Photography: Clayton Hauck

George Vlagos

When George Vlagos, 31, was in middle school, his cobbler father deposited him unceremoniously in front of a pile of shoes at the family’s shoe-repair shop in the western suburbs, where he grew up. Vlagos spent all day shining them. “He was trying to scare me away from the business, but his plan backfired,” says Vlagos, who lives in Wicker Park. “I loved it. I started to ask myself, ‘Why can’t we make a shoe in America and offer it at a reasonable price?’ The answer was that we can.”

Vlagos launched Oak Street Bootmakers in August 2010 as an online shop, offering boots, loafers, and moccasins handmade by skilled artisans in Maine, many of whom once made shoes for Bass. The classic designs are made of leather tanned at the Horween Leather Company in Logan Square. Colors include deep browns and rich navy blues; prices range from $296 for the Trail Oxford to $426 for the Trench Boot.

Though the company doesn’t maintain a brick-and-mortar location, Vlagos owns the Gold Coast menswear store Independence, where he carries many of the shoes. The shop is also a great place to outfit the rest of your body, with LVC jeans, Gitman Vintage shirts, and American Optical sunglasses. 

Gitman Vintage oxford shirts

South2West8 canvas bags

Independence, 47 E. Oak St., 630-668-0867, and Oak Street Bootmakers.