Oak Street Bootmakers: Rebuilding the Footwear Landscape

By Gene Fowler

There are many steps in building a handmade shoe.

Longtime Chicago-area shoe repairman John Vlagos chuckles recalling his reaction upon first learning that his son, George, was starting the handmade footwear business, Oak Street Bootmakers. “I freaked out, you know,” says the father, with obvious pride in his son’s success.

Founded in 2010, Oak Street ships its trench boots, penny loafers, camp mocs and other styles—made in America from 100% American materials—all over the world. Its brick-and-mortar store, Independence, is a Chicago shopping destination. And when the Maine factory that made its products closed down, George bought the facility and all its equipment, saving some of the jobs of skilled American workers that have been moved overseas in droves.

The elder Vlagos, who immigrated to the United States from Greece in the 1960s, opened his suburban shoe repair shop on the day George was born in 1982. He’d wanted his son to go into a profession that didn’t require working with his hands. To teach young George the value—and the necessary determination—of hard work, John would take him to work on Saturdays, setting the boy in front of immense piles of shoes to be shined. But, instead of souring him on the business, it spurred him to later express a desire to someday take it over. “Absolutely not,” Pops decreed.

George Vlagos, founder of Oak Street Bootmakers checking in on production at the factory in Maine.

Honoring his father’s best intentions, George earned an M.A. from the University of Illinois and taught high school English for a time, but the appeal of fine footwear had worked its way into his blood. “I fell in love with shoemaking from watching my dad in his shop,” says George. “He would completely take apart and then remake a shoe, and that fascinated me. He would relast the uppers, rebuild the cork footbed and replace the welt, the midsole and the sole. And the customer would basically receive a new pair of shoes.”

As George grew older—and as more and more fine shoe and boot production moved to other countries, resulting in more American consumers buying cheaper footwear that was also produced overseas—he noticed that fewer well-made, longer-lasting items were being brought into his father’s shop. And that motivated him.

“There’s a rich legacy in American shoemaking,” he explains, “and Oak Street Bootmakers wants to preserve that heritage. I’m committed to helping to build back much of that footwear landscape that has disappeared.”

That disappearance also sparked the business in a more direct, personal way. “Around 2008 and 2009, I went shopping for a certain kind of boot,” George recalls. “It was clean and simple, my dream boot. But the design trend at the time was one of over-embellishment. I kept finding boots with skulls or crosses on them, which I didn’t want. So I designed and made my own, which became the prototype for our most popular boot, the Oak Street Trench Boot.”

While still teaching high school English, he designed and made more boots. “I thought I’d make a few boots to supplement my income, maybe sell 100 pairs a year. So on August 30, 2010, the Oak Street Bootmakers website went live. A friend’s blog post drove traffic to the site, and within 24 hours we’d sold out of everything. Then we inadvertently started selling shoes we didn’t have made yet, so instead of saying they were sold out we posted that everything was on pre-order. We found that if a customer was going to pay $300 – $400 for a pair of shoes, they were willing to wait six weeks for delivery. It was an amazing problem to have.”

Today, Oak Street Bootmakers offers some 69 varieties of footwear. Available through the company’s website, at its Chicago store, Independence, and Nordstrom stores, the line includes trench and chukka boots, bluchers, wingtips, oxfords, boat shoes, camp mocs and a variety of loafers — penny, beefroll, bit and tassel. There’s also the Camp, Summit and Lakeshore boots. Except for a handful of suede and calfskin products, all of Oak Street’s boots and shoes are made with the distinctive Chromexcel® leather, produced by the 114-year-old Horween Leather Company of Chicago.

Utilizing a formula developed by the Horween family 100 years ago, Chromexcel production takes 28 days to complete. It involves 89 separate processes, carried out on all five floors of the Horween facility. The proprietary Chromexcel recipe calls for food-grade beef tallow, cosmetic-grade beeswax, marine oil, chrome salts, tree bark extracts and natural pigments. Heated and steamed with this secret mixture, the resulting hide is durable and supple. Horween describes it as “the original pull-up leather” with “full aniline, hand-rubbed finishes.”

George says that natural Chromexcel is the most popular version. “It’s tanned and treated, but no color is applied. So, because every hide is different, every pair of boots or shoes will be different. Sometimes the natural trench boots will look darker on the website and a customer will ask if we shipped them the wrong color. So you do get lots of variation. But, it develops a beautiful patina. The natural Chromexcel shows how you’ve worn the boots or shoes more than any color can. It shows the character of the leather. People sometimes ask how they can expedite that patina more quickly. We always say, ‘Just wear ‘em.’”

And people are sure as heck doing just that. George’s Trench Boot designs remain the most popular, followed by the Beefroll Penny Loafer. “I also couldn’t find a beefroll penny loafer when I started the company in 2010,” adds George. “If you’re unfamiliar with the term, it’s a loafer with what looks like a little roll of beef placed on each side of the penny slot.” Close behind the Beefroll, the Camp Moc is Oak Street’s third biggest seller.

“That’s the shoe I wear the most, the Camp Moc,” continues George. “It’s a classic, iconic Maine shoe, really comfortable. I wear them all summer without socks, and then in the fall and winter I’ll add chunky wool socks. It really works across different styles and we’re one of the few American companies still making it. I have some from 2010 that I still wear – I’ve only resoled them once so far.”

Despite the hands-on, loving care with which Oak Street footwear is produced, George encourages customers not to walk on eggshells when wearing OSB gear. “We tell people not to baby the Trench Boots, for instance. You can even shovel snow in them. And when they need it, clean them with a wet cloth, apply Venetian Cream and then use a horsehair shoe brush on them. The first time you polish them, it really brings out the wear in a great way.”

One enthusiastic customer, Allen Farmelo of Buffalo, New York, took that advice to heart. “For the past seven years,” he testified in The Public, Western New York’s alt-weekly, “I’ve put my black Oak Street Trail Oxfords through hell. I walked thousands of miles in NYC in them, through slop outside Chinatown fish markets….over tarmac so hot that dogs have to wear booties. I’ve hiked Iceland’s lava fields in them, mowed the lawn, stacked wood, run a chainsaw….” And after all that, in addition to shining them for dinners out, he wore the shoes to his brother’s wedding.

Seeing them as a good investment, Alan purchased a pair of brown Oak Street Trail Oxfords with white soles and a pair of navy blue Oak Street Beefroll Penny Loafers. “I’m going to own these three pairs of shoes from Oak Street Bootmakers for the rest of my life,” he testified. “There’s a special feeling I have about that. I’ll call it kinship. I feel kinship to these specific pairs of shoes, but I also feel kinship with the American craftspeople and the manufacturing traditions that persist at Oak Street Bootmakers and Horween Leather Company.”

George Vlagos understands. “You feel a connection with the shoes,” he says. “You love ‘em. You sense the many hands that held the shoes as they were made. And, you know that you can have a profound effect through the decisions you make as a consumer.”

More and more consumers are making an Oak Street decision. The company’s business has grown by double digits every year. “It’s a great new adventure for younger customers. After saving up for their first pair, they’ll gradually build up their footwear wardrobe. And our older customers will often say, ‘I remember when shoes used to be made this way.’ I love hearing that.”


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