Family ties often bring Cynthia Rowley, husband Bill Powers, and their two children to the Windy City.

It’s an age-old question: How do you know when you’ve met the one? Well, in the case of fashion designer and Chicago-area native Cynthia Rowley and her art aficionado husband, Bill Powers, sometimes you don’t. “We first met in 1997 when I interviewed Cynthia for BlackBook magazine,” says Powers, who was editor-in-chief at the time. “Then we married other people. D’oh!”

The pair reconnected when Powers returned to New York from LA to be with his family in the aftermath of 9/11. And from there, “We did it all backwards,” says Rowley of their untraditional courtship. “We met, dated, had a baby, and bought a house. Then we went on a romantic honeymoonlike trip and he popped the question at the Taj Mahal. The very last thing we did was get married.” That’s not to say the wedding was anything short of spectacular: The couple wed in 2005 on the scenic cliffs behind artist Peter Beard’s Montauk, New York, home.

Since then they have been inspiring, supporting, and collaborating with each other in all of their artistic endeavors. On each episode of Bravo’s hit series Work of Art: The Next Great Artist (now in its second season), on which Powers is a judge, he lovingly sports a blazer from Rowley’s Mr. Powers men’s collection. When Rowley followed the models out onto the runway of her Spring 2012 show, she wore a T-shirt bearing the name of New York City’s Half Gallery, which Powers co-owns with Kate Spade cofounder (and the real Kate’s husband) Andy Spade and author James Frey.

While Powers, Rowley, and their two daughters have a permanent base in New York, thanks to two charming Cynthia Rowley boutiques in Chicago (in Bucktown and Lincoln Park) and Rowley’s parents’ home in Barrington (which she calls a “monument to my idyllic childhood”), the couple is in the Windy City often—most recently to attend her high school’s homecoming parade. “There’s always a good excuse for a visit,” Rowley says.

Now, six years married, Rowley and Powers live an artistic, outdoorsy, family-oriented life. And as far as artistic collaboration goes, it’s a constant discussion that happens between getting the girls ready for school, winding down for the night, and every activity in between. “Every day is a flurry of ideas about art, fashion, culture, family, and adventures,” Rowley says about life with Powers. “So the big question is always: Who gets first dibs?