When OSB‘s George Vlagos set out to create the Trench Boot, based off an old beat up pair of GI’s boots from the 40′s he’d picked up years before, it turned into a design process that would span five years, countless tweaks and modifications and plenty of wear testing. To hold just the right shape, and not satisfied with what was available, an entirely new last, the Elston, was created embodying the spirit of the Windy City and named after the street on which the citys’ own venerable, 107 year old Horween Leather is located. The result, two versions of The Trench Boot, a seriously handsome, seriously tough boot and like all OSB footwear, designed for longevity. After the jump, your first look at the all new Oak Street Bootmakers Trench Boot.

The Natural Trench Boot, $426: Natural Horween Chromexcel leather. True Goodyear Welt Construction. Oiled leather Waterlock soles(the soles are soaked in oil to prevent water from seeping in). Stacked leather heel with Vibram toplift. Calfskin vamp lining.

Vibram Sole Cap-Toe Trench Boot, $426: Natural Horween Chromexcel leather. Brogue Cap-Toe. True Goodyear Welt Construction. Vibram Cristy sole. Calfskin vamp lining.
And of course, both boots, like all Oak Street footwear, are fully recraftable and made in the good ole USofA(#duh).
Available today exclusively at Oak Street Bootmakers. Side note, if you’re in the Chicago vicinity, be sure to stop in to Independence. Where else but on Oak Street.
47 East Oak Street
Chicago, IL
(312) 675-2105

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  1. Jones says:

    Wow - 5 years in the making to make something that looks like Wolverine 1000 Miles, Alden Plain Toe boots, Dayton Service Boots, etc. etc. etc.! Very inspirational…

  2. David says:

    I think you’re missing the point Jones. Wolverine 1000 mile boots have a terrible toe and quite frankly, they’re Wolverine. Alden (while great) is pricier, Dayton service boots are made in Canada. Oak Street made a new last for these and it looks like much of that time was perfecting the last, studying the shortcomings of other boots, and making something far superior. I ordered mine and will have them soon! These will be my second Oak Streets!

  3. Mw says:

    Looks the same. Nothing new, nothing special.

  4. Brian says:

    the OSB’s are superior to those others, in material and design. top photo’s incredible.

  5. hai fucking win says:

    These mostly resemble the much costlier Viberg service boots with a soft toe. Your comparisons speak of your lack of attention or possible blindness, Jones.

    In any case, I ordered a pair.

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