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
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.
Things to Consider Before Buying
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.
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.
My Hands-On Review
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.
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
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.
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.
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.
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.
I was bouldering over wet rocks and algae-covered slides, and the sole did extremely well keeping me upright.
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.
Fit and Sizing
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.
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?
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 Alternatives
Grant Stone Diesel
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.
The Grant Stone Diesel is a no-frills mid-weight boot built with superb attention to detail and materials. The quality is comparable to other boot makers who retail for $450-600, but the Diesel is much less expensive. It’s one of the better price for value buys you’ll find.
My Thoughts Overall
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.
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.
If you’d prefer to watch my review of the Oak Street Trench, check out the video below: