Blundstone 500 vs Oak Street Bootmakers Trench Boot

103 facts in comparison

Based on 201 Reddit opinions. Close race—Blundstone 500 edges ahead.

201 opinions
Blundstone 500 leads by 3pts
Reddit's Pick
Blundstone 500
76%
B
Based on
241 Redditors
Winner

Blundstone 500

~$199.95
112 opinions

tldr; The everyday Chelsea. Slip-on convenience, decent durability. Not GYW but practical.

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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
67
Points
63
Points

Score by Category

Leather Quality
0%100%
Construction
50%38%
Comfort & Break-in
84%89%
Durability
82%50%
Fit & Sizing
50%46%

Why is Bootmakers Trench Boot better than Blundstone 500?

  • Made in Chicago, IL
  • Horween Chromexcel leather
  • GYW construction
Based on 542 Reddit opinions
Too Close to Call

Reddit prefers the Blundstone 500

Winning by 3 points (76% vs 73%)

Better durability
Better construction
Better value
High confidence (542 mentions)

💬Reddit Sentiment

Based on 542 Reddit mentions

Overall Rating

Blundstone 500
7.6/10
241 mentions
Trench Boot
7.3/10
301 mentions
COMFORT
Blundstone 5008.4/10
Trench Boot8.9/10
DURABILITY
Blundstone 5008.2/10
Trench Boot5.0/10
CONSTRUCTION
Blundstone 5005.0/10
Trench Boot3.8/10
VALUE
Blundstone 5007.1/10
Trench Boot5.7/10
LEATHER QUALITY
Blundstone 5000.0/10
Trench Boot10.0/10
FIT
Blundstone 5005.0/10
Trench Boot4.6/10
⚔️

Head to Head

Head to Head

Blundstone 500: 4|Trench Boot: 2
ComfortTrench Boot
Blundstone 50084%
Trench Boot89%
DurabilityBlundstone 500
Blundstone 50082%
Trench Boot50%
ConstructionBlundstone 500
Blundstone 50050%
Trench Boot38%
ValueBlundstone 500
Blundstone 50071%
Trench Boot57%
Leather QualityTrench Boot
Blundstone 5000%
Trench Boot100%
FitBlundstone 500
Blundstone 50050%
Trench Boot46%
Blundstone 50076%
Trench Boot73%
Close race - Blundstone 500 edges ahead by 3 points

Key Specs

SpecBlundstone 500Oak Street Bootmakers Trench Boot
Upper Material
Premium leather
Outsole
TPU outsole
Midsole
PU midsole
Lining
Unlined or partially lined
Calfskin vamp lining
Shock Absorption
SPS Max Comfort system

Key Highlights

Blundstone 500Winner
🇦🇺 Australian brand
👟 Slip-on ease
☔ Weather resistant
💰 Affordable
📦 Not resoleable
Oak Street Bootmakers Trench Boot
🇺🇸 Made in Chicago, IL
🎨 Horween Chromexcel leather
🪡 GYW construction
💰 $400-450 range
📏 Elston last runs TTS

Topic Battles

Blundstone 500: 3|Tied: 0|Trench Boot: 2
Leather Quality
Trench Boot wins
Blundstone 500
0%
Trench Boot
100%
Construction
Blundstone 500 wins
Blundstone 500
50%
Trench Boot
38%
❤️Comfort & Break-in
Trench Boot wins
Blundstone 500
84%
Trench Boot
89%
🔧Durability
Blundstone 500 wins
Blundstone 500
82%
Trench Boot
50%
📐Fit & Sizing
Blundstone 500 wins
Blundstone 500
50%
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 Blundstone 500

Best Praise
+43 pts
Blundstones with good insoles. You’d be hard pressed to find a better all-purpose shoe (yes, even for summer)
r/malefashionadvice
View
Top Criticism
+5 pts
My blundstones failed and they refused to replace them. My girlfriends failed in the exact same way and they replaced hers. I switched to redblacks, as they are better made and won't fail in the same way. Their service soured me.
r/malefashionadvice
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

Blundstone 500
$180$190$200$210Aug '25Aug '25Jan '26Mar '26May '26Low: $199.95
Blundstone 500
All-time low: $89(2017-05)

Which is Better?

Blundstone 500 Wins
76%
500
vs
73%
Boot

Close race, but Blundstone 500 edges ahead by 3 points based on 542 Reddit opinions.

Why Blundstone 500Winner
  • Better Value for Money (71% vs 57%)
Why Trench Boot
  • 🇺🇸 Made in Chicago, IL
  • 🎨 Horween Chromexcel leather

❤️The Love/Hate Breakdown

Sentiment Breakdown

36%Positive
Positive
36%
Neutral
53%
Negative
11%
Based on 241 Reddit opinions

Sentiment Breakdown

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

Frequently Asked Questions

Which is better, Blundstone 500 or Oak Street Bootmakers Trench Boot?
Based on 542 Reddit comments, Blundstone 500 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 Blundstone 500 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 Blundstone 500?
Reddit users highlight: Australian brand. Slip-on ease. Weather resistant. With 241 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 542 Reddit comments: 241 about Blundstone 500 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.

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