When George Vlagos was in middle school, his father, a cobbler, would have him come into his Chicago shop to shine shoes every Saturday. John Vlagos, a Greek immigrant, was hoping to show his son that working with your hands is difficult and that he should get an education and find a different profession.
Well, it backfired.
Vlagos went away to school, studied English, and got a masters degree. But the jobs that made it possible for him to afford a pair of nice shoes ended up driving him back to the family craft when he realized how difficult it was to find a pair of quality shoes.
"I didn't think I had particularly crazy expectations," says Vlagos. "I wanted a shoe made in America, full grain leather, and at a reasonable price. I was really surprised that something that existed 20 to 30 years ago was disappearing."
Vlagos's father had also seen the shift at work on the shoes he was repairing, many of them made out of plastic that couldn't be resoled or with molded rubber soles that weren't repairable.
So Vlagos decided he would design the type of shoe he had been looking for. He found a shoemaker to hand sew his designs in Maine: According to Vlagos, the last part of the country where you can find craftsmen skilled in hand sewing. And he decided to source his leather in Chicago, where he is based, from Horween Leather Company, one of the oldest continuously operating tanneries in the United States. It's expensive, Vlagos says, but worth it. Since his company is small, he can visit Horween and select each hide himself.
On August 31, 2010, Vlagos launched Oak Street Bootmakers, without doing any marketing—and sold out of every shoe he had within 24 hours. Blogger and friend, James Wilson of Secret Forts, wrote a post about the launch of Oak Street boots, complete with multiple close-up shots of the details of a pair of trail oxfords.

"When I first Googled 'Oak Street Bootmakers,' nothing was online; our own website wouldn't even come up," Vlagos says. "Within 24 hours, websites in different languages were posting about Oak Street."
Vlagos was able to tap into two movements that were key to his success: The rising popularity of fashion blogs and a resurgance in American men's fashion that translated to consumers who are willing to pay more for high-quality goods. His designs are modern twists on classics, like boots, penny loafers, and boat shoes, featured in crisp, sleek photography on Oak Street's site. The vibe is chic, high-end Americana. Prices range from $210 to $356 for a pair.
"People will post photographs of themselves wearing their Oak Street shoes online. It's unbelievable," Vlagos said. "I don't have to get out there and say it myself. My customers will articulate it for me."
And Vlagos makes it a point to say "thank you," to customers. Everyone that ordered on that first day received a phone call. Vlagos takes pride in personally answering every email that comes in, too, sometimes surprising customers when they get one back at 2 a.m. And he inspects every pair of shoes and stamps the box as he packages them.
There's currently a six-week waiting list for a pair of Oak Street shoes. Vlagos's immediate goal: Have enough inventory to end the wait list, and slowly add more retailers as he grows production capacity. In addition to online, the shoes are sold in a handful of stores in London and New York.
Vlagos recently got a call from a store manager at Dunderdon, a store in the trendy Soho neighborhood of Manhattan, telling him that pop star Usher had recently bought a pair of his shoes. "The best part is as soon as he put them on he did a dance and said that he loved them," Vlagos said. "It blows my mind that people are walking the streets in New York, in Chicago, in other countries, wearing something that I designed."
And what does Vlagos's dad think about his son working in the business?
"He acts like he's still on the fence. He'll ask, 'Are you still selling them shoes?'" Vlagos said. "But if there's ever an opportunity to provide any support, he's the first person willing to help out."