Megan Weinerman at home in Lake View in her mutable As Four dress with suede Rochas pumps (right) and (left) cashmere turtleneck, John Galliano skirt, and Alexander McQueen boots

Megan Weinerman is touching the hem of her Alexander McQueen suede skirt. This is her favorite skirt, the one that men-even straight men-have told her is beautiful. The fabric is pale and butter-soft; the piece is from McQueen’s famous pirate collection, and if you look closely, you notice that it is torn in several places. “It’s not Megan-proof,” she says. “But what are you going to do? Keep it hermetically sealed? You have to wear it.”

Weinerman, a 38-year-old Chicago native, is untroubled by life’s imperfections, and her attitude is mirrored in the fearless way she approaches dressing in the morning. Passionate about designs by Commes des Garçons, Yohji Yamamoto, and Viktor & Rolf, Weinerman says, “I don’t follow trends much; what these guys come up with is so much more interesting.” Then, from her closet, she pulls a white Viktor & Rolf coat with flaps like a parachute. “I look like the Queen of Hearts when the wind blows.”

Does her fashion-forward style ever distract at work, where Weinerman is a freelance advertising copywriter? Not at all. “Pushing it is actually good in client meetings.” she says, “to show you understand image and identity.”

As for Weinerman’s identity, it is nothing if not playful, as indicated by her hilarious parody of the self-help genre,
I Love My Hair! (Weinerman has published three books with SimplyShe, a California company owned by her friend Maria Peevey.) At home, Weinerman finds inspiration in her own closet. Holding up a metallic cape by Nics
Andreas Taralis, she deadpans, “You have to be confident
in this one. “Otherwise it’s like, Am I Superman? What am I doing?”

We think she has it figured out.

WEINERMAN SAYS:

CAN’T LIVE WITHOUT “My Duro Olowu kimono dress, my Rochas tweed miniskirt with sequins, my Alexander McQueen buttermilk suede skirt with eyelets, my Comme des Garçons plaid and batik dress, my Rick Owens short-sleeved jacket-it goes on and on. And I haven’t even mentioned the shoes.”

IF YOU CAN’T AFFORD THE BLUE-CHIP BRANDS “I love the Chilean designer Zero [Maria Cornejo]. Her clothes are brilliant and affordable, and she doesn’t knock off the Japanese but creates her own structured style.”

BEST BARGAIN “Two coats I got from the Village Discount Outlet in Lake View a couple of years ago. I shopped there as a teenager and was very upset when it closed recently. Another good source is the Randolph Street market in the summer.”

ON COLLECTING “Once, after she witnessed my meltdown at a designer sale, my friend asked me if I was a fashion collector. But no,I don’t consider myself a collector, because I judge clothes by how much I love them and how I feel in them, not if they’re ‘important.'”

HER STYLE “I love a little glamour, a little drama, a little architecture, and a little pretty.”

PLAN AHEAD OR WAIT UNTIL THE LAST MINUTE “I always pick what I’m going to wear based on my mood that morning. But sometimes I’m being a chick and I can’t get dressed. You need to have things in your closet that you don’t have to think about.”

SHOPPING HEAVEN WOULD LOOK LIKE “Ikram and thrift/resale with a side dish of H&M.”

BEST ADVICE “The biggest mistake women make is thinking they look bad when they look great. My advice: Stand up straight, smile, and eat breakfast.”