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Son reinvents family business, becomes shoe cobbler to the stars

Boot business finds success in going back to roots

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Oak Street Bootmakers

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Oak Street Bootmakers

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Oak Street Bootmakers makes no ordinary shoe. Heavy and velvety to the touch, their shoes are made of 100% genuine Horween leather and boasts Goodyear welted construction. And if you don’t know what that is, you're not alone – these used to be the standards of American shoe-making that are no longer. 

“We live in a disposable world where now you buy a pair of shoes, relatively inexpensively, and you wear them until they’re completely worn out and then you throw them out,” says Oak Street’s founder, George Vlagos. He describes his shoes as being made the old-fashioned way, using techniques that have disappeared from American shoe-making. “We really strive to create a product that you’re going to have forever,” says Vlgaos.

In more ways one, this boot business is a return to Vlagos’ roots: both the traditions of the craft itself, and also an unexpected return to his father’s family business.

John Vlagos, George’s father, is one of Chicago’s most beloved shoe cobblers, having owned and operated a shoe repair for over 30 years. John says he tried to instill a good work ethic in his son -- but at the same time admits to purposefully trying to scare him off, presenting young George with an impossibly large pile of shoes to polish on Saturdays in the hopes he’d dislike the task so much that he’d take advantage of all the opportunities that John says he never had for himself.

“I [didn’t] want George to work in the shoe repair, so I [pushed] him to work hard, get educated, do something nice, you know? Like a principal, or a lawyer if he wanted. He was a smart kid,” John says. 

Despite his father’s best efforts to scare him, “I really fell in love with it,” Vlagos says. Still, he went off to college and even taught high school English for a few years. But fond memories of his father’s shoe repair pulled at his mind. 

“One day I was out shopping for a very specific type of boot. And I thought to myself, ‘I’m not seeing beef-rolled penny loafers anymore, I’m not seeing shoes with a natural leather sole'. I wanted a simple, well-made brown leather boot, and couldn’t find it anywhere.” So instead, Vlagos resolved to make the shoes himself and did, using the skills he learned at his father’s shop.  “Very selfishly, I made that first boot for myself.  And almost immediately I realized that others will want this, too,” says Vlagos

After a financial investment from a friend, Vlagos reached out to a struggling factory in Maine who was about to shutter. “You had people there who had been hand sewing shoes their whole lives,” Vlagos says.

He paid some of the bills to keep the doors open and launched Oak Street’s website in August of 2010, the same day a fashion blog wrote them about their boots. From there, Vlagos says, “It spread like wildfire.” The company’s first run of inventory sold out within days of launching. There has been a six-week back-order period for new orders Vlagos has only recently caught up with.

With business booming, in 2012 the company opened a small retail shop on Chicago’s Oak Street, where musicians such as the Avett Brothers, Justin Townes Earle and Usher have all sung the company’s praises. Of course, celebrity fanfare also comes with a celebrity price: a pair will set you back over $400. Vlagos says shoppers should think of the shoes as an investment, which the company's repair policy reflects. Oak Street will re-craft any of their shoes at any time. Another option to extend the life of any well-made shoe for pennies on the dollar, as Vlagos suggests, "support your local cobbler!"

Of his son’s success, John boasts, “I’m very proud, yes! In the beginning he sold maybe one to two pairs of shoes a day, and now I see the trucks come and pick up shipments for Japan and international places.”  He adds, “He’s created a lot of work, a lot of good jobs,” referring to the company’s multi-million dollar business that now employs dozens of workers producing tens of thousands of hand-sewn shoes per year.  John is understandably one of George’s biggest critics, but even he can’t help gushing over the boots: “These are nice, handmade, American-made shoes.” 

Oak Street’s director of operations, Anthony Pace, adds: “[These two] are the American dream and I think of George as what can come out of that dream.” 

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Video produced by Sarah Lybrand; co-produced by Jessica Ashford & Emily Sharnhorst.  Production by Michael Manas, Richard Rella, Josh Kestner, Julien Griffen, and Maryann Vanderventer.  Edited by Sean Elms. Graphics by Todd Tanner and Adam Saul For Yahoo! Studios. Executive Producers: Russ Torres and Peter Gorenstein.

Special Thanks to: Horween Leather and Common Machine.

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