Kristi
As a freelance hair and makeup artist, Kristi Wilczopolski lives and breathes fashion, so when the 25-year-old gets dressed, she likes to push the boundaries a bit. “I’m more of an accessorizer with shoes and jewelry,” she says. “I love oversized shirts that can be made into dresses.” Her style’s inspired by New York City’s Beacon’s Closet, AllSaints and Oak. “I like to test the waters a little with something really short and dramatic.”

Brad Richards, 42, is associate director of student and young alumni programming at the Wharton School at Penn. “I like to think of myself as modern prep. Being raised on the Main Line and going to an Ivy League school, a lot of my style is traditionally preppy,” he says. “But I like to update it and modernize it.” He’s a big fan of building diverse looks around an iconic item, like a pocket square or a good pair of brogues. “The best investment I ever made,” he says, “was a custom suit—it’s personal and traditional but incredibly flexible.”

Saad
“I love London street style,” says Saad Zain, a 22-year-old Drexel student who has lived in London, Kazakhstan and Dubai. “In East London, men wear a lot of floral shoes and plain jeans,” he says. “There’s such cheap stuff mixed in with expensive couture.” His own Ferragamos play off this style. “I’ve mixed it all in with the urban look of Philadelphia.” His advice: “You should only wear one thing with a label on it—keep it subtle.”

Alan
“My clothing inspiration is Peter Elliot,” says Alan Sandman, 67, a psychiatrist with Community Behavioral Health. He and his partner, John Pcsolar, have been together for 22 years and have traveled the world. “I buy much of my clothing in Buenos Aires and São Paulo,” he says, “because I’m a short fellow. It’s difficult to find shorter clothing in the U.S.” He also shops at Boyds, Distanté and Paul Stuart in New York. He’s had this vest from Brooks Brothers since he was a sophomore in high school.

Annemarie
“I’m a different person every day with my style,” says Annemarie Goffredo, 22. “I like to incorporate music into what I wear.” Classic rock and metal are on this Sisters bartender’s playlist these days, and her closet is filled with everything from skinny jeans and cropped jackets to torn stockings and band tees. “My style inspiration is also Rachel Zoe and my sister,” she says. “It’s risqué yet sophisticated. I like it dark and grungy.”

Ed
A freelance graphic designer and owner of his independent design company, Eddidit, for six years, Ed Hall, 31, is all about the details. “They may be little details that might not be noticeable at first,” he says, “but the more you look, the more you notice it, like stitching or a decoration.” He calls his style dressy street chic, and does most of his shopping online and at H&M and Topman. This vest is one of his favorite pieces. “It’s an asymmetrical dress vest with buttons that go across,” he says. “And hats—they’re new to me.”