Grant Stone Brass Boot vs Oak Street Bootmakers Trench Boot

104 facts in comparison

Based on 164 Reddit opinions. Close race—Brass Boot edges ahead.

164 opinions
Brass Boot leads by 3pts
Reddit's Pick
GS
Brass Boot
76%
B
Based on
288 Redditors
Winner

Grant Stone Brass Boot

75 opinions

tldr; Best value in goodyear welt boots. Chinese made but excellent quality. Diesel boot is the standout.

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VS
OS
Trench Boot
73%
B-
Based on
301 Redditors

Oak Street Bootmakers Trench Boot

89 opinions

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

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Leather QualityConstructionComfort & Break-inDurabilityFit & Sizing
LEA
CON
❤️COM
🔧DUR
📐FIT
74
Points
63
Points

Score by Category

Leather Quality
100%100%
Construction
75%38%
Comfort & Break-in
33%89%
Durability
100%50%
Fit & Sizing
49%46%

Why is Bootmakers Trench Boot better than Stone Brass Boot?

  • Better comfort (89% vs 33%)
  • Made in Chicago, IL
  • Horween Chromexcel leather
  • GYW construction
Based on 589 Reddit opinions
Too Close to Call

Reddit prefers the Brass Boot

Winning by 3 points (76% vs 73%)

Better durability
Better value
Better construction
High confidence (589 mentions)

💬Reddit Sentiment

Based on 589 Reddit mentions

Overall Rating

Brass Boot
7.6/10
288 mentions
Trench Boot
7.3/10
301 mentions
DURABILITY
Brass Boot10.0/10
Trench Boot5.0/10
VALUE
Brass Boot8.9/10
Trench Boot5.7/10
LEATHER QUALITY
Brass Boot10.0/10
Trench Boot10.0/10
FIT
Brass Boot4.9/10
Trench Boot4.6/10
CONSTRUCTION
Brass Boot7.5/10
Trench Boot3.8/10
COMFORT
Brass Boot3.3/10
Trench Boot8.9/10
⚔️

Head to Head

Head to Head

Brass Boot: 4|Trench Boot: 1
DurabilityBrass Boot
Brass Boot100%
Trench Boot50%
ValueBrass Boot
Brass Boot89%
Trench Boot57%
Leather Quality
Brass Boot100%
Trench Boot100%
FitBrass Boot
Brass Boot49%
Trench Boot46%
ConstructionBrass Boot
Brass Boot75%
Trench Boot38%
ComfortTrench Boot
Brass Boot33%
Trench Boot89%
Brass Boot76%
Trench Boot73%
Close race - Brass Boot edges ahead by 3 points

Key Specs

SpecGrant Stone Brass BootOak Street Bootmakers Trench Boot
Last
Floyd last
Elston last
Construction
Goodyear welt (360-degree split-reverse or flat welt)
Goodyear welt
Lining
Full-grain kip leather lining
Calfskin vamp lining
Insole Midsole
Vegetable-tanned leather insole, welt, and midsole with cork filler and steel shank
Sole
Lug rubber outsole (also available with Natural wedge outsole)
Dainite studded soles or other options

Key Highlights

Grant Stone Brass BootWinner
💰 Excellent value at $350 range
🪡 GYW construction, resoleable
🎨 Crimson CXL popular colorway
📏 Leo last - size down 0.5
👍 Better finishing than Thursday
Oak Street Bootmakers Trench Boot
🇺🇸 Made in Chicago, IL
🎨 Horween Chromexcel leather
🪡 GYW construction
💰 $400-450 range
📏 Elston last runs TTS

Topic Battles

Brass Boot: 3|Tied: 1|Trench Boot: 1
Leather Quality
Brass Boot
100%
Trench Boot
100%
Construction
Brass Boot wins
Brass Boot
75%
Trench Boot
38%
❤️Comfort & Break-in
Trench Boot wins
Brass Boot
33%
Trench Boot
89%
🔧Durability
Brass Boot wins
Brass Boot
100%
Trench Boot
50%
📐Fit & Sizing
Brass Boot wins
Brass Boot
49%
Trench Boot
46%

Based on Reddit sentiment across 5 categories

📈Where They Rank

💬What Redditors Actually Say

What Redditors Say

Best praise vs top criticism for Grant Stone Brass Boot

Best Praise
+7 pts
Absolutely gorgeous boots. That kudu is spectacular. Personally, I think the Brass Boot is GS's best silhouette by a mile.
r/goodyearwelt
View
Top Criticism
+2 pts
Cool to see them next to one another. I love the black cypress teacore leather. The one thing I don’t like about the brass boot is how high on the boot the moc band is.
r/goodyearwelt
View
3 more quotes available below

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
View
3 more quotes available below

📈Historical Price Data

No historical price data available for these products yet.

Which is Better?

Grant Stone Brass Boot Wins
76%
Boot
vs
73%
Boot

Close race, but Grant Stone Brass Boot edges ahead by 3 points based on 589 Reddit opinions.

Why Brass BootWinner
  • Better Value for Money (89% vs 57%)
Why Trench Boot
  • 🇺🇸 Made in Chicago, IL
  • 🎨 Horween Chromexcel leather

❤️The Love/Hate Breakdown

Sentiment Breakdown

20%Positive
Positive
20%
Neutral
74%
Negative
6%
Based on 288 Reddit opinions

Sentiment Breakdown

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

Frequently Asked Questions

Which is better, Grant Stone Brass Boot or Oak Street Bootmakers Trench Boot?
Based on 589 Reddit comments, Grant Stone Brass Boot has a slight edge with 76% positive sentiment vs Oak Street Bootmakers Trench Boot's 73%. The difference is small, so both are solid choices.
Should I buy Grant Stone Brass Boot or Oak Street Bootmakers Trench Boot?
Both have similar approval ratings (76% vs 73%), so focus on specific features, pricing, and what matters most to you.
What do Redditors love about Grant Stone Brass Boot?
Reddit users highlight: Excellent value at $350 range. GYW construction, resoleable. Crimson CXL popular colorway. With 288 mentions and 76% approval, it's a well-regarded choice in the community.
What do Redditors say about Oak Street Bootmakers Trench Boot?
Reddit users highlight: Made in Chicago, IL. Horween Chromexcel leather. GYW construction. With 301 mentions and 73% approval, it remains a popular alternative.
How many Reddit reviews were analyzed?
This comparison analyzed 589 Reddit comments: 288 about Grant Stone Brass Boot and 301 about Oak Street Bootmakers Trench Boot. Data was sourced from Quality Boots community discussions.
How accurate are these ratings?
Our sentiment analysis is approximately 80-85% accurate compared to manual review. Well-discussed products with many mentions tend to have more reliable scores than niche items with fewer data points.
Why trust Reddit over professional reviews?
Reddit users bought products with their own money and have no incentive to mislead. You're seeing hundreds of real opinions across different use cases, not just one reviewer's take. This crowdsourced approach surfaces both common praise and recurring complaints.

164 Reddit opinions analyzed · Last updated 7/28/2026

Grant Stone Brass Boot vs Oak Street Bootmakers Trench Boot | reccs.co