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Oak Street Bootmakers

Brand Publisher · Dress shoes & boots · 10 mentions · 1 subreddit · discussed in r/goodyearwelt

Reddit take

Not enough linked mention summaries yet; the source excerpts below are the evidence.

Pros

  • I’m a big fan of OSB, mostly because they’re the only thing I’ve found that me perfectly (at least the Elston last)
  • I'd mention Oak Street Bootmakers if you want a slightly more modern styling to your loafters.
  • aside from the free shipping, I’ve also never been charged tax/import duties when they arrive here in the UK. Not sure if OSB is practicing the dark arts in that respect because it doesn’t seem to be added at checkout either.

Cons

  • It looks nice in photos but I'll never buy OSB again. Worst. Boot. Company.
  • Basically, I believe Oak Street had a bunch of B-stock/damaged boots that they tried to dump on sale without disclosing it. I'd steer clear of this company.
  • I’m not surprised from these practices from George. I mean the brand makes it look like they’re made in Chicago on Oak Street. ... They’ve never had transparency for their factories even when made in Batavia NY and whatever many Maine fa...
  • Curious what people's experience has been with quality from Oak Street Bootmakers. ... so was surprised that the pair I received had some markings / punctures to the leather finish on one of the boots.
  • Make: Oak Street Bootmakers ... Notes: New / unused. Thought these ran TTS but i think i need a 12 in these. Might be best suit for low volume 11.5 or maybe even an 11 brannock honestly.

Sentiment

3 positive (30%) · 3 mixed (30%) · 4 negative (40%)

Trust + time weighted score: -16% · raw score -10%

What redditors said (10 of 10)

It looks nice in photos but I'll never buy OSB again. Worst. Boot. Company.
negative · u/F****9 · r/goodyearwelt · comment · Nov 28, 2025 · open on Reddit ↗
Basically, I believe Oak Street had a bunch of B-stock/damaged boots that they tried to dump on sale without disclosing it. I'd steer clear of this company.
negative · u/S****o · r/goodyearwelt · Aug 13, 2025 · open on Reddit ↗
Basically, I believe Oak Street had a bunch of B-stock/damaged boots that they tried to dump on sale without disclosing it. I'd steer clear of this company.
negative · u/S****o · r/goodyearwelt · Aug 13, 2025 · open on Reddit ↗
I’m a big fan of OSB, mostly because they’re the only thing I’ve found that me perfectly (at least the Elston last)
positive · u/S****y · r/goodyearwelt · comment · Aug 12, 2025 · open on Reddit ↗
I’m not surprised from these practices from George. I mean the brand makes it look like they’re made in Chicago on Oak Street. ... They’ve never had transparency for their factories even when made in Batavia NY and whatever many Maine factories for their handsewns.
negative · u/B****n · r/goodyearwelt · comment · Aug 7, 2025 · open on Reddit ↗
I'd mention Oak Street Bootmakers if you want a slightly more modern styling to your loafters.
positive · u/o****6 · r/goodyearwelt · comment · Feb 18, 2025 · open on Reddit ↗
Curious what people's experience has been with quality from Oak Street Bootmakers. ... so was surprised that the pair I received had some markings / punctures to the leather finish on one of the boots.
mixed · u/M****a · r/goodyearwelt · comment · Feb 11, 2025 · open on Reddit ↗
Make: Oak Street Bootmakers ... Notes: New / unused. Thought these ran TTS but i think i need a 12 in these. Might be best suit for low volume 11.5 or maybe even an 11 brannock honestly.
mixed · u/R****0 · r/goodyearwelt · comment · Jan 22, 2025 · open on Reddit ↗
New / unused. Thought these ran TTS but i think i need a 12 in these. Might be best suit for low volume 11.5 or maybe even an 11 brannock honestly.
mixed · u/R****0 · r/goodyearwelt · comment · Jan 18, 2025 · open on Reddit ↗
aside from the free shipping, I’ve also never been charged tax/import duties when they arrive here in the UK. Not sure if OSB is practicing the dark arts in that respect because it doesn’t seem to be added at checkout either.
positive · u/B****h · r/goodyearwelt · comment · Jan 15, 2025 · open on Reddit ↗

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