Oak Street Bootmakers Trench Boot
Oak Street BootmakersRunner Up Best Boot

Trench Boot

$462

Beautiful boot with robust construction made in Chicago, featuring design simplicity that lets construction and materials speak for themselves.

Specifications

Type
service-boot
Material
horween leather
Sole
dainite
Construction
goodyear-welt
Made In
USA

Recommended by 4 experts

Expert Reviews

Reviewed by Stridewise, BootSpy, and Logan Kegley.

YouTubeStridewiseRunner Up Best Boot

Beautiful boot with robust construction made in Chicago, featuring design simplicity that lets construction and materials speak for themselves.

Pros
  • made in Chicago
  • Horween leather from Chicago
  • sturdy and versatile
  • resoluble
  • totally made in America
  • beautiful design simplicity
Cons
  • expensive at $462
  • not cheap for everyone
Watch the review
YouTubeStridewiseUnder $600

Super comfortable with nice wide toe, featuring highly skilled manual work like hand lasting that makes it a refined product.

Pros
  • super comfortable
  • nice wide toe
  • made in America
  • highly skilled manual work
  • hand lasting
  • refined product
Watch the review
YouTubeBootSpyRanked 9th - Least Worn

A fantastic, historically accurate WWI-style service boot with excellent Horween Chromexcel leather, but ranked lowest due to a wider toe box that doesn't suit the reviewer's preferences.

Pros
  • True to classic WWI/WWII service boot style
  • Horween Chromexcel rough out leather
  • Excellent leather quality
  • Great construction
Cons
  • Wider toe box
  • Lower wear frequency due to fit preference
Watch the review
YouTubeLogan KegleyBuy It For Life

Logan bought these in 2015 and still wears them as recently as a few days ago, praising them as a fully recraftable buy-it-for-life item that has aged beautifully and provided over 10 years of wear with minimal maintenance.

Pros
  • Over 10 years of wear with minimal maintenance
  • Only resoled once and replaced laces
  • Leather has aged beautifully from black to brown patina
  • Fully recraftable
  • Still available today in the $500 range
  • Cost-effective over time
Watch the review

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