Oak Street Bootmakers Trench Boot vs Red Wing Blacksmith

104 facts in comparison

Based on 177 Reddit opinions. Close race—Trench Boot edges ahead.

177 opinions
Trench Boot leads by 2pts
Reddit's Pick
OS
Trench Boot
73%
B-
Based on
301 Redditors
Winner

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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VS
Red Wing Blacksmith
71%
B-
Based on
264 Redditors

Red Wing Blacksmith

88 opinions

tldr; Iron Ranger's sleeker sibling. Same quality, no cap toe. Easier to dress up slightly.

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Leather QualityConstructionComfort & Break-inDurabilityFit & Sizing
LEA
CON
❤️COM
🔧DUR
📐FIT
63
Points
65
Points

Score by Category

Leather Quality
100%100%
Construction
38%57%
Comfort & Break-in
89%36%
Durability
50%71%
Fit & Sizing
46%23%

Why is Red Wing Blacksmith better than Bootmakers Trench Boot?

  • Better durability (71% vs 50%)
  • Better construction (57% vs 38%)
  • Better value (100% vs 57%)
  • Briar Oil Slick leather classy with conditioning
  • Resolable, but 430 mini-lug stiff
  • Size down 0.5 from Brannock
Based on 565 Reddit opinions
Too Close to Call

Reddit prefers the Trench Boot

Winning by 2 points (73% vs 71%)

Better fit
Better comfort
Made in Chicago, IL
High confidence (565 mentions)

💬Reddit Sentiment

Based on 565 Reddit mentions

Overall Rating

Trench Boot
7.3/10
301 mentions
Wing Blacksmith
7.1/10
264 mentions
LEATHER QUALITY
Trench Boot10.0/10
Wing Blacksmith10.0/10
CONSTRUCTION
Trench Boot3.8/10
Wing Blacksmith5.7/10
FIT
Trench Boot4.6/10
Wing Blacksmith2.3/10
COMFORT
Trench Boot8.9/10
Wing Blacksmith3.6/10
DURABILITY
Trench Boot5.0/10
Wing Blacksmith7.1/10
VALUE
Trench Boot5.7/10
Wing Blacksmith10.0/10
⚔️

Head to Head

Head to Head

Trench Boot: 2|Wing Blacksmith: 3
Leather Quality
Trench Boot100%
Wing Blacksmith100%
ConstructionWing Blacksmith
Trench Boot38%
Wing Blacksmith57%
FitTrench Boot
Trench Boot46%
Wing Blacksmith23%
ComfortTrench Boot
Trench Boot89%
Wing Blacksmith36%
DurabilityWing Blacksmith
Trench Boot50%
Wing Blacksmith71%
ValueWing Blacksmith
Trench Boot57%
Wing Blacksmith100%
Trench Boot73%
Wing Blacksmith71%
Close race - Trench Boot edges ahead by 2 points

Key Specs

SpecOak Street Bootmakers Trench BootRed Wing Blacksmith
Construction
Goodyear welt
Goodyear Welt
Leather Type
Horween Chromexcel leather
Oil-tanned or Rough-out
Last
Elston last
No. 8 Last
Sole
Dainite studded soles or other options
Toe
Cap-toe with freehand brogueing

Key Highlights

Oak Street Bootmakers Trench BootWinner
🇺🇸 Made in Chicago, IL
🎨 Horween Chromexcel leather
🪡 GYW construction
💰 $400-450 range
📏 Elston last runs TTS
Red Wing Blacksmith
👍 Briar Oil Slick leather classy with conditioning
🔄 Resolable, but 430 mini-lug stiff
📏 Size down 0.5 from Brannock
🪡 No midsole - harder underfoot
🇺🇸 Made in USA heritage

Topic Battles

Trench Boot: 2|Tied: 1|Wing Blacksmith: 2
Leather Quality
Trench Boot
100%
Wing Blacksmith
100%
Construction
Wing Blacksmith wins
Trench Boot
38%
Wing Blacksmith
57%
❤️Comfort & Break-in
Trench Boot wins
Trench Boot
89%
Wing Blacksmith
36%
🔧Durability
Wing Blacksmith wins
Trench Boot
50%
Wing Blacksmith
71%
📐Fit & Sizing
Trench Boot wins
Trench Boot
46%
Wing Blacksmith
23%

Based on Reddit sentiment across 5 categories

📈Where They Rank

💬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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3 more quotes available below

What Redditors Say

Best praise vs top criticism for Red Wing Blacksmith

Best Praise
+8 pts
I love my 3340. The blacksmith is very classic to me, and I agree that the model should be pictured in the dictionary definition of heritage styled boot, no question. CRT is pretty iconic, but Briar Oil Slick takes the cake for me as all-time favorite from SB Foot/Red Wing.
r/goodyearwelt
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Top Criticism
+16 pts
Blacksmith/Iron Ranger are classic. I just hate the lack of a midsole. It's a nonstarter for me. I love your review, and thanks for sharing. I'm glad you enjoy them so much. That's the beauty of a good fitting pair of footwear.
r/goodyearwelt
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3 more quotes available below

📈Historical Price Data

Red Wing Blacksmith
Red Wing Blacksmith

Which is Better?

Oak Street Bootmakers Trench Boot Wins
73%
Boot
vs
71%
Blacksmith

Close race, but Oak Street Bootmakers Trench Boot edges ahead by 2 points based on 565 Reddit opinions.

Why Trench BootWinner
  • 🇺🇸 Made in Chicago, IL
  • 🎨 Horween Chromexcel leather
  • 🪡 GYW construction
Why Wing Blacksmith
  • Better Value for Money (100% vs 57%)

❤️The Love/Hate Breakdown

Sentiment Breakdown

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

Sentiment Breakdown

23%Positive
Positive
23%
Neutral
67%
Negative
10%
Based on 264 Reddit opinions

Frequently Asked Questions

Which is better, Oak Street Bootmakers Trench Boot or Red Wing Blacksmith?
Based on 565 Reddit comments, Oak Street Bootmakers Trench Boot has a slight edge with 73% positive sentiment vs Red Wing Blacksmith's 71%. The difference is small, so both are solid choices.
Should I buy Oak Street Bootmakers Trench Boot or Red Wing Blacksmith?
Both have similar approval ratings (73% vs 71%), so focus on specific features, pricing, and what matters most to you.
What do Redditors love 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's a well-regarded choice in the community.
What do Redditors say about Red Wing Blacksmith?
Reddit users highlight: Briar Oil Slick leather classy with conditioning. Resolable, but 430 mini-lug stiff. Size down 0.5 from Brannock. With 264 mentions and 71% approval, it remains a popular alternative.
How many Reddit reviews were analyzed?
This comparison analyzed 565 Reddit comments: 301 about Oak Street Bootmakers Trench Boot and 264 about Red Wing Blacksmith. 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.

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