Oak Street Bootmakers Trench Bootsearch

Oak Street Bootmakers Trench Boot

Oak Street Bootmakers Trench Boot

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Handcrafted in the USA

Built to last a lifetime, the Trench boot by Oak Street Bootmakers features a Horween Chromexcel upper, Goodyear-welt construction, stacked heel, and Oak Street’s Elston last. And this time around, we’re offering the boots in your choice of seven leather colors, including two new colors: brown waxed flesh and natural waxed flesh. Chromexcel is renowned for its smooth texture and durability, and it's hot-stuffed with waxes and tallows for deep, consistent colors.

Note: The Trench boot is here at its lowest price ever, available for this drop only. At checkout, choose black, brown, natural, no.8, or natural roughout Chromexcel (base price); or brown waxed flesh or natural waxed flesh (both + $15). All of these colors are available with a leather or Dainite (+ $30) sole and a plaintoe or captoe design. You can also add a cedar footwear care valet (+ $65). Oak Street Bootmakers recommends ordering true to size. These shoes are made to order and will ship approximately 7 to 9 weeks after the drop ends.

Oak Street Bootmakers Trench Boot

Goodyear Welt & Weather-Resistant Sole

Goodyear welting is among the best methods of shoe construction. This painstaking process can take up to 8 weeks to complete, but the rewards are many. For one, the shoes can be resoled time and time again. They’re also more resistant to water and provide better support than cemented or even Blake/Rapid shoes. For further protection against the elements, the leather outsoles are impregnated with oil, while the Dainite rubber soles are naturally waterproof. Inside, the Trench Boots feature a calfskin vamp lining.

Oak Street Bootmakers Trench Boot
Oak Street Bootmakers Trench Boot

Chicago Through & Through

Oak Street founder George Vlagos says the Trench Boots were designed to embody Chicago. Indeed, they’re designed by a Chicago-based company and made with Chicago-sourced Horween leather. But part of the boots’ Windy City appeal also lies in the company’s Elston last. Comfortable, durable, and unpretentious, with a well-rounded toe, the Elston last is designed for the everyman, the regular guy—the Chicagoan.

Oak Street Bootmakers Trench Boot

Shoe Cleaning & Shining Made Easy

Custom made for Oak Street Bootmakers, this footwear care valet is designed to add years—and even decades—to the life of your favorite footwear. Inside the cedar valet, you’ll find the Horween-recommended Venetian shoe cream, an American maple horsehair shoe brush, and a brushed twill buffing cloth. Also included are instructions for using the valet to keep your shoes looking their best.


Oak Street Bootmakers Trench Boot

  • Horween Chromexcel upper
  • Goodyear-welt construction
  • Stacked leather heel
  • Calfskin vamp lining
  • Leather sole: Vibram toplift
  • Dainite sole: Dainite toplift
  • Made in the USA

Optional Cedar Footwear Care Valet

  • Material: Cedar
  • Dimensions: 7 x 10 x 8.5 in (18 x 25 x 22 cm)
  • Made in the USA
  • Comes with: 3oz Venetian shoe cream, American maple horsehair shoe brush, brushed twill buffing cloth, and instructions


All orders will be shipped by Massdrop.

Estimated ship date is June 4, 2018 PT.

After the drop ends, payment will be collected and the group’s order will be submitted to the vendor up front, making all sales final. Check the discussion page for updates on your order.