
Stepping out of the building that hosts performance spaces Links Hall and Constellation on a chilly spring Friday night, theater consultant Cydney Patrice Cleveland turned heads in an unexpected yet cohesive mix of leopard overalls, a military-style jacket, pearls, fringed ankle boots, and an African print clutch.
“I like to shop small and thrift to find things that make me smile,” she said. “The jacket is from Romeo and Juliet Couture, the leopard print jumpsuit is from Amazon, shoes are a thrift find, and clutch is from a [pop-up market] supporting Okodwela,” a charitable organization that helps build homes in rural areas in African countries.

For 38-year-old Cleveland, it’s go big or go home. “I love fashion and expressing myself big and boldly,” she said. Her style is very authentic to herself, so much so that she can look back on her wardrobe without major regrets. “I’ve been working on my closet since high school. Yes, I can still wear and have pieces from 20 years ago,” she said.
Cleveland is not plagued by the “full closet but nothing to wear” syndrome that affects some of us and she thinks that “clothes are meant to be worn.” Every day presents an opportunity for her creative combinations, chosen according to her mood. “I feel like there are no special occasions,” she said.
Cleveland was feeling “a little dark and moody” on the evening she was photographed, after enjoying the work of artists Jacinda Bullie and Jaquanda Villegas from “my Kuumba Lynx family.”
“I’m currently consulting on [Kuumba Lynx’s] new dance and healing [center] in Uptown with Lady Sol. Ribbon cutting on May 17 at 4755 N. Sheridan,” she said. Cleveland should be wearing something remarkable for the occasion, since for her, “style means how you wanna show up for yourself.” To achieve such impressive outfits, she recommends people “wear their clothes and play with them.”

“Try something different or new. You won’t know how it looks or makes you feel until you try. And at the store, try on different silhouettes. You’re already naked, so try on something different—you might surprise yourself.” Cleveland also encourages folks to go out and support the arts.