Oak Street Bootmakers

Founded: 2010
Headquarters: Chicago, Illinois

Oak Street Bootmakers is an American footwear brand dedicated to preserving the heritage of fine U.S. shoemaking through thoughtfully designed and meticulously crafted boots and shoes. Founded in 2010 by George Vlagos, the son of a cobbler, Oak Street is rooted in a passion for quality construction and timeless aesthetics.

What began as Vlagos’s quest to create the perfect trench boot that he couldn’t find elsewhere blossomed into a brand committed to domestic manufacturing. All Oak Street footwear is proudly handcrafted in the United States using premium components like Horween leathers and Barbour welts.

The brand’s designs strike a balance between rugged and refined, blending classic silhouettes with modern versatility. From the signature Trench Boot to penny loafers and trail oxfords, each piece is built with an obsessive attention to detail and longevity through techniques like Goodyear welting and hand-lasting.

Oak Street embraces traditional shoemaking methods like hand-stitching and hand-bottoming, but innovates through proprietary features that enhance comfort and wearability. The use of partially-structured toes allows a natural break-in, while replaceable outsoles and the brand’s recrafting service enable each pair to be resoled and worn for decades.

By prioritizing skilled domestic labor and partnering with heritage suppliers, Oak Street Bootmakers is doing its part to ensure the continuation of quality American shoemaking for generations to come. As founder George Vlagos says, “We are the latest chapter in a very old story.”

Did you know? 
In addition to footwear, Oak Street produces its own line of American-made shoe care products and accessories like cedar shoehorns and lace keepers. Even the packaging utilizes domestic suppliers whenever possible.

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