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Kyle Middleton’s high school in Maryland had a clean-cut but bland dress code — khakis and collars, ties and Top-siders. It was way more conformist than creative.

Middleton ’15, though, is more about color than cookie cutter, and he likes to stir the pot a bit. As a teen, he snuck stripes onto the insides of his insoles and stood sideways to conceal cargo pants pockets from supervising eyes.

His style sense carried to the weekends, when he saw his friends still all dressed the same, just in the popular mall brands of the aughts instead of button-ups and belts. Wanting none of that, especially on his own time, he began shopping in thrift stores to stand out.

“To be different, I would thrift to find old-school jerseys, old-school Nike and FILA pieces,” he said, “brands that were still relevant, just pieces that weren’t in the stores because they were older.

“If there’s a trend, I love going against it,” he said.

When he got to ��«Ӱҵampa in 2011, it was often too warm to wear many of his coolest items. He had friends who were graduating and moving north, though, so soon Middleton was reselling to them his beloved and coveted team jackets and sweats. He also continued thrifting when he wasn’t going to his communication classes or basketball practice, and his reputation for having a good eye grew.

He started picking up women’s items, smaller and bigger sizes, and finds that made him think of specific friends. He created a group chat to send photos to about 15 people when he found fun, eclectic pieces. That group chat snowballed into an Instagram account focused on thrifted clothing.

After he graduated, Middleton worked full time selling New York Yankees Spring Training suites, cabanas and luxury boxes — and he kept accumulating thrifted inventory to sell online. By 2017, his one-bedroom apartment looked like a 700-square-foot closet. “It was about 80% filled with clothes, with maybe 20% living space,” he said.

It was time to get out of the house.

Middleton stuffed clothes in his car and, using his dog’s leash, strapped clothing racks to the roof to haul them to outdoor events like the Sustainable Spartan Market at ��«Ӱҵampa. Soon, business was doing well enough that he was able to go all-in on KY Vintage, which today has new a storefront at 3612 S. Dale Mabry Highway in South Tampa full of vintage T-shirts, team jerseys, denim, hoodies and shoes.

The best-sellers in the shop, he says are the tees, especially those from sports teams or with NASCAR prints. The shirts on the $5 dollar rack are especially popular. He keeps two racks of new items from local Tampa designers, too, to support their start-up brands and please potential customers who prefer that new-clothes smell.

If someone doesn’t see what they’re looking for on the floor, there’s a good chance he has something in the back (not in his apartment, anymore), that will be the perfect fit.

The shop is tucked into a small strip, easy to pass without noticing, so Middleton drives traffic from the KY Vintage social accounts. He and his one employee script, record and post four videos a day to promote the store and have some fun.

There’s more competition in the vintage shopping scene in Tampa these days, so when Middleton thinks about what’s next, he envisions a second store somewhere he can break into a market again, or maybe even back in the Washington, D.C., area, where his dream started. He’d hire managers to run both stores, so he could focus solely on his inspiration: the inventory.

“I want to help people to explore in their fashion, find their style and find something that's comfortable, affordable and accessible,” he said.

So in a way, his future lies in the past.