Oak Street Bootmakers Trench Boot

$$ Mid-rangeTrending Down

tldr; Chicago-made luxury boots. Trench boot is the icon. Natural CXL ages beautifully.

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Sentiment Breakdown

21%Positive
Positive
21%
Neutral
71%
Negative
8%
Based on 301 Reddit opinions

Strengths & Weaknesses

Each axis shows what % of Reddit comments are positive about that topic. Higher = more praise.

Key Features

  • Inspired by WWI M1917 Army boot
  • Handcrafted entirely in the United States
  • 100% recraftable design
  • Horween Chromexcel leather for durability and patina
  • Elston last for comfort and fit
  • 🇺🇸 Made in Chicago, IL
  • 🎨 Horween Chromexcel leather
  • 🪡 GYW construction

Sentiment Over Time

50%75%100%Apr '25Jun '25Aug '25Oct '25Dec '25Jan '2673% (Apr '25) - 19 comments79% (May '25) - 19.8 comments100% (Jun '25) - 9.6 comments50% (Jul '25) - 6 comments62% (Aug '25) - 18.9 comments100% (Sep '25) - 4.9 comments100% (Oct '25) - 10.3 comments67% (Nov '25) - 8.3 comments100% (Dec '25) - 6 comments50% (Jan '26) - 2 comments

What Redditors Actually Say

What Redditors Say

Best praise vs top criticism for Oak Street Bootmakers Trench Boot

Best Praise
+10 pts
Recently got these OSB trench boots in black CXL on sale, thought I'd post some initial thoughts here for discussion. Sizing: 8E/EE brannock with wide instep and narrow heel, followed their sizing guide and got size 8 in their Elston last. Fit: The fit is quite nice, nothing much to complain here. They are very snug/slightly tight out of the box all-round without any pressure points. It has been a little over a week of daily wear and the CXL is breaking in very nicely. Virtually no heel slip, would like a little more room in the toe box but this is not bad at all. Style/build: I strongly disagree with those who say these look like duck feet. That said, they are definitely not the most sleek silhouette out there. My frame of reference is quite limited as I am relatively new to heritage/GYW boots, but I'd rate its shape above the old Thursday RT3 last which I own and was famous for being too round at the front. Like what Thursday did with the new Kingmaker last, (as well as the parkhurst 602M) I think the Elston would benefit stylistically from a slightly elongated toe box to match the added width and maintain a more almond-shaped toe. That said, this his is only my opinion, and I am still happy with how these look as-is. I did put some new flat cotton laces on instead of the factory raw hide laces, but that's just a personal preference. In terms of build, I would really appreciate at least one more set of speed hooks (these have two) to help taking them on and off. These also have ungussetted tongues. I would prefer a semi-gussetted tongue, but it's not a make-or-break for me. Finish/QC: I feel like I have seen a disproportionally high number of posts and comments regarding OSB's shoddy finish and QC. I am happy to report that I cannot spot any defect/QC issues that are worth mentioning. My only nitpick is that the break/creasings on the vamps are not the best (as you can probably tell from the pictures), and that the quarters somehow have better, more "buttery" creases. I am happy to sweep this under the carpet of "CXL lottery", but maybe this can be improved by better clicking. Final thoughts: In terms of finishing and feel, I would say these feel less premium and well-made than the pair of Parkhurst I own, which is in the same price bracket as OSB but quite a bit cheaper at MSRP. Note that OSB is made in USA and Parkhurst is made in Spain, so that may be a point of consideration for some. I have read that both Grant Stone and Parkhusrt are better made than OSB in the same-ish price range, but again, only OSB is made in USA. All in all, I think these are OK for the price I paid, though I am not too sure if I would pay the full MSRP knowing the QC risks. If QC is not an issue and they add a semi-gusseted tongue, I would 100% buy them again and recommend them to others.
r/goodyearwelt
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Top Criticism
+4 pts
I really dislike how I see so many bad clicking when it comes to OSB. Happened to me. Love the silhouette of their boots though.
r/goodyearwelt
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13 more quotes available below

Frequently Asked Questions

Is the Oak Street Bootmakers Trench Boot worth buying?
Chicago-made luxury boots. Trench boot is the icon. Natural CXL ages beautifully.
What do Redditors love about the Oak Street Bootmakers Trench Boot?
Redditors highlight: 🇺🇸 Made in Chicago, IL. 🎨 Horween Chromexcel leather. 🪡 GYW construction.
What are the downsides of the Oak Street Bootmakers Trench Boot?
Some criticisms include: "I really dislike how I see so many bad clicking when it comes to OSB. Happened to me. Love the silhouette of their boots though."
How accurate are these ratings?
Our sentiment analysis is approximately 80-85% accurate compared to manual review. Products with more mentions (Oak Street Bootmakers Trench Boot has 301) tend to have more reliable scores.

301 Reddit opinions analyzed • Last updated 4/10/2026