Oak Street Trench Boot Review – Simple Yet Luxurious

Oak Street is a much talked about footwear company that was founded in 2009 by George Vlagos in Chicago. This company has the Windy City in its DNA: most of its boots are made with leather from Horween, one of America’s most beloved tanneries that we’ve visited in Chicago, and the company’s even named after a short street in the city’s Gold Coast neighborhood.

Everything is handcrafted in the United States and many of their most popular shoes are handsewn moccasin-type shoes. But overall, the company’s most popular item is their super versatile Trench boot.

So let’s dive in.

Oak Street’s Trench Boot: Pros and Cons

Got somewhere to be? Here’s our list of who should and shouldn’t consider the Trench boot so you can get a quick need-to-know right now.


  • Simple, versatile design
  • Wider toe box is very comfortable
  • Made in USA
  • Suitable for D or E width feet
  • Pretty fairly priced; American boots like this are rare for under $500
Simple Yet Luxury
Oak Street Bootmakers Trench Boot

Oak Street might make America's best luxury city boot. Sturdy and durable but not too heavy or casual, it also has a deceptively wide toe box for extreme comfort.

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  • Not a cheap boot
  • Some prefer speed hooks on boots 
  • No narrow or extra wide sizes

Oak Street Trench Boot kicked out

Oak Street Natural Trench Boot First Glance

  • Natural Chromexcel®
  • Dainite sole
  • Simple aesthetic
  • Rounder toe box
  • Goodyear welted

The Natural Dainite Trench Boot is Oak Street’s most popular model and leather, but it comes in several other staple and seasonal leathers that have included wild boar and kudu. Expect Black, Brown, Natural, Natural Roughout, and Color 8 (burgundy) Chromexcels to be on offer just about any time.

The “Natural” leather is so named because the hide was never dyed. When you learn that, you might start thinking of the golden color as more like a chromey skin color — that’s what it is! You might think it less versatile than brown, but it matches better with black pants and they’re great with just about any trouser that isn’t khaki. (I love them with green the most.) 

The Trench has a basic, uncomplicated, service boot aesthetic, which is to say it has a low profile toe and simple lace up pattern. I’m a huge fan of the simplicity: it makes it versatile and puts the leather and construction center stage. Tall and close cut, it can put off an outdoorsy vibe while working just fine in smart casual environs.

oak street trench boot brooklyn
Braving the Brooklyn winter in Oak Streets and waxed canvas.

Goodyear welted for water resistance and resoleability, the Trench is partly lined with calfskin down in the toe box to give it some structure. It’s triple stitched along the vamp, double stitched on the heel, and single stitched everywhere else — so you can tell it’s durable, but it’s not trying too hard.

Quality control-wise, I had no issues. There was no wheeling along the stitches and no loose grain to speak of, which is extremely rare with Chromexcel leather. After a week of wear them I did wind up with a few loose threads by the heel and laces, but those are easy to burn off with a lighter. Oak Street is clearly serious about quality control.

Oak Street boots leather

This Natural Chromexcel Leather

  • Natural Chromexcel®
  • Combination tanned leather
  • Scratches are less noticeable than on brown CXL
  • May need more cleaning

This boot comes in a ton of different types of leather, but I picked he most popular kind so my review could be the most useful to the most people. (I make a lot of sacrifices, I know.)

This is natural Chromexcel®, the undyed version of America’s most beloved boot leather. Every boot company worth its salt has at least one model in this leather, which is combination tanned in Chicago by Horween Leather Company, broadly recognized as America’s best tannery

Oak Street boots dangle

A nice touch is that Oak Street includes a little booklet that lets you know how fancy the leather is: it undergoes 89 separate processes, taking 28 days and using all five floors of the Horween facility. During the production they use food grade beef tallow, cosmetic grade beeswax, marine oil, chrome salts, tree bark extracts, and lots of other secret ingredients, ultimately resulting in a slightly corrected full grain leather that’s both durable and supple.

I really want to emphasize that Oak Street, at least judging from this shoe, is really good at selecting their leather. A lot of people complain that there are too many Chromexcel boots with loose grain and I’d agree: my Wolverine 1000 Mile boots are riddled with loose grain and premature creasing. Oak Street’s leather was fantastic, showing true skill in the “clicking” process at their factory.

Natural leather hides scratches more easily than brown, though the downside of this golden leather is that dirt is more noticeable on it. Expect it to darken wonderfully with coming years and plenty of regular conditioning. Horween suggests a coat of Venetian Shoe Cream or Saphir Renovateur once or twice a year.

[Further reading: How to Clean and Care For Chromexcel Boots]

Oak Street boots sole

Oak Street Boots Sole 

  • Dainite outsole; leather also available
  • Good balance of grip, comfort, flexibility, durability
  • Leather waterlock soles
  • 360-degree Goodyear welt

The outsole is Dainite, considered the crème de la crème of rubber soles since they were launched in 1910. They’re celebrated not just for their balance of softness and durability, but also their aesthetic: while the recessed lugs offer grip, they’re perfectly flat in profile. 

The boot also comes with a leather sole at a lower price: currently $462 versus $488 for Dainite. I’m a big fan of leather soles myself, as I love their softness and flexibility, and Oak Street‘s is oiled to be more water resistant than your usual leather sole, though I concede the grip isn’t as great as a luggy Commando sole. Dainite is generally considered the best compromise between chunky lugs and soft leather with regard to softness, durability, and grip.

Oak Street boots rear view

Constructed with a vegetable tanned leather insole and midsole with a layer of cork filling between them, the Trench is a very traditionally made boot with a generous thickness to its sole materials. This build means that with time and wear, your feet will sink into the leather and cork and produce a boot that feels custom made to your foot. This custom feeling is the key to why so many guys fall in love with the world of boots.

Oak Street boots stitching and heel

Oak Street Boots Fit & Sizing

  • Runs from sizes 7 to 14
  • Just one width available, but it fits D and E
  • Order half a size smaller than your true size
  • Good weight

Right now this shoe runs from sizes 7 to 14 and there’s just one width available.

Oak Street suggest ordering true to size, though I’ve found this boot fits fine when you order down half a size like most boot brands tell you to do. Get yourself measured on a Brannock device in a shoe store and subtract 0.5 from that number. I’m an 11 in Red Wing and Wolverine and most boot brands, and while I ordered 11.5 in Oak Street and they’re perfectly comfortable, I would have a comfortably snug fit with an 11. (I’ve lent these boots to friends with feet a half size larger than mine, and they’ve loved them.) 

oak street derby
This overhead shot of Oak Street’s Oxfords, made on the same last, highlight the roundness of the toe.

The Elton last these are made on is wide at the forefoot, so it’s very comfortable and doesn’t produce any of the slight pinky pinch you might be used to if you wear other brands. The round toe also means that guys who wear E (or wide) sizes are usually comfortable ordering true to size with the Trench boot.

Some of my YouTube viewers have complained that they feel their toes sliding down into the end of the boot that they fixed with some inserts from Dr Scholl, but I didn’t have any issues myself. Just know that if you do have this issue, there’s a cheap fix from ol’ Dr. Scholl.

Oak Street boots welt

Oak Street Boot Price

  • $462 for leather soles
  • $488 for rubber soles

A nice bonus is that the price changes based on the sole, so you can “save” cash going with leather.

Now, that’s pretty pricy relative to some American-made brands like Red Wing, but they’re cheaper than higher end brands like Nicks and Whites

Oak Street deserves a seat at that table. Most Goodyear welted American boots like those brands I just mentioned are blockier and more akin to work boots, and when you’re talking Nicks and Whites, they’re often heavy to the point of unwieldy. Oak Street make a tremendous service boot that has weight (but not too much), a wide toe, and a casual elegance. The niche of “well made, great QC, not really for work but not flimsy either” is one that Viberg also falls into, and their service boots cost about $800. It’s a city boot, and a great one at that.

I don’t think this is overpriced when you consider their competition, materials, and American provenance.

Simple Yet Luxury
Oak Street Bootmakers Trench Boot

Oak Street might make America's best luxury city boot. Sturdy and durable but not too heavy or casual, it also has a deceptively wide toe box for extreme comfort.

See All Versions
We earn a commission if you make a purchase, at no additional cost to you.

Oak Street boots street

The Takeaway

There’s a lot to like about these boots. They have a clean aesthetic, super high quality leather, they’re unusually water resistant, they’ve got Dainite soles, and I love the weight of these things. Aesthetically, they’re so simple that there’s practically nothing to complain about, unless you dislike the rounder toebox. But personally, I find them unusually comfortable as a result: my Trench boots have led me to lose patience with the fit of almost all of my other boots, and once you’ve experienced the roominess, I think you’ll know what I mean. 

These boots are beautiful and comfortable, and I’m always excited when an outfit calls for them.

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Nick English

By day: Manhattan-based journalist with reporting experience on four continents, published in Vice, Men's Health, Popular Science, and a bunch of other places.By night: ravenous consumer of anything and everything related to high end men's boots.Stridewise is where I nurture a maniacal obsession with footwear and share my findings. Say hey: [email protected].

22 thoughts on “Oak Street Trench Boot Review – Simple Yet Luxurious”

  1. Great write up Nick! I’ve owned Oak Street Trench Boots and agree with you on all points You are spot on describing the leather quality, sizing, weight and overall value.
    I was especially interested in your comments on slippage. I wish I had read your review sooner, as I never found a good way to manage it.

  2. Hey, Nick….

    Oak Street Bootmakers has had a sale on their Brown Trench boots for the past couple of months. Instead of the MSRP of $425, I got a pair for $324, with leather soles. Interestingly, due to their “oil waterlock treatment,” not only were the soles more water resistant, but it also gave them a slightly gummy feel that improved traction. I experienced no slippage at all during the break in period despite walking on all type of surfaces. An unexpected pleasant surprise!

    You were on-point about every aspect of OSB boots. Their leather selection is indeed top notch. The brown Chromexcel leather on my pair is absolutely beautiful. The construction, flawless. I’ve worn them 2-3 times a week for about 2 months now and no loose threads have popped up yet. I did replace the cotton laces with rawhide ones for aesthetic reasons….my only (minor) complaint is that without speed hooks or pull-up tabs, putting them on and taking them off is a bit laborious.

    At first, I wasn’t sure how thrill I was about the “duck billy” shape, but they have grown on me with time. I love the rugged, but understated look and feel of the boots. I did notice the sliding forward sensation that you mentioned, although I hasn’t bothered me too much. With wear, I’m actually finding them more comfortable than my other boots and is fast becoming my first choice of footwear, unless I am in a rush. I think these boots will age remarkably well given the quality and thickness of leather, and the construction. Now that the weather is warming up, I sort of regret having to put the boots away soon….

    What are your thoughts between OSB and Truman? Frankly, if I were to pay $400+ for boots, I probably would have gone with a lower end Trumans that typically go for $440 or so…But $324 for an OSB was simply too hard to pass up….

    • Hey John, thanks for your well thought out comment, my friend! Good job getting such a good deal on these, sounds like their leather soles are top notch. So happy you found this review accurate. I really like the rawhide laces as well. Overall I think these are really solid boots, the toe-sliding aspect is a bit annoying but I’m generally quite happy with them and glad you found the comfort improved with time. I agree it’s a bummer when warm weather makes you shelve your favorite boots 🙂

      I’m not that crazy about Truman if I’m being honest, they’re very tough but aesthetically I find them so-so. OSB definitely more versatile!

  3. Hi there, I bought a pair of the Lakeshore boots in Color 8 Chromexcel from Oak Street and I thought I should share that there are some SERIOUS quality issues with them. The eyelets on the left boot are misaligned by about a centimeter, the stitching holding the tongue to the vamp is almost completely coming out (I had to melt the ends of the thread to prevent it from coming out further) and there are several tears near the junction between the tongue, the eyelets and the vamp. Unfortunately, I had worn them to work right out of the box before I recognized these issues. That was clearly a huge mistake.

    Considering that these are ~$490, this is ridiculous. I figured it might be worthwhile to mention this here as I’m sure a lot of people are going to be considering buying from Oak Street. Closely inspect your boots before you wear them.

    • 🙁 that sucks! I had a pair of boots with misaligned eyelets recently, it’s surprising how big a deal that can be. Did you not contact Oak Street for a return?

  4. I ordered the Oxblood Dainite Cap-Toe Lakeshore Boot back in February, 2019 and they still have not even shipped. Alden doesn’t take that long. They said the wait would be approximately 3 months, but 6 months and counting is absolutely ridiculous. If i had know that I would have found another bootmaker…

  5. Hey Nick, how does the weight of these boots compare to the Grant Stone Diesel boot, the AE Higgins Mill, and the White’s MP, in order of heaviness from lightest to heavy?

  6. I bought the brown dainite cap toe lakeshore this black friday since they were 25% off…called the company because it said my order was processing for the last few days. Their operations team called me to say the boots were in production and will be 4-6 weeks. This seems kind of crazy for the price point. Looks like I won’t have them this winter.

    I bought a few from Thursday and they were at my door in 5 days. OSB has some serious production/backorder issues, but I really hope it will be worth the wait.

    • Oh sorry to hear it, Michael! They’re great quality boots for what it’s worth, I’m sure you’ll be happy when they arrive — but you should have been told about that wait beforehand, winter will be half over before they arrive!

  7. Great review, those boots really look amazing. They look quite similar to Parkhurst’s boots in natural CXL which you also reviewed. How do you think the two compare? Are they on a similar level? Which do you prefer? … and with natural CXL, doesn’t it make you too aware of getting damaged by the elements, like rain? Thanks and keep up the great work.

    • Hey Alberto, glad you liked the review man! It looks a bit similar to Parkhurst but OSB a bit wider at the forefoot. The leather’s a tad thicker on OSB as well, so I guess it’s a hair more rugged. It’s up to you as to which one you prefer! Natural CXL doesn’t get stained very easily by the elements, to be honest. I guess it’ll show stains more easily, but that’s rare and you can always clean it off. Perhaps more importnatly natural cxl will darken with age, probably moreso at stress points.

      • Thanks for your reply Nick, I am big fan of your reviews. I find natural CXL very interesting and the way it ages, so I plan to get some boots at some point, and OSB and Parkhurst are top candidates. Thanks for the explanation! (By the way, I was not notified about your reply, I noticed because I read the post again).

  8. Great revieview! Any more input on the sizing? I wear a US 10 in RW Iron Rangers, any advice for the size in the Trench Boot?

  9. Nick, good summary. I have to disagree on the size.


    I don’t know what they’re talking about with this ‘true to size’ claim. I’m a 10.5 maybe an 11 in a sneaker and swim in my 10.5 danite trench boots. I got them as a gift, so no chance to return…. do yourself a massive favor if you’re going with these and order small.

    I’ve had them for a few years now and maybe worn them 3 times and have been so disappointed that it still clearly grieves me. Don’t order true to size and if you do, don’t wear them off the carpet until you’ve satisfied yourself that they’re a good fit.



  10. Hi Nick-

    I’m looking for something I can wear year round, mainly in an office environment. I’m trying to decide between Oakstreet’s trench boot and their trench oxford. I live in the Baltimore area, where it gets hot in the summer. Any advice for me, or thoughts on boots vs shoes in general?



    • Hey Ted, good choice here. I mean you’re really just picking between a boot or a shoe where all else is equal, I suppose the shoe would be more ideal for an office environment, it’ll look dressier. I have that trench oxford as well, I love the roomy toe


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