REVIEW: Oak Street’s Trench Boot! Does the Cost Match the Quality?

Oak Street is a relatively new boot company founded in 2009 and it has Chicago in its DNA — everything is made with material from the city’s Horween Leather Company and Oak Street is even named after an area in its Gold Coast neighborhood.

The Trench boot is their most popular boot and the most popular leather for it is Natural Chromexcel. Let’s dive in.



This has a really uncomplicated, plain toe, service boot aesthetic that I really liked. Some people think the toe is too “duckbilly” but I find it’s the kind of minimalist boot that let’s the construction and the leather quality speak for itself. It also comes with rawhide laces which normally I’m not a fan of, but I think the color works great with the natural leather.

Otherwise the leather is a gorgeous blonde, the sole is a slick Dainite rubber, it’s partly lined with calfskin, and there’s enough stitching to suggest it’s well made without trying too hard in the durability category.



Quality control-wise I had no issues with the leather at all: zero loose grain, zero premature creasing. The leather wears well and it looks great, unlike my Wolverine 1000 Miles which creased a ton.

*** See more in my Wolverine Vs Thursday video: ***

This is natural Chromexcel®, a combination tanned leather that undergoes 89 processes taking 28 working days to make using all five floors of Horween’s facility. The leather is a little over 2 millimeters thick and what’s cool about natural leather is that it doesn’t show scratches or creases quite as easily as a brown boot.


The outsole is Dainite, a great combination of grip, durability, and flexibility. It’s also way easier to clean than a leather sole and it looks a lot better as it ages.

After the Dainite there are oiled leather waterlock soles, which is one reason this is a particularly water resistant boot. Another is the 360-degree Goodyear welt, which puts a canvas rib between the upper and the sole and allows for easier resoling.

*** Like simple service boots? See my comparison of ALDEN VS ALLEN EDMONDS VS GRANT STONE: ***


Sizes run from 7 to 14 and there’s just one width available right now, so wide or narrow feet are out of luck. They fit true to size, so no need to order a size down here.

I had no issues wearing these in, but I will say my toes tended to slide down to the end of the boot, which I didn’t like.


This can change, but right now it’s $462 for a pair of these with the Dainite sole. They’re more expensive with a toe cap and less expensive with leather soles, so you have options.

*** Is the very pricy Viberg worth $700? Find out in my video: ***


Great quality leather
Simple aesthetic
Unusually water resistant

Not the best fit
Just one width available


Dragonetti Luis says:

Do this pairs have a steel shank or something like that ?

Seth _ says:

I’ve had a pair of these in black with dainite for a couple of years. He’s correct about sliding forward in them. It’s horrible. After I put some Dr Scholls in there to deal with the lack of arch support, the sliding stopped and now they are super comfortable. They look like they would be bulky and heavy but they’re not heavy. There is loose grain on one of the quarters which annoys me, but at least it’s on the outside and I don’t have to see it much.

Matthew Hopkins says:

Love your channel, keep up the awesome vids!

Zahinn says:

But Nick, are there really any high end boots out there that are actually fairly priced?
I feel they all bump the price about 50 to 150 bucks.

Andrew H says:

What is the name of the boots pictured in the top right corner of your intro (0:02) with grey pants?

Marc Possoff says:

Seems like you’re paying for quality with Oak St. like you said they’re selection. of CXL is pretty good.

Puneet says:

Another great review. Well done. Just wondering if you’d consider starting to do some reviews on dress boots like the Dalton from Allen Edmonds?

bigbat21 says:

What do you mean when you say “loose grain” ?

chuck lan says:

Review white’s mp boots sometime ?

boluno says:

Once again, another really good review! Thanks for the info. They look a lot alike my natural AE Higgins Mill.

K Chan says:

HEY HEY! Been waiting for this review! Glad you liked them. I love the fit on both my pairs. I have quite wide feet and they fit me perfectly. Got a pair with leather sole and another with Dainite. I do prefer the feel of the leather sole. Another great vid mate. Keep up the stellar work!

Super vidal says:

Can you make a vid about EU boots?? Pls from affordable to expensive waterproof pls

Ed F says:

Another great video Nick! Always happy to hear your thoughts, both pro and con, on the shoes you review. While perusing Oak Street’s website a while ago, I discovered that they sell Venetian Leather Cream at unbelievably reasonable prices. I’m wondering if their very reasonable pricing of Venetian Leather Cream might be suggestive that their boots are priced fairly. Wondering your thoughts on this matter, given your comments and belief that their Trench Street Book might be a bit pricey. Just a thought. Again, very nice review and video.

Jonathan Mahan says:

@Stridewise I would love to see a Thursday Vanguard review! I just purchased a pair recently and I’m having doubts. I could have paid a little more to get a solid work boot or I could have spent a little less on a solid fashion boot. The Vanguards are in that awkward middle territory. One boot also shipped with some loose grain, but I didn’t want to bother going through the refund/ exchange process since there’s no telling if the next boots would be in better or worse condition. This is coming from someone without much boot experience, as this is only my second pair of boots. I just need to feel validated in my choice of picking the Vanguards over the Captains haha. Great review by the way, as always!

MetalsForBrunch says:

This shoe or the helm zind natural?

Greg Kosinski says:

I want their Summit boots. Someday…

Kubensis says:

I got a pair of black lake-shores for $200!

I put dr sholls in mine to make them not slide around, they are SO slippery on the inside. i dont even know if they are my size or if theyre just so slippery lol.

Mines the one for extra arch support… i think theyre advertised towards people with bad pain in the foot? Don’t remember, works amazingly well, theyre super snug now on my foot.

Do you have any recommendations on how to style black, leather sole lakeshores?

I have khaki, and olive chinos, and i have dark slub denim. I don’t want to embarrass myself – first pair of boots ever.

Azael Contreras says:

This is a great review, but I have a question as to how long it takes to have the cork bed midsole form to your feet on your pair of Thursday boots. Also on my pair of Thursday’s, there seems to be little dents on the inside of the shoe at the heel area. They seem to match the little metal things at the bottom of the heel, idk if this is bad or something… they also kinda wrinkle, like the tiny wrinkles when you bend… I’m new to this. And the Eva comfort strip seem to offer no comfort for me, kinda just makes the bottom feel smooth. Did you experience any of these things around the start of when you got your pair?

swellingsuperman says:

I’m going to go broke because of you

WatchAficionado says:

I have these. Beautiful boots and well made. I do wish the height of the toe box was a little more. I suspect as I wear these, they will get more comfortable.

Isaac Lara says:

I’ve been wanting a pair of oak street boots but the 460 dollar price tag holds me back. I’ve looked at Thursday but seen mixed reviews. Any recommendations in the price bracket between Thursday and oak street?

Kevin Leyva says:

I own a pair in brown with the leather sole and I love them. A bit nicer than the 1,000 miles imo. Tho I do agree that the “stacked leather” heal doesn’t look like leather and at first I thought it was plastic since I didn’t see any grain orientation. I own about 50+ pairs of boots, mostly heritage type, and I was looking to add the Thursday president in black and the Thursday Vanguard (which is $60-ish more). Would love to see you thoughts on the Vanguard since you enjoy the Captains.

DEXVD says:

At a similar price point how do you feel these would compare with the Grant Stone boots?

Hameed says:

You should do a giveaway for the redwing boots or Any kind of giveaway seriously come on let me at least get the chance to own one pair of the these boots you review on your channel

P Hawj says:

Nice vid. One of the boots that I’m gonna pull the trigger on. Just a question on pairing them with a nice Jean. I normally have darker color boots (not black) with darker color jeans (not black either). Would you pair these natural boots with a dark color nice fitted jean or would your tan/ green etc colors work better?

Noxus Designs says:

Thursday Boots Vanguard? I really hope they release a pair with natural chromexcel

Daniel Brice says:

Isn’t this an EXACT copy (CXL, Dainite, cut and style) of AE Higgins Mill but for $60-80 more (at full msrp)? AE sells the Higgins Mill for $300ish right now on sale …

Ricardo Serrano says:

Hey Nick, first of all great videos. I’ve binge watch all the videos haha. In my honest opinion best complete reviews. Enjoy how you always incorporate both positive and negative aspects of the boots you review. Also enjoy your implication of the boots to everyday situations. I purchased a pair of Thursday Captain Natural thanks to your recommendation. Anyhow, is there a chance for reviews in the future about either harness or engineer boots? Are those outside of your taste in boots? I would jump with joy to see you do a review of some. Looking at Frye John Addison boots at the moment. Thanks and greetings from San Diego, CA 🙂

sleepingbear says:

They are gorgeous indeed and seem very well made but, as far as i’m concerned, there are too many (good)options below that price point nowadays. If i can find a good deal i’ll be all over them though.

Great review as usual!!

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