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When does the first lady’s style turn into success for the designer behind the dress?

best foot forward Michelle Obama is revered for putting designers on the radar, but not all of them score a direct hit, like Maria Pinto, whose dress Obama’s wearing here.

The adage “luck is what happens when preparation meets opportunity” is especially true for the fashion designers whose outfits have graced a first lady’s figure. Perhaps that’s why some (Jason Wu, anyone?) have flourished, while others (Remember Sarah Phillips? No?) flopped.

Wu and Phillips, the inaugural ball gown designers for Michelle Obama and Hillary Clinton, crystallize that distinction. Their stories also illustrate how Obama, more than any other first lady, has acquired a Midas-like touch for fashion, akin to Johnny Carson’s ability to catapult comedians into the national limelight.

Unlike former fashionistas Jackie Kennedy and Nancy Reagan, who dressed with Hollywood flair—and budgets—Obama is the first populist style icon to occupy the White House, filling her closet with designers that appeal to women on every budget. “Michelle Obama changed the course of fashion history the moment she combined Isabel Toledo with J.Crew on the day of the swearing-in ceremony,” says Lauren A. Rothman, stylist and owner of the fashion-consulting firm Styleauteur.

Wu boarded the publicity train the moment Obama stepped onto the dance floor that evening. He told Atlantic Media scion Justin Smith’s that he did more press in the two days after the inauguration than in his entire career. Combine his quick response with the close proximity to the fall 2009 New York Fashion Week, and it’s not much of a surprise that Target launched his eponymous line soon after. The rest, as they say, is history.

Rewind further to 1993, and the landscape couldn’t have been more different for Sarah Phillips, as she watched Clinton emerge at the balls wearing Phillips’ violet lace-and-mousseline gown. Why haven’t most of us heard of her? Poor timing. “I had a request for the Academy Awards, but became pregnant and was not set up to handle a huge business,” Phillips says. Yet, even if she hit the red carpet running, the probability of reaching the heights of Wu stardom would have been unlikely.

“It’s no longer enough to be a great designer. You have to be dressing a fashion icon,” Rothman says. “Hillary Clinton just didn’t own the fashion sector. It’s just not who she is.” Not to mention the fact that the Internet was still mostly the domain of university labs, so Phillips never got a chance to go viral with the fashion masses.

But the designer is back from a 20-year hiatus, re-launching with an atelier-style approach. While her dress lives in the Smithsonian National Museum of American History, her new evening coat-focused collection is finally available online ( and to private clients who can customize styles with fabrics like wool satin or pure cashmere. “Creating the inauguration gown was a wonderful gift,” says Phillips. “Yet, it didn’t dictate the rest of my career.”

And Phillips isn’t the only one whose historical fashion moment is a footnote, rather than a foreword. Even though Obama’s frocks hit the blogosphere the minute she steps out the door, not every designer she’s worn has translated the hit into a booming business. Maria Pinto opened her own boutique in Chicago in 2008 after Obama was frequently spotted wearing Pinto’s shift dresses on the campaign trail. The publicity got her noticed on the pages of Vanity Fair, Vogue and People, yet the shop closed two years later.

Perhaps the recession played a role, but the answer may simply lie in the grandeur of the events where Obama chose to wear her designs—the first lady relies on Pinto for affairs that tout sophistication, rather than the fanfare required of an inaugural ball. Obama’s loyalty to Pinto—she continues to wear designs purchased before the stores’ shuttering—may be why the designer is not jumping through hoops for more attention. She’s pouring her creativity into other projects instead, such as the current exhibit Fashion and The Field Museum Collection: Maria Pinto through June 16 in Chicago.

Toledo, on the other hand, is still riding the elevator to stardom that commenced with the overwhelming response to her lemongrass wool guipure overcoat and dress that Obama wore to her husband’s swearing-in. Like Wu with the ball gown, Toledo’s design led to collections for mass-market retailers and a memoir, Roots of Style.

Just last month, she and her husband, Ruben, opened a retrospective in the Freedom Tower at Miami Dade College Museum of Art + Design with a room dedicated to the first lady—“the first lady’s armoire,” as Toledo calls it. Still, Toledo is careful about inflating her business too quickly. “She hasn’t let it go to her head,” Rothman says. “She is still very grounded from a business perspective; that is what investors want to see.”

The fashion lens is already trained on the White House for January’s inaugural events, providing the chance for whomever Obama wears to kick-start their business, or simply fizzle. “Anyone can get on Project Runway or have a collection for a pop of a second, but it’s not enough,” Rothman says. “Success is a three-point strategy. You must have good design, attain visibility and secure accessibility through a retailer.”