battle-scars they’ll pick up. 

I wasn’t expecting the toe to be as wide as it is, as that’s not something I think is well-communicated through the Oak Street site. Here, take a look at the Oak Street Trench compared to some other plain-toe boots. 

plain toe boot toe cap comparison

Hopefully that gives you an idea of how wide and flat the toe is. It’s not like they’re duck-bills or anything like that (I have a pair of Jim Green’s that are so wide and flat in the toe, they’re basically unwearable in my opinion), but they’re not slim and sleek like the Thursday President or anything like that. 

Leather Quality and Care

oak street trench horween roughout chromexcel new

Horween Chromexcel is renowned for its supple texture and durability. The most popular Trench Boot uses Natural Chromexcel, but I decided to get the Roughout Natural because I haven’t seen it elsewhere. 

I have plenty of Horween Chromexcel boots (and I’d be willing to bet you have a pair yourself—if you’re looking into Oak Street, you must know your stuff!). I love the leather—for fancier boots, I like the subtle shine you get. For everyday boots, I appreciate how well it ages and the weather resistance you get with it. 

For rugged boots, I love that it almost looks better when you don’t condition it.

oak street horween roughout leather after use

I have watch straps and laptop carrying cases made with the stuff. It’s fantastic. 

Oak Street uses a 2mm Chromexcel, so it’s decently thick and sturdy without being too thick to the point where it feels punishing. 

Because I got the roughout leather, mine are unlined (they don’t need a lining because the smooth side of the leather is already facing toward my foot), but the standard Horween Chromexcel leathers have a calf-skin lining. 

As for care, Chromexcel is easy to clean and condition. I really like Venetian leather balm for regular care, or if you want a little shine, Saphir Renovateur.

I’ve tested maybe 15 different leather conditioners out and those are two of my favorites. You can watch me compare the 10 most popular leather conditioners here:

For the roughout, I’ve conditioned them once by brushing them off with a suede brush and then spraying Saphir Renovateur (in a can!) on them. I’ll probably condition the roughout maybe once a year, possibly even less. It’s really tough and I actually want them to look a little beat up. 

Saphir Renovateur Suede Conditioning Spray
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Sole

oak street trench with dainite sole

The Oak Street Trench comes outfitted with a Dainite rubber studded sole. There used to be a time when the Trench had a leather sole, but Oak Street discontinued that, which I think was likely a wise choice—rubber soles make more sense on a boot like this. 

Dainite rubber has a nice balance between firmness for durability, and softness for traction and comfort. The first time I wore my Oak Streets, I actually ended up walking through a river for about a half-mile or so when visiting Big Sur. 

oak street trench dainite sole in water

I was bouldering over wet rocks and algae-covered slides, and the sole did extremely well keeping me upright. 

oak street trench dainite sole when walking

The Trench features a 360-degree Goodyear welt and uses a Barbour welt from Massachusetts (known as the best quality welt you can get). This makes the Trench boot very weather resistant, though if you completely submerge your feet in waist-high water for 30 minutes, well, your socks will get wet. 

In all seriousness, the Oak Street Trench does great with poor weather—when you combine the Goodyear welt with Horween Chromexcel leather and a Dainite sole, you have plenty of protection from rain and you likely won’t slip. 

Oak Street Trench Boot
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Fit and Sizing

oak street trench on model

Oak Street recommends to order your true Brannock size, which is unlike many other boot brands like Red Wing, Wolverine, or Thursday. The brand says to get whatever you normally would for your dress shoes or sneakers. 

I apparently disregarded that (I don’t think I saw it), and I ordered a size 10. I’m a 10.5D Brannock and normally get 10.5 in sneakers and dress shoes. Still, I don’t find my 10D Oak Street’s to be too tight.

I think the reason they don’t feel tight is because Elston last is so wide in the toe that you can get something a little more snug in the heel and still have room for your toes to spread out.

This is a bit of conjecture, but I’d say the 10D fits more like a true 10E, which is why I (a 10.5D) still fit into the Oak Street 10D well. 

The point is: these boots are forgiving, especially for guys who normally wear an E or EE width.  

Break-in Period

oak street trench breaking in water

Each type of leather has its own break in period, but I’ve never had an issue with Horween Chromexcel boots. Even though I have the roughout Chromexcel Trench Boots, I didn’t have any discomfort or blisters with the break in at all. 

Of course, because the midsole and insole are all leather and cork, it takes a while for your foot to imprint on the insole and become truly comfortable, but I never felt the need to take a rest or take my boots off when working to break them in. 

What Do Other Reviewers Say?

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Oak Street Bootmakers has a loyal following and are still growing as a lesser-known but deeply respected brand. 

There aren’t a ton of reviews around for the Trench, but the ones I’ve found are almost unanimously positive. The only drawback I found was the wider toe box, which some liked and others didn’t. 

I think the wide toe makes this a much more casual/rugged boot, but it’s not so pronounced that it’s a defining characteristic. 

Oak Street Trench Boot
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Oak Street Trench Boot Alternatives

Grant Stone Diesel

Grant Stone Diesel profile view closeup
Wearing my Grant Stone Diesel

The Grant Stone Diesel is a worthy alternative to the Oak Street Trench. It’s also a plain toe service boot made with Horween Chromexcel, though the toe is a little more narrow and sleek. 

There are some E and EEE sizes available with the Grant Stone Diesel, and a few different leather colors as well. 

Quality-wise, I’d say the Diesel and Trench are on a level playing field. The styles are a bit different, and the Grant Stone Diesel is roughly $80 less expensive (price varies depending on the leather selection you make). 

The biggest difference is that Oak Street Bootmakers manufacture their boots in the USA, and Grant Stone makes theirs in China. While China isn’t known for high quality, I must make it clear: Grant Stone boots are really well built. The construction and material quality is generally equal between Grant Stone and Oak Street. 

But if value for money is your top concern, consider the Grant Stone Diesel. If locally made is more important, then the Oak Street Trench is the way to go. 

Grant Stone Diesel
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My Thoughts Overall On the Oak Street Bootmakers Trench

What I Like

  • The Trench is made in several varieties of Horween Chromexcel, plus a few that are more rare (I got the Natural Roughout Chromexcel).

  • The construction and overall material quality is outstanding. 

  • Oak Street is made in the USA and most of their materials are domestic, too. 

What I Don’t Like

  • I wish these had speedhooks—I love speedhooks. 

Who is the Oak Street Trench for?

The Oak Street Bootmakers Trench Boot is perfect for someone who appreciates the small details like high quality materials, stitching density, and is interested in wearing a pair of boots for 10 or more years. Plus, if you like USA-made products, you’ll dig these American-crafted beauties.

The Verdict

I’m happy with my Oak Street Bootmakers Trench Boots. They strike a nice balance between being rugged, durable boots, without being so big and bulky that they look awkward with slim fit jeans. These are versatile boots, both from a style standpoint and also from a general life perspective (I’ve worn mine to coffee shops, scrambling through a river, hiking, and on dates with my wife). 

I think they particularly look good if you’re wearing some green chinos or canvas pants—if you can play up the military aesthetic a bit more, it’s only going to work in your favor with this style of boot. 

The construction and material quality is superb. I’m going to have these boots for a decade or longer. With a Goodyear welt (Barbour, no less), Dainite sole and toplift, and pure natural insole and midsole, these might look simple, but they’re built like tanks.

Oak Street Trench Boot
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If you’d prefer to watch my review of the Oak Street Trench, check out the video below: