Grant Stone Diesel Boot vs Oak Street Bootmakers Trench Boot

104 facts in comparison

Based on 282 Reddit opinions. Close race—Diesel Boot edges ahead.

282 opinions
Diesel Boot leads by 4pts
Reddit's Pick
GS
Diesel Boot
77%
B
Based on
690 Redditors
Winner

Grant Stone Diesel Boot

~$334.95
193 opinions

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

Check prices
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.

Check prices
Leather QualityConstructionComfort & Break-inDurabilityFit & Sizing
LEA
CON
❤️COM
🔧DUR
📐FIT
73
Points
63
Points

Score by Category

Leather Quality
100%100%
Construction
82%38%
Comfort & Break-in
43%89%
Durability
100%50%
Fit & Sizing
24%46%

Why is Bootmakers Trench Boot better than Stone Diesel Boot?

  • Better fit (46% vs 24%)
  • Better comfort (89% vs 43%)
  • Made in Chicago, IL
  • Horween Chromexcel leather
  • GYW construction
Based on 991 Reddit opinions
Too Close to Call

Reddit prefers the Diesel Boot

Winning by 4 points (77% vs 73%)

Better construction
Better durability
Better value
High confidence (991 mentions)

💬Reddit Sentiment

Based on 991 Reddit mentions

Overall Rating

Diesel Boot
7.7/10
690 mentions
Trench Boot
7.3/10
301 mentions
LEATHER QUALITY
Diesel Boot10.0/10
Trench Boot10.0/10
CONSTRUCTION
Diesel Boot8.2/10
Trench Boot3.8/10
DURABILITY
Diesel Boot10.0/10
Trench Boot5.0/10
COMFORT
Diesel Boot4.3/10
Trench Boot8.9/10
VALUE
Diesel Boot8.9/10
Trench Boot5.7/10
FIT
Diesel Boot2.4/10
Trench Boot4.6/10
⚔️

Head to Head

Head to Head

Diesel Boot: 3|Trench Boot: 2
Leather Quality
Diesel Boot100%
Trench Boot100%
ConstructionDiesel Boot
Diesel Boot82%
Trench Boot38%
DurabilityDiesel Boot
Diesel Boot100%
Trench Boot50%
ComfortTrench Boot
Diesel Boot43%
Trench Boot89%
ValueDiesel Boot
Diesel Boot89%
Trench Boot57%
FitTrench Boot
Diesel Boot24%
Trench Boot46%
Diesel Boot77%
Trench Boot73%
Close race - Diesel Boot edges ahead by 4 points

Key Specs

SpecGrant Stone Diesel BootOak Street Bootmakers Trench Boot
Last
Leo 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
Micro stud rubber outsole (also available with leather or wedge sole)
Dainite studded soles or other options

Key Highlights

Grant Stone Diesel BootWinner
🥾 Best price/performance ratio at $350
💰 Used pairs $175-$225
📏 Leo last: size down 0.5 from Brannock
⚠️ Insole glue may fail after 4+ years
👍 Storm Suede praised for ankle wrap
Oak Street Bootmakers Trench Boot
🇺🇸 Made in Chicago, IL
🎨 Horween Chromexcel leather
🪡 GYW construction
💰 $400-450 range
📏 Elston last runs TTS

Topic Battles

Diesel Boot: 2|Tied: 1|Trench Boot: 2
Leather Quality
Diesel Boot
100%
Trench Boot
100%
Construction
Diesel Boot wins
Diesel Boot
82%
Trench Boot
38%
❤️Comfort & Break-in
Trench Boot wins
Diesel Boot
43%
Trench Boot
89%
🔧Durability
Diesel Boot wins
Diesel Boot
100%
Trench Boot
50%
📐Fit & Sizing
Trench Boot wins
Diesel Boot
24%
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 Diesel Boot

Best Praise
+8 pts
I tried the diesel and loved it. I’ve stuck with them for dress boots and have 3 pair. No issues. Made pretty solid. The Dainite sole is slippery when wet and is rigid. I usually go for dainite but I think I’d rather have a leather sole. But I have 2 dainite soles. There are sales throughout the year. I hear their b-grades are a steal and nothing really wrong with them from what people have reported.
r/malefashionadvice
View
Top Criticism
+6 pts
That's not Grant Stone's Diesel boot, that's their Cap Toe Boot.
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
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

📈Historical Price Data

Grant Stone Diesel Boot
$280$320$360Nov '25Nov '25Nov '25Dec '25Dec '25Jan '26Feb '26Feb '26Feb '26Apr '26Low: $287.05Current: $334.95
Grant Stone Diesel Boot
All-time low: $154.95(2023-10)

Which is Better?

Grant Stone Diesel Boot Wins
77%
Boot
vs
73%
Boot

Close race, but Grant Stone Diesel Boot edges ahead by 4 points based on 991 Reddit opinions.

Why Diesel BootWinner
  • Better Value for Money (89% vs 57%)
  • More discussed (690 vs 301)
Why Trench Boot
  • 🇺🇸 Made in Chicago, IL
  • 🎨 Horween Chromexcel leather

❤️The Love/Hate Breakdown

Sentiment Breakdown

22%Positive
Positive
22%
Neutral
72%
Negative
6%
Based on 690 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 Diesel Boot or Oak Street Bootmakers Trench Boot?
Based on 991 Reddit comments, Grant Stone Diesel Boot has a slight edge with 77% positive sentiment vs Oak Street Bootmakers Trench Boot's 73%. The difference is small, so both are solid choices.
Should I buy Grant Stone Diesel Boot or Oak Street Bootmakers Trench Boot?
Both have similar approval ratings (77% vs 73%), so focus on specific features, pricing, and what matters most to you.
What do Redditors love about Grant Stone Diesel Boot?
Reddit users highlight: Best price/performance ratio at $350. Used pairs $175-$225. Leo last: size down 0.5 from Brannock. With 690 mentions and 77% 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 991 Reddit comments: 690 about Grant Stone Diesel 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.

282 Reddit opinions analyzed · Last updated 7/17/2026