Initial Impressions, Oak Street Bootmakers, Stitched Footwear

Oak Street Bootmakers Trench Boot: Shell Shocked

Price: $442-548

Why Buy?

The Oak Street Bootmakers Trench Boot offers a different take on the service boot with an amazing last and interesting material options.

Why Avoid?

The Oak Street Bootmakers Trench Boot construction method can be less waterproof than most goodyear welt boots.


ModelTrench Boot
Height6.75 inch
MaterialsWaxy Mohawk Leather / Dainite Outsole
Weight813 g / 1 lb 12.7 oz
ConstructionGoodyear Welt
Country of OriginUnited States of America


Oak Street Bootmakers Logo

When does a footwear company go from start up to established brand? Oak Street Bootmakers has only been around since 2010. I bet there are people reading this page who have socks older than this brand. However, when taking a look at the market, there are now countless brands trying to do to Oak Street Bootmakers what they did to Alden and Allen Edmonds. Truman, Grant Stone, Parkhurst, and more all followed the path set forward by Oak Street Bootmakers. I thought it might be worth going back to the genesis of Oak Street Bootmakers, one of their first models – the Trench Boot.

If you’re not familiar with the brand, Oak Street Bootmakers was founded by George Vlagos.  Vlagos, son of a Greek-born immigrant who worked as a cobbler in Chicago, originally built the brand as a white-label shop. Contracting out all their models to various factories. Over time, however, the brand grew large enough that they started to buy factories themselves.

In fact, they famously saved the highland shoe company factory. Buying it and preserving the jobs of the team who worked there. If you’re interested, a review on a pair from that factory can be found here.


While this pair of boots were not made in that factory, it still got me thinking. After all that growth, has Oak Street Bootmakers started to rest on their laurels? Have they become the complacent ones? Let’s take a look at their very first offering and find out.



Oak Street Bootmakers Trench Boot
Oak Street Bootmakers Trench Boot

Let’s get one unfortunate thing out of the way. You can’t buy this version of the Oak Street Bootmakers Trench Boot. One of my favorite things about this brand is that they can get adventurous and offer really unique make ups like this one. The flip side of that is once that make up is sold out, they move onto something else.

All that being said, the leather on this boot is crazy. Not for the squeamish, you can see the veins, scars, and history of the cow which offered it. It’s definitely a love-it-or-hate-it leather. Personally, I think it’s great and I’m excited to have a pair. Mrs. 100wears hates it, and said looking at it makes her uncomfortable.  

Moving on from the leather, the shape of this shoe is not what you expect. First, the cut of the boot is really high. Measured from the welt to the top of the boot, these are actually the highest boots we’ve reviewed. Most fashion-focused boots (Alden Indy, Viberg Service Boot) are around 5 inches. The work/fashion hybrids (White’s MP, Nick’s Americana) default to 6 inches. These boots are 6.75 inches in height!

Waxy Mohawk Leather
Look at that texture!

This height is juxtaposed to a fairly close-cut boot elsewhere. An exterior heel cap wraps around a narrow heel, expanding out to a wide but form fitting toe box. This pair doesn’t have a cap toe, but it’s an option if that is your preference.


Inside, the boot is half lined – unlined in the shaft, but lined up by the toe box. This is generally my preferred make up in a pair of boots, but some do prefer fully lined.

Leather laces are the only ones that come with the boots, and come installed in the 8-tall metal eyelets.

Mid- and Outsole:

The bottom half of the Oak Street Bootmakers Trench Boot is fairly basic. A natural colored 360-degree welt runs the entire length of the shoe. The stitching on it is clean overall, with just one minor bit of fraying at the joint on one boot.

Oak Street Bootmakers Welt
Can you find the welt joint?

Speaking of the joint, they are extremely clean. When I took them out of the box, I genuinely had to make sure they were not blake-rapid as the welt looked more like a flat midsole.

My only major complaint about the boot comes here though. The way Oak Street Bootmakers lasts their boots, the interior welt stitching (connecting the gemming to the welt) is often slightly exposed. While not a structural issue, this exposed stitching can get wet and pull water inside the boot. If you’re planning on wearing this boot in heavy rain, many of those cap toe models also have a storm welt.


Moving down, the full leather midsole is attached to a black studded Dainite outsole. Again, nothing to complain about with the stitching here. A ¾ inch heel with two leather stacks and a Dainite cap finishes everything off.


OSB Boot
Oak Street Bootmakers Trench Boot

Visually, the Oak Street Bootmakers Trench Boot offers a really interesting take on a service boot pattern. Being both tall and close cut, it can straddle the outdoorsy vibe while also being able to pull double duty as a slightly dressy option when pants cover the top.

While this particular leather lands the boot strictly in the casual side, the other choices are much more versatile. In a brown chromexcel, this boot could easily go from weekend warrior to a semi-casual office environment. In fact, I’d say the Trench Boot works better with chinos and an OCBD/Polo than jeans and a t-shirt.

Fit & Comfort:


Elston last
Toe Shape

The Elston last, which is what the Oak Street Bootmakers Trench Boot is built on, is the definition of a combination last. These boots feature a very narrow heel, and a very wide toe box. While often derided as being like a duck bill, I’ve got to say: sorry Alden Trublance, this is my new favorite last. I almost wonder if George had a picture of me on his desk when he was designing it.

The heel does a great job of holding your ankle in place, while the wide toe box allows your toes to move freely. I’m in between an 11.5 and 12 on the brannock and for almost every lined shoe I go up. This is the first pair that going down was better. It fits me like a glove.


I should say that while the toe box is wide, the boot is not particularly long. If toe box is often the deciding factor in your boots I’d suggest rounding down. If it is not and another factor determines your size – such as if you have wider ankles or long, narrow feet, I would suggest rounding up.

I took these in a size 11.5. For comparison, I take a size 12 in the Alden Barrie, 11.5 E in the Viberg 2030, and an 11.5 E in the White’s 55 last.

For a full list of sizing in every shoe we’ve reviewed, click here.


Oak Street Bootmakers Heel
Small heels keep your foot in place

My love for the last that Oak Street Bootmakers used on the Trench Boot aside, the comfort in this boot is middle of the road. Arch support is right in the middle of the average high-end boot, and the slimmer mid and outsole offer great flexibility at the trade off of less impact protection.

I wouldn’t plan on using these for a 10 mile hike, but your dogs won’t be barking at the end of a normal day.


Of course, you can’t ignore the last. Being able to have a boot grip your foot without slip, while also letting your toes move is simply divine. Throughout the day, your feet will do a good job adapting to whatever level of padding is in the boot. However, they will not be able to get used to blisters on your heel or crunched toes.

Materials & Construction:


Dainite outsole
Dainite, leather, dainite, leather, different (softer) leather

Oak Street Bootmakers does a much better job than most explaining what is in their shoes, and they should be commended for that.

The uppers for the Trench Boot generally come from two places – Horween Leather and C.F. Stead. This particular pair is C.F. Stead Waxy Mohawk (even if Oak Street Bootmakers included the Horween tag with them). This leather is actually a bit thinner than most boots reviewed here, coming in at around 1.5 MM. Punched into the leather, metal eyelets hold thick rawhide laces.

Horween tag
At least the care instructions are the same…

Underneath, a veg tanned leather insole is capped with a leather heel cap. Continuing down you have a cork layer with a fiberglass shank. A leather midsole and Barbour welt are sewn to a Dainite outsole, finishing off the package.

The materials here are all top rate and leave nothing to complain about. Really, the only thing some may complain about is the fiberglass shank, but as someone who regularly goes through metal detectors, they are a big win to me.



Exposed goodyear welt
Goodyear welt with exposed internal stitching

Oak Street Bootmakers uses a 360-degree goodyear welt on all of their Trench Boots. If you want the full explanation of that, click here. However, the cliff notes version is that the upper is attached to a piece of leather (called a welt). This welt is then sewn onto the outsole.

Most people would consider a goodyear welt the best all-around option for constructing boots in this price range. Offering easier resolablity and weather protection than blake or stitchdown, and not being quite as laborious as true handwelting, it lands in a great middle ground. It isn’t surprising it’s the most common construction method among quality footwear.

Ease of Care:

Dainite Outsole
Goodyear welted Dainite outsole

While you can’t find the waxy mohawk leather anymore, this type of leather follows the same care pattern as their most common leather for the Oak Street Bootmakers Trench Boot – chromexcel.

First, you’ll want to make sure you keep shoe trees in the boot when you’re not wearing them. This will help keep creases out, as well as keep the toe from curling and more than it already does.

Next, you’ll want to be sure to condition the boots somewhat regularly. Exactly how often will depend on how you use your boots and your environment, but every 4 to 6 months is a good rule of thumb. I personally prefer Bick 4 – it does a great job, doesn’t darken the lather, and costs a bit less than other brands of conditioner. Horween and Oak Street Bootmakers suggest Venetian Shoe Cream. You really can’t go wrong with either.

Finally, when the boots have been put through the ringer, their goodyear welt construction makes them easy to resole. Oak Street Bootmakers offers a full recrafting service, where they will also touch up the uppers. The price ranges from $120 for a leather sole to $150 for Dainite or Wedge. You can also take them to your local cobbler, but with the recent inflation you’ll likely to pay the same or more.

Pricing & Value:

Trench Boot height
Higher than you think

Depending on options, Oak Street Bootmakers Trench Boot costs anywhere from $442 to $468. The Cap Toe with a storm welt comes in at the same price. Limited edition models are generally a bit more, and depend on their make-up. If you’re wondering what Oak Street Bootmakers has at the moment, click here.

That is actually amazingly close to their initial price. You can still find the StyleForm thread where they launched for $422. Adjusted for inflation that’s $521.

Their current pricing puts them in the same price point as boots like the Allen Edmonds Higgins Mill and Truman’s offerings. I’ve personally had less than stellar experiences with both brands, and wouldn’t recommend either over the Trench Boot.

Oak Street Bootmakers laces
Thick rawhide laces included

Really, the decision should be if it’s worth going up to something like White’s or down to something like Grant Stone. White’s competitor would be the White’s MP (Full Review Here) for around $150 more, and the Grant Stone would be the Diesel for around $150 less. All three are great options, your budget should determine the call.

Of course, you can also consider other boots in the Oak Street Bootmakers’ line. The Field Boot uses the same last as the Trench, but comes with a one-piece heel panel and a lower cut. The Lakeshore Boot comes with a more elegant last, and full leather lining. Up to you if you consider those an upgrade or not.

It should be noted that Oak Street Bootmakers regularly run sales. What is included seems to be based on what is sitting around in their warehouse at the time, but it’s definitely worth checking their website on the traditional sale holidays (President’s Day, Labor Day, Black Friday, etc.) for deals.

Wrap Up:

Oak Street Bootmakers Trench Boot
Oak Street Bootmakers Trench Boot

At the top we asked if the Oak Street Bootmakers Trench Boot was still worth looking at, and I have to say the answer is yes. Setting aside that the last was carved to exactly match my foot, the Trench Boot brings a lot of unique features in at a competitive price point.

My only major complaint – the exposed internal stitching – can easily be solved by opting for a model with a storm welt. Though, I would encourage Oak Street Bootmakers to just make the storm welt standard across the range.

If you’re thinking of picking up a boot sometime soon, be sure to keep Oak Street Bootmakers on your list.

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