What fashion stylist Katerina Kladis remembers most from her childhood in Chicago is the accessories. “I was always fully accessorized,” she says. “Matching shoes, bags, jewelry.” The daughter of Greek immigrants, Kladis became wholly obsessed with the subject. Today, the 33-year-old, who was recently featured in Vogue, has turned her obsession into a successful personal styling business. She’s unusual in the entrepreneurial world—a creative spirit who is also a savvy businesswoman.

For her clients, Kladis offers several fashion-focused services. She performs wardrobe assessments, style refreshes and closet clean-outs, plus personal shopping expeditions. One recent client needed a new wardrobe for an upcoming trip to Europe. Kladis chose three stores and pre-selected outfits at each location. She had the clothes waiting for her client to try on in the fitting room. Her client’s response? “I feel like Julia Roberts in Pretty Woman.”

When it comes to selecting outfits, Kladis tailors her choices to her clients’ styles. But in her own closet—well, it’s a different story. “It’s like a disco ball exploded in there,” she says, laughing. “I love a black dress, but I love wearing color too. Pinks, reds, metallics.” And she’s still a fan of accessorizing. “I can’t just wear a T-shirt. I need to wear rings. I need to wear earrings. I don’t feel like myself without them.”

Though her fashion sense has been influenced by popular culture, her business sense is a direct product of her parents. After they moved to Chicago from Greece, Kladis’ parents opened a string of thriving restaurants. “I grew up seeing how a successful business was run,” she says. “I got to see everything behind the scenes.”

When her parents moved to Southwest Florida several years ago, Kladis designed their restaurants in Naples and Fort Myers. She also worked the front of the house. Not surprisingly, that was her favorite spot. “I love working in the front and talking to people,” she says. “It made me so happy.”  

Hot tip: Always reach out

Though Kladis could point to several reasons for her entrepreneurial success—her charm, her good taste, her willingness to put in the work—the No. 1 factor in her rise has been her ability to make connections. “Any way you can, just get your name out there,”
she counsels.