Many layers – Chicago Reader

“Fall is such an enjoyable season, but short. So many options open up in the fall . . . layers, accessories, and outdoor wear. It’s brilliant to be outside in the cool crisp air, but still warm and comfortable,” wrote Schuyler Smith, 48. Smith, a design director at the architecture and design firm Studio Gang, emailed me after I photographed him on the street this fall. 

On that day, Smith gave cozy vibes while sporting a bright orange pair of clogs by Sven a shoe brand based in Minnesota. His footwear paired beautifully with his striped thrifted tee, Levi’s Japanese denim jacket, and Carhartt work pants. Smith described his styling process that day as the usual, “Wake up, try to get kids fed and dressed, and try to get myself dressed in the ten minutes I have before someone needs something.”

Despite his obvious fashion proficiency, Smith agrees with an eight-year-old who once described his style as “circus.” “I think that is close to accurate,” Smith admitted.

For inspiration, Smith looks to the women and girls in his life, concentrating specifically on real life. “I really don’t follow any social media. In fact, my advice on that is, don’t,” he suggested. “When following trends in an algorithmic environment, it is nearly impossible to see something new, outside your bubble.” Smith advocates that people look to a wide range of humans to get style ideas.

“It’s incredibly important to find out what you like, not what an algorithm says you are supposed to like,” Smith wrote. “Notice people in the physical world that are NOT of your gender, race, and age (but maybe have a similar body type).”

Speaking of body types, Jesse Fleming, 32, is a big fan of stylist David Kibbe’s body type system, established in his 1987 book David Kibbe’s Metamorphosis: Discover Your Image Identity and Dazzle as Only You Can, which she holds responsible for changing her whole style outlook. 

“Dress for your personality and your body, not for trends. Finding your Kibbe body type and your color season is a great starting point and makes shopping for clothes much easier,” said Fleming. “Anyone can find ways to look their best since personal style has no gender or size limitations, but your style speaks volumes before you even open your mouth—why not say something exciting?” 

Fleming also encourages people to lean into what they already own, avoid fast fashion, and buy secondhand and sustainable clothing whenever possible. “Ultimately this saves you money because it lasts longer, and you’re supporting small businesses and wage equality. Repair and rewear as much as you can,” she recommends. Fleming’s graphic printed coat by BCBGMAXAZRIA is one of her favorite pieces and only cost her $7 (purchased from online resale shop ThredUp). 

A freelance editor and the lead singer for rock band She Rose from the Dead, Fleming says she works mostly from home and doesn’t need a special occasion to sport her favorite looks. “I realized that if I waited for an occasion to put together a cute outfit, some clothes might never get worn again. Happily, that was not the case, but I still like to elevate everyday experiences,” she says. The day she was photographed, Fleming was making a humble Target run. “The right fall layers are really fun to break out year after year, and make me look forward to going out, even with the shortening days,” she adds.