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Fashion Icon Michelle Obama Puts Spotlight on Chicago's 'Fresh' Conservatism

Washington Post fashion editor Robin Givhan says that Midwestern propriety, the city's history and the weather have shaped the fashion sense of the Windy City's residents.

On one of the coldest days of the year, one can't resist risking frostbite to wander the city and see if these folks can be stylish in below-freezing temperatures. Men wear dark overcoats and fedoras; a woman in a chestnut-colored fur stands out because of her metallic gold scarf, which looks handmade; and a stubbornly fashionable young woman in cropped black pants stands at a bus stop in snub-toed slingbacks and bare feet. But mostly, warmth trumps any slavish devotion to style.

Designer Cynthia Rowley, who grew up in Barrington, Ill., a northwest suburb, remembers the old wintertime image of "women in ankle-length fur coats with a matching hat. Furs were cool," she says. "No one was pouring paint on them."

"The joke is that my first collection, when I was still living in Chicago . . . was wool pants and turtlenecks in thick mohair. Sweaters and mittens. It was shearlings. A buyer said to me, 'Everywhere in the U.S. is not like Chicago.' It was totally like the frying-pan-over-the-head moment," says Rowley, now based in New York.

The brutal weather translates into a practical approach to fashion overall. "There's a total Midwestern sensibility. You're proud to have gotten a good deal," Rowley says. "It's totally counterintuitive to the whole fashion world where status and price makes something desirable, when in the Midwest it's that special thing you find, like a flea market find or the J. Crew outfit Michelle [Obama] wore on Leno."

While it is possible to find a man in an ankle-length mink trench coat on the Chicago streets these days, the women have long since moved on from that sort of matchy-matchy opulence. They have honed a style that is influenced by Midwestern propriety, the city's history and the challenges of the fashion industry as a whole.

Style matters here, but people aren't focused on adopting trends fast and furiously. And they don't save fashion for special occasions. Judith Byrd-Blaylock, a longtime Chicago resident before moving to New York four years ago, remembers being inspired to shun a bland corporate uniform as a freshly minted attorney in the 1980s. "I got my navy suit and white shirt, the women's version of the male uniform," she says. "Luckily, there was a woman partner who was very fashion forward. She was a role model. I didn't have to wear the uniform."

The Obama administration will include two high-profile women from Chicago who have been featured in Vogue magazine and celebrated for their everyday professional style: senior adviser Valerie Jarrett and Desiree Rogers, White House social secretary.

There are some 250 designers working in this city. Shopping is Chicago's No. 1 tourist activity, according to Melissa Gamble, who has been Mayor Richard Daley's point person on the city's fashion industry since 2005, and it has Neiman Marcus, Barneys New York, countless designer flagships and a fair number of high-end independent boutiques such as Blake and Ikram that help set the national fashion industry agenda.

"Chicago is not a fashion wasteland as people have come to regard the Midwest. It is very fashion conscious," Byrd-Blaylock says firmly. "They follow the fashion rules more closely. They ask themselves, 'How do we put that together in a way that is sophisticated and not too whimsical?' In New York and L.A. they're more focused on personal style and quirkiness."

When she lived in Chicago, Byrd-Blaylock traveled in the kind of social circle that included law firm events, charity galas and politics. She chaired the finance committee for Barack Obama's losing congressional race against Bobby Rush. She served on the finance committee for his U.S. Senate race and on his New York finance committee for the presidential one.

Chicago, she says, is a city dominated by business and civic institutions. "The way people dress generally reflects the culture of the community. When I think of Chicago, it's a big business community. It is culturally strong and growing, but it's different from a place like Los Angeles or New York," she says. "The attire is influenced by what is appropriate. You err on the side of being conservative. Sophistication above adventurousness."

'Pulled Together'

Michelle Obama reflects the Chicago approach to fashion -- albeit with a more enthusiastic embrace of color.

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