“I think people tend to assume that because we’re Midwestern, we don’t care about clothes,” says Whitney Middleton, the mind behind Chance The Rapper’s iconic, ubiquitous overalls and Here Magazine’s issue 09 Jamila Woods cover shoot. “The vibe of Chicago is casual, but it’s still a look.” Middleton deals in looks—she made her name inventing the aesthetic personas of recording artists like Chance.
Chicago has been Middleton’s home base for the last thirteen years, and she credits the “magical” and “booming” city in part to her success. “I felt an instinctual calling that I needed to begin my work in Chicago,” she tells me. “That everything I was looking for and the dreams that I had could be realized here.”
Since the beginning, Middleton has had a particular affinity for vintage and secondhand clothing, and she knows Chicago’s vintage scene like the back of her hand—among some of Chicago’s other great amenities. See below for her stylist’s guide to the Windy City.
Woods. ”I’m incredibly grateful to have lived, worked, and created
in Chicago," she says. "The community is so special here—it’s a revolution.”
Whitney Middleton’s Perfect Day in Chicago
When I lived in Lincoln Square, I frequented Beans & Bagels for their incredible breakfast bagel sandwich (I got mine with eggs and veggie sausage). Nowadays, I go to Carver 47 Cafe in Hyde Park. Their smoothies are incredible, and all their profits benefit Little Black Pearl Academy.
I loved Virgil Abloh’s “Figures of Speech” at the Museum of Contemporary Art. Virgil is wonderful. I’ll never forget picking up a first-edition pair of Off-White x Air Jordan 1s from him for a shoot with Chance [The Rapper]—we met at a Red Line station for the exchange; totally casual. Support your local stars!
Also for art lovers: many of Chicago’s most impressive works of art lie in its architecture.
Brown Bag Seafood Co. is a real gem! I eat pescatarian, so it’s my spot for affordable fresh seafood served with heaping piles of veggies. They have Wi-Fi and plenty of comfy seating for hungry freelancers like me.
Vintage Shopping Gems:
My thrift abilities are a gift I love to share with special folks. I can’t give away all my secrets, but Family Tree Resale is a favorite, plus it’s just up the street from my go-to spiritual destination, The Chakra Shoppe. Their past-life regression therapy absolutely changed my present life.
I shop vintage and secondhand because it’s far more unique and eco-friendly than buying new, not to mention more economical. Knee Deep Vintage in the Pilsen neighborhood has amazing items from all eras, and their prices beat any fast-fashion store. For lovers of the 80s, 90s, and 2000s, there’s nostalgia galore at Kokorokoko Vintage in Wicker Park. And finally, don’t miss STORE. I’m such a fan of how STORE works with vintage and resale—they curate fantastic sellers in the chicest, most up-to-date ways.
I’m way into the mood of a classic Italian joint: dark wood interiors, cozy candlelight, mob vibes, and Sinatra, Sinatra, Sinatra. Hit Little Italy for The Rosebud and order the rigatoni alla vodka.
After the sun goes down, head to one of these eclectic spots for nightlife and music in Chicago.
Late Night Drinks:
You can’t beat the kitschy 70s lounge interiors at Heavy Feather in Logan Square. Bonus: Slippery Slope, the spot for sweaty dance parties on the nightly, is downstairs. Dance as long as you can, then scope out one of Chicago’s classic 24/7 diners like Jeri’s Grill. Order the Golden Brown Pancakes!
If you love musical theater and live music as much as I do, be sure to catch a show. Chicago’s theater district attracts big musicals and new productions alike. I’m partial to the Cadillac Palace Theater for its swoon-worthy interiors—plus, I love dressing up. Hit House of Blues, Thalia Hall, or Chop Shop for local and global music acts.
Photo by Clayton Hauck Thalia.
Where to Stay:
My first suggestion is to get away from downtown! I recommend staying at The Robey. It’s in Wicker Park, across the street from the Damen Blue Line stop, which can get you swiftly into the city if needed. There’s also a great strip of shops and restaurants on Milwaukee Avenue and North Avenue that are more local than touristy. Otherwise, explore AirBnb options—I like the Pilsen, Bridgeport, Hyde Park, and Logan Square neighborhoods.
Chicago Designers to Know:
I love Sheila Rashid—each piece is custom made to order. She’s famous for her overalls. If you’ve seen Chance The Rapper in overalls, you know her work! Denimcratic uses only recycled denim. I’m into the patchwork styles and founder Gabby Meyer’s radical take on denim. Legendary costume designer Michael Wesley White is the force behind Equitoria Couture. He has dressed icons like Chaka Khan and the Jackson Five. I recently teamed up with him to deconstruct classic menswear staples and turn them into a feminist statement for Jamila [Woods].