Whether they’re sitting front row or gracing our feeds, these Windy City style stars and their inspiring looks reign supreme.
WHO
As the Chief Strategy Officer of Zapwater Communications, lifelong Chicagoan Jennifer Lake (@jenniferlake) is a PR powerhouse—and she’s also made a major impact on the city’s style scene via her fashion blog, Style Charade (stylecharade.com), as well as her personal Instagram, both of which dive deep into fashion, luxury travel, home/interior design and lifestyle content.
BECAUSE
From fab flowing dresses to chic pantsuits and frilly pajamas, Lake’s style is feminine and flirty, colorful and vibrant, with patterns, stripes and textures galore–and we’re here for it.
SEEN WEARING
Carolina Herrera, KHOI, Loren Hope, Veronica Beard
WHO
Kathleen Haines-Finley is immersed in the world of luxury fashion and beauty every day. She has taught classes in fashion design for 28 years, first at the International Academy of Merchandising and Design, then Harper College, and since 2000 has worked at Neiman Marcus, where she’s now the business manager of Clé de Peau Beauté cosmetics.
BECAUSE
The current treasurer for the Costume Council of the Chicago History Museum, this Oak Forest and Crystal Lake native and woman about town knows her fashion history, citing Grace Kelly and Audrey Hepburn as her style icons, and her classically chic aesthetic always shines through.
SEEN WEARING
Valentino, Carolina Herrera, Oscar de la Renta, Christian Dior
WHO
With each putting his own artful stamp on installations across Chicago and the U.S., Nick Cave (@nickcaveart) and Bob Faust (@faust_____specialprojects) are one of the Windy City art scene’s premier power couples.
BECAUSE
No matter what the occasion, Cave and Faust are always on point when it comes to personal fashion—no wonder given that Cave is the creator of over-the-top wearable Soundsuits, which have been displayed all over the world.
SEEN WEARING
Nick explains, “I have a pretty extensive vintage collection, as well as many pieces I have made or modified myself and generally start there. Then I augment the rest of the look with what I am paying attention to in the moment. Right now, I am super interested in System and Chen Peng. Yohji Yamamoto is always in rotation.” Faust adds, “I watch a lot of designers and brands but look to each for different reasons. I love Jonathan Anderson for his creative brain. Rick Owens for casual bottoms. Gucci for footwear. And Hermès is always excellent, quiet and perfect. But I am super-excited by Willy Chavarria’s overall authentic vibe from his recent show. Ninety percent of my T-shirts are Nick Cave that I have accumulated over the past decade.”
WHO
With her eponymous unisex fashion line of colorful denim, jackets, shirts and accessories, Sheila Rashid (sheilarashid.com) is proving herself an influential force in Chicago style.
BECAUSE
Combining a tomboy look with a feminine touch, Rashid brings fierce fashion sense not just to her own line, but to her chic everyday looks as well.
SEEN WEARING
Rashid can be seen showing off her eponymous fashion line, of course, plus noted streetwear designers like BAPE (Rashid made sure to pop by the brand’s Oak Street opening last year).
WHO
Chicago-based dancer and visual artist Brendan Fernandes (brendanfernandes.ca) travels the world to present installations and performances of his art, and is becoming just as known for his sartorial style while doing so.
BECAUSE
Few Chicagoans wear clothing with such performative joy as Fernandes, who considers Isabella Blow, Iman and Jeanne Beker his fashion icons and who cheekily pushes boundaries at every turn, whether by pairing a perfectly tailored blazer with a skirt here, donning a wide mesh pant there, and delighting every fashionista in the crowd wherever he goes.
SEEN WEARING
Luar, Thom Browne, Comme des Garçons, Rick Owens, Richard Quinn, Todd Snyder
WHO
Chicago-based fashion designer Josh Kercher (joshkercher.com) has always believed that clothing is transformative. “It’s how we create the leading character in our own movie,” says the native of Grass Lake, Mich., surrounded by antiques, motorcycles and people who valued craftsmanship and taking care of what they owned has shaped the way he approaches style—fewer things, better things.
BECAUSE
Kercher always brings rock ‘n’ roll style to the table, and his passion for garments with a story—no surprise he’s a huge fan of thrifting during his travels—makes him stand out from the crowd. The latest fave of this West Loop resident, who cites sushi chef Jiri Ono of Jiri Dreams of Sushi as a style icon for his dedication to his craft and attention to detail: “Right now, I’m in love with our bespoke leather jacket program at KERCHER. There’s something so romantic about creating a piece that’s meant to last a lifetime.”
SEEN WEARING
KERCHER, Alessandro Vasini, Exoterix, custom jewelry by Ren Thompson
WHO
One thing you can count on with Cortney Hall: She is always camera-ready. As the Emmy-nominated host of NBC Chicago’s lifestyle show Chicago Today, she joins co-host Matthew Rodrigues in taking viewers on adventures around the city and suburbs, always with a megawatt smile.
BECAUSE
Whether dressed to the nines or in head-to-toe denim, you can count on the Oak Brook native—who also serves as an adjunct lecturer at Northwestern University’s Medill School of Journalism, where she earned her Master’s degree—to embrace her stylish side with playful looks and bold colors.
SEEN WEARING
Moschino, Azeeza, Alice & Olivia, vintage
WHO
Fashion insider extraordinaire Heiji Choy Black (@hejheij) has seen all sides of the industry, from owning hip boutique Hejfina to critiquing the scene as a fashion editor at Chicago magazine, leading chic brand Jeune Otte and now as head of VIP sales for jewelry line Almasika (almasika.com).
BECAUSE
Whether supporting beloved causes like the Art Institute and Uniting Voices Chicago or just stepping out on the town, Choy Black never puts a fashionable foot wrong.
SEEN WEARING
Raf Simons for Prada, Sacai, Almasika, Jonathan Anderson for Loewe
WHO
Unsatisfied with the quality and fit of suits available from designers or local tailors, Beijing native Ge Wang founded ESQ (esqclothing.com) in 2012; now he’s a go-to for professional athletes, celebs and power players alike with his bespoke line, which features fabrics sourced directly from top mills like Loro Piana.
BECAUSE
Dapper doesn’t begin to describe the style of this oft-suited, always-stylish custom clothier, who describes his style as casual, clean and refined and sets an impressively stylish scene in his Loop atelier—with a North Shore location set to open this spring.
SEEN WEARING
ESQ (of course), Canada Goose’s sustainable HUMANATURE collection, Rapha cycling gear
Photography by: JENNIFER LAKE PHOTO BY ALLIE PROVOST/PRÊT-À-PHOTO; KATHLEEN HAINES-FINLEY PHOTO BY MARK OLLEY; NICK CAVE BOB FAUST PHOTO BY MIKE VITELLI/BFA.COM; SHEILA PHOTO BY MATTHEW REEVES/BFA.COM; Brendan Fernandes PHOTO BY NEIL RASMUS/BFA.COM; JOSH KERCHER PHOTO BY JASON PETERSON; CORTNEY HALL PHOTO COURTESY OF CORTNEY HALL; BLACK HEIJI CHOY PHOTO BY HEATHER TALBERT; GE WANG PHOTO BY KEVIN PENCZAK
