Oak Street Bootmakers

Doser: Oak Street Bootmakers

Founder: George Vlagos

Why we love him: Handcrafted in the U.S. using locally sourced Horween leather, Oak Street’s boots are the perfect kind of made-to-last shoes and boots for a Chicago winter.

Products: Hand-crafted boots, loafers, oxfords and boat shoes for the stylish man about town.

Dose appearances: October 16 and counting.