Finding a Fashionopolis-worthy outfit is a lot less nerve wracking when you’ve got a $500 Mall of America gift card in your pocket and stylist Grant Whittaker, Fashionopolis producer, at your side. Meet Kelly Small, winner of our 2017 Road to Fashionopolis sweepstakes. She’s getting the royal treatment leading up to the big fashion show on Thursday. It started when Whittaker picked her up in a Bentley from Morrie’s and chauffeured her to the Mall of America (valet parking, of course). Their task? Find the perfect outfit to wear to Fashionopolis!
Whittaker didn’t have a difficult time styling Small—she already had an adorable boho vibe and a good sense of her fashion likes and dislikes. But she had no idea what to wear to an event like Fashionopolis.
“Wear something comfortable, since you’ll be sitting down,” Whittaker instructs. “But if you have something in your closet that you’ve never had the chance to wear, now’s your time.”
That could mean anything from bedazzled, distressed jeans to a fancy gown. The beauty of fashion shows: anything goes.
This fall, Whittaker is looking for clothes and accessories with unexpected details. At Free People, he steered Small toward a green patterned jumpsuit, then slung a shiny gold belt around her waist “for a Gucci vibe.” It worked.
He also picked up a navy floral H&M dress with a gathered tie around the neck, bright red skinny jeans—“I’m seeing a lot of red right now”—and a striped sundress.
“People forget about dresses at the end of the season,” he says. “But you could add a denim jacket, a scarf, and boots, and you’ve got yourself a cute little outfit.”
Small was drawn to a long sleeve floral minidress with sheer sleeves at Free People. Whittaker mentioned she could wear it on its own, or with sheer tights, leggings, or skinny jeans. The dress made her arms look even more toned than they already were, and her legs went on for miles. She looked comfortable, happy, and ready for Fashionopolis.

But wait—they weren’t about to leave the mall without hitting the Nordstrom shoe department. Long before meeting Whittaker, Small had been eying a pair of over-the-knee Stuart Weitzman boots. So long, in fact, that she had completely worn through the knockoff pair she bought instead of the real McCoys. They were still there, in flat and heeled versions. She gently tugged them on like a modern-day Cinderella, and immediately it was clear: These were way better than her old discount version.
Whittaker says the fall shoe trends are similar to clothing trends: full of unexpected colors, textures, and tiny details. Chunky heels are dotted with pearls and flats are adorned with pom-poms. They’re fun, like fashion should be. They follow Whittaker’s golden rule when it comes to fashion, and life in general: “Don’t take yourself so seriously!”
Small’s VIP treatment continues with beauty prep at Lili Salon Spa at Galleria and a chauffeured ride to Fashionopolis. Watch @mspmag on social media to see her final look!