New fashions from Maria Pinto. For more photos, see the photo gallery.  Photography: Courtesy of Fashion Focus

In 2006, Mayor Richard Daley announced that he was putting more money and clout behind the city’s fragmented fashion scene. After all, he had done the same for the restaurant business, and it had bloomed. Boosting fashion would enliven the city’s 2016 Olympic bid, too. So he appointed a new city fashion director and named an advisory fashion council.

National press took note—with one eyebrow raised. In June 2006, Time asked, “Can Chicago become a fashion capital?” noting that our town is known more for its frigid winters, fine architecture, and hapless Cubs than high fashion. Undeterred, the city moved forward and, from virtually nothing, produced a week of runway shows that September in Millennium Park. For at least one night, during a Macy’s event that spotlighted some of the city’s most respected designers, the energy and optimism were palpable. “There was a certain excitement,” says the designer Orlando Espinoza, a former cochair of the Mayor’s Fashion Council. “Before, everyone was in their own world. The walls were no longer there.”

Flash-forward two years. As the  black-clad, stiletto-enhanced crowd filed out of the last show of fashion week this past fall, the rainy evening seemed almost anticlimactic. After the finale—an eco-friendly segment from Organik Revolution, the night’s highlight—members of the local fashion press seemed to look at one another somewhat nonplused, as if to say, “Okay, I guess that was it.”

For despite posting record attendance (on average, 1,200 people per show) and improving its sophistication and scope (adding industry seminars, an all-student fashion show, and shopping events), the city’s fashion week, which is called Fashion Focus, has become, more than anything, a lively social event. As organizers spend the next few months plotting the initiative’s future, designers Chicago spoke to are calling for more industry oomph and ways to stimulate commerce. “I think we need to re-evaluate Fashion Focus, period,” said Nick Cave, a member of the fashion council and former chairman of the fashion department at the School of the Art Institute.

Espinoza, who did not participate in Fashion Focus in 2008 and has since stepped down from his position on the advisory council, agrees that Chicago’s fashion week needs a makeover. “You need to see progress or it just becomes the same thing year after year,” he says. He adds that he and other designers were disappointed by the lack of buyers, high-end clients, and press. “There was no business that transpired,” he says. “The press was more intrigued by who was attending than who was showing.”

In all fairness, organizers are providing a showcase for designers, most of whom would have no other forum, and have helped unite and elevate an underdog scene. “People in the industry are taking us more seriously,” says Melissa Gamble, the city’s director for fashion arts and events. Hearing her title, “people used to say, ‘You’re doing what?’ with a smirk on their face,” she says. “I don’t encounter that at all now. Before, people didn’t realize there was fashion here.” She adds that a few new designers, such as Kate Coxworth, the name behind the tailored-shirt line Kate Boggiano, have moved to the city based on its growing reputation.

But keeping fashion folk happy and engaged is a difficult task. They expect excitement, innovation, and newness. They’re notoriously fickle, not to mention critical, since the industry is, after all, based on constant change. The city knows this, and recently commissioned a study, conducted pro bono by A. T. Kearney, that will detail where the city’s fashion and retail business ranks in relation to, say, Berlin, New York, and Los Angeles. (Its findings are expected to be published in the first quarter of this year.) “The question we need to answer is—what is the next step?” said Jason Felger, cochairman of the Mayor’s Fashion Council and executive vice president of the Chicagoland Entrepreneurial Center. Several designers and industry insiders to whom Chicago spoke were ready to offer up their own suggestions on how the city could freshen its direction, including:

Cave’s solution is simple. Condense the lengthy eight-day fest into a three-day weekend with individual designers or teams of designers staging their own shows throughout the morning and afternoon, a format similar to New York’s Fashion Week. Spread seminars and shopping events in between. The city’s larger, more inclusive runway events could be staged at night. “It creates a saturation of intensity,” Cave says.

Since Fashion Focus’s inception, only a handful of local retailers have attended (though more turned out last fall). That’s troublesome if Chicago truly wants to keep designers from fleeing to New York or Los Angeles.

Although Gamble knows buyers are a critical piece of the puzzle, the city has yet to put significant resources or effort behind such outreach. “We know buyers are crucial,” she says. “We’re recognizing that it’s a need, but it’s a funding issue.” (In 2008, Chicago budgeted $225,000 for Fashion Focus, an event that costs upward of $600,000, with the majority of funding coming from sponsors such as Toyota and Lancôme.)

Buyers by the hundreds already travel to Chicago each October for Style-max, the Midwest’s largest women’s apparel market, held at the Merchandise Mart. There, retailers from around the region, from Nordstrom to Cinnamon Boutique in Roscoe Village, place orders for Three Dots T-shirts and dresses from BCBG for next season. Designers ask: Wouldn’t it make sense for Fashion Focus and Stylemax, which is held quarterly, to coincide?

The designer Pierre Colorado, who has built his Chicago-based brand Blake Standard into an almost $2-million business, said many of the emerging designers need help turning their artistic pursuits into a business. “It’s a tough industry to begin with,” says Colorado, whose clothes are sold at 250 stores around the world. “There’s so much—the backroom particulars—not presented to [young designers].” For example, he points out that some retailers have strict shipping guidelines, including the size of the box, the size of the hanger, and what day to ship. He also proposes offering emerging designers an educated, real-world critique. Take a local label with a dress priced at $500. “It may be pretty, but at that price, you’re competing with the biggest names from Paris and Milan,” he says. “Someone needs to say, ‘Are you sure about that?’”