Oak Street Bootmakers Trench Boot vs R.M. Williams Comfort Craftsman

102 facts in comparison

Based on 203 Reddit opinions. Close race—Trench Boot edges ahead.

203 opinions
Trench Boot leads by 3pts
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.

Check prices
VS
R.M. Williams Comfort Craftsman
70%
B-
Based on
270 Redditors

R.M. Williams Comfort Craftsman

~$539
114 opinions

tldr; Australian Chelsea boot icon. One-piece leather construction. Perfect for smart casual.

Check prices
Leather QualityConstructionComfort & Break-inDurabilityFit & Sizing
LEA
CON
❤️COM
🔧DUR
📐FIT
63
Points
53
Points

Score by Category

Leather Quality
100%50%
Construction
38%35%
Comfort & Break-in
89%75%
Durability
50%75%
Fit & Sizing
46%44%

Why is Williams Comfort Craftsman better than Bootmakers Trench Boot?

  • Better durability (75% vs 50%)
  • Australian icon Chelsea boot
  • Wholecut construction, 8+ year lifespan
  • Comfort insole divisive among owners
Based on 571 Reddit opinions
Too Close to Call

Reddit prefers the Trench Boot

Winning by 3 points (73% vs 70%)

Better leather quality
Better comfort
Better value
High confidence (571 mentions)

💬Reddit Sentiment

Based on 571 Reddit mentions

Overall Rating

Trench Boot
7.3/10
301 mentions
Comfort Craftsman
7.0/10
270 mentions
LEATHER QUALITY
Trench Boot10.0/10
Comfort Craftsman5.0/10
CONSTRUCTION
Trench Boot3.8/10
Comfort Craftsman3.5/10
FIT
Trench Boot4.6/10
Comfort Craftsman4.4/10
COMFORT
Trench Boot8.9/10
Comfort Craftsman7.5/10
DURABILITY
Trench Boot5.0/10
Comfort Craftsman7.5/10
VALUE
Trench Boot5.7/10
Comfort Craftsman4.0/10
⚔️

Head to Head

Head to Head

Trench Boot: 4|Comfort Craftsman: 1
Leather QualityTrench Boot
Trench Boot100%
Comfort Craftsman50%
ConstructionTrench Boot
Trench Boot38%
Comfort Craftsman35%
Fit
Trench Boot46%
Comfort Craftsman44%
ComfortTrench Boot
Trench Boot89%
Comfort Craftsman75%
DurabilityComfort Craftsman
Trench Boot50%
Comfort Craftsman75%
ValueTrench Boot
Trench Boot57%
Comfort Craftsman40%
Trench Boot73%
Comfort Craftsman70%
Close race - Trench Boot edges ahead by 3 points

Key Specs

SpecOak Street Bootmakers Trench BootR.M. Williams Comfort Craftsman
Construction
Goodyear welt
Hand-crafted from a singular piece of leather, Goodyear welt
Leather Type
Horween Chromexcel leather
Last
Elston last
Sole
Dainite studded soles or other options
Non-Slip, Oil Resistant Composite Rubber Sole
Toe
Cap-toe with freehand brogueing

Key Highlights

Oak Street Bootmakers Trench Boot
🇺🇸 Made in Chicago, IL
🎨 Horween Chromexcel leather
🪡 GYW construction
💰 $400-450 range
📏 Elston last runs TTS
R.M. Williams Comfort CraftsmanWinner
🇦🇺 Australian icon Chelsea boot
💪 Wholecut construction, 8+ year lifespan
🧰 Comfort insole divisive among owners
📉 QC concerns raised in recent years
💸 Retail >$500, look for sales

Topic Battles

Trench Boot: 3|Tied: 1|Comfort Craftsman: 1
Leather Quality
Trench Boot wins
Trench Boot
100%
Comfort Craftsman
50%
Construction
Trench Boot wins
Trench Boot
38%
Comfort Craftsman
35%
❤️Comfort & Break-in
Trench Boot wins
Trench Boot
89%
Comfort Craftsman
75%
🔧Durability
Comfort Craftsman wins
Trench Boot
50%
Comfort Craftsman
75%
📐Fit & Sizing
Trench Boot
46%
Comfort Craftsman
44%

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
View
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

What Redditors Say

Best praise vs top criticism for R.M. Williams Comfort Craftsman

Best Praise
+19 pts
RM Williams comfort craftsman are significantly more comfortable in my opinion. Objectively they are much more formal and subjectively I think they are a lot better looking compared to blundstones as well. However they are quite pricey, but worth it imo.
r/malefashionadvice
View
Top Criticism
+13 pts
RM Williams aint gonna cut it for any wet outdoor conditions. I tried walking with it on a short footpath with mud and had water ingress. The leather soles don't have traction and will get annihilated by wet and rough terrain.
r/malefashionadvice
View
3 more quotes available below

📈Historical Price Data

R.M. Williams Comfort Craftsman
R.M. Williams Comfort Craftsman

Which is Better?

Oak Street Bootmakers Trench Boot Wins
73%
Boot
vs
70%
Craftsman

Close race, but Oak Street Bootmakers Trench Boot edges ahead by 3 points based on 571 Reddit opinions.

Why Trench BootWinner
  • Better Value for Money (57% vs 40%)
Why Comfort Craftsman
  • 🇦🇺 Australian icon Chelsea boot
  • 💪 Wholecut construction, 8+ year lifespan

❤️The Love/Hate Breakdown

Sentiment Breakdown

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

Sentiment Breakdown

29%Positive
Positive
29%
Neutral
58%
Negative
13%
Based on 270 Reddit opinions

Frequently Asked Questions

Which is better, Oak Street Bootmakers Trench Boot or R.M. Williams Comfort Craftsman?
Based on 571 Reddit comments, Oak Street Bootmakers Trench Boot has a slight edge with 73% positive sentiment vs R.M. Williams Comfort Craftsman's 70%. The difference is small, so both are solid choices.
Should I buy Oak Street Bootmakers Trench Boot or R.M. Williams Comfort Craftsman?
Both have similar approval ratings (73% vs 70%), 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 R.M. Williams Comfort Craftsman?
Reddit users highlight: Australian icon Chelsea boot. Wholecut construction, 8+ year lifespan. Comfort insole divisive among owners. With 270 mentions and 70% approval, it remains a popular alternative.
How many Reddit reviews were analyzed?
This comparison analyzed 571 Reddit comments: 301 about Oak Street Bootmakers Trench Boot and 270 about R.M. Williams Comfort Craftsman. 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.

203 Reddit opinions analyzed · Last updated 7/27/2026