The Secrets of Dressing Michelle

How are designers chosen to outfit the first lady? Rebecca Dana on the intense process that’s as mysterious as selecting a Supreme Court nominee. Plus, a gallery of Mrs. Obama’s style.

Michelle Obama calls fashion “fun.”

But for the legions of designers who dream of outfitting the first lady, she is serious business: powerful, potentially life-changing, and frightfully inscrutable.

Click the Image to View Our Gallery of Mrs. Obama's Style

When she emerged on Election Night in that sparkling red Narciso Rodriguez dress, Mrs. O looked to many in the fashion world like the second coming of Jackie O. But in the last 18 months, she has settled into a complex relationship with high-end designers, professing love, wearing their clothes lavishly, but also keeping her distance.

How does she choose her outfits? The process is akin to vetting a Cabinet member. A sleek bureaucracy separates designers from the first lady herself, filtering look-books, sketches and impassioned letters to her office and relaying, in return, only a personal check when an item is accepted for inclusion in her wardrobe.

As it has been since the campaign, styling the first lady is done entirely through Chicago-based, Israeli-born boutique owner Ikram Goldman, a towering, mysterious figure with slicked-back hair and a laser-sharp eye for couture. She picks out items that she judges will work for Mrs. Obama, making her selections at buying appointments with designers and from clicking through slides on, according to designers who have worked with her.

“I will never forget that moment for as long as I live,” designer Naeem Khan says. “ Your first lady wearing your dress.”

The press-averse Goldman, about whom designers speak as if she were a member of the Mossad, acts as the middleman in every transaction, buying clothes and then reselling them to Mrs. Obama, who cannot accept anything gratis. It is Goldman who gives notes to designers, fits garments on the first lady, chooses pieces from runway collections—and ultimately signs the checks. Does Mrs. Obama pay wholesale? Retail? “It’s best not to get into this,” said one designer who has outfitted the first lady. “It could get me into big trouble.”

Once selected by Goldman, designers are never told if or when their clothes will be worn and almost never come into contact with Mrs. Obama herself. (Repeated calls to the first lady’s press office and both calls and emails to Goldman’s Chicago boutique went unreturned.) One fashion publicist said the first lady’s office has a special phone line set up for designers wishing to submit clothes—but no one has ever answered when she called, and the voicemail box has always been full.

“It is a very long process and a very unsure process,” says Naeem Khan, the Indian-American designer who created the strapless gold dress Mrs. Obama wore for the first White House State Dinner. Khan, who credits that dress and the publicity that came with it for helping his business survive last year, was given five weeks to design a gown and almost no specifications. After rounds of sketches and feedback, Khan didn’t find out the first lady was wearing his dress until she appeared in it, on the receiving line that night.

“I was just getting ready for the night and watching television when I saw her walk out,” he says. “I will never forget that moment for as long as I live. It was the most exhilarating feeling. It was a top-of-the-world feeling. Your first lady wearing your dress.” Now, he says, people recognize him in the grocery store.

Khan has made a handful of other pieces for Mrs. Obama and hopes someday they’ll turn up on her “amazing shoulders.” But his is not a universal experience. Plenty of designers have had much less luck with the first lady’s Kremlin-like wardrobe department, getting only cold shoulders in response to their overtures.

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Oscar de la Renta, the American fashion titan who designs Hillary Clinton’s legendary pantsuits and has outfitted Nancy Reagan, Barbara Bush, and countless other women of substance and style, has yet to land one of his creations on Mrs. Obama. This may have something to do with a swipe he took at her last spring, after her visit with Queen Elizabeth. “You don’t go to Buckingham Palace in a sweater,” de la Renta said then. Just last week, he sounded a more wistful note, saying “I’d love to dress Mrs. Obama,” and admitting his “jealousy” of others who have.

De la Renta’s original gaffe hinted at the ambivalence some in the high-fashion community feel toward the first lady. Mrs. Obama plainly adores dressing up. She takes obvious delight in supporting young American designers like Jason Wu and Thakoon, and occasionally steps out in adventuresome pieces from edgier labels like Comme des Garcons. But she is also a populist figure in a prolonged economic downturn. She tills her own organic garden, busies herself fighting childhood obesity, and traipses with the girls back and forth from Air Force One in J. Crew cardigans and occasionally—shudder—capris. Her embrace of American sportswear has been sporadic and conditional. Not even an aggressive campaign led by Oprah Winfrey herself could get Mrs. Obama to turn out for last week’s Costume Institute Gala at the Met.

Some designers, including major domestic and international houses, have all but given up trying to dress the first lady. None would speak for the record out of dim hopes that someday maybe their time would come—or fear of winding up in de la Renta’s fashion purgatory. A few expressed frustrations with the inscrutable Goldman and with Mrs. Obama’s seeming prejudice against established figures like Donna Karan or Calvin Klein, in favor of young or niche designers. A few were critical of Mrs. Obama’s fashion missteps—those CdG cardigans, for example—and a developing sense of style, which Women’s Wear Daily, at pains to describe it, once called “more forced practicality than innate polish.”

Most took a Zen approach to the process. Back in 2008, Tommy Hilfiger was giving Mrs. Obama style advice. Today, his company is less gung-ho. “We do not have anyone working on dressing Mrs. Obama at this current time,” a publicist said.

Still, it’s hard to dismiss the appeal of dressing the first lady. For one, if you’re able to get Mrs. Obama to wear one of your dresses, the potential payoff is tremendous. Khan is now launching a cosmetics line that he plans to sell to India and recently completed a venture with the Home Shopping Network, which sold out its entire 2,500-dress run in 30 minutes—“all because of one dress.” Jason Wu’s chief financial adviser told The New York Times that the designer’s business has grown around 40 percent since Mrs. Obama wore his dress on inauguration night, in January 2009.

And for all the mystery, there is also a chance at some of that Mo-magic.

In March, Mrs. Obama donated the Wu inaugural dress to the Smithsonian. “I’ll never forget the moment that I slipped on this beautiful gown,” she told the crowd. “I remember how just luscious I felt as the president and I were announced onto the stage for the first of many dances. And I’ll cherish that moment for the rest of my life.”

No doubt the designer will, too.

Plus: Check out more of the latest entertainment, fashion, and culture coverage on Sexy Beast—photos, videos, features, and Tweets.

Rebecca Dana is a senior correspondent for The Daily Beast. A former editor and reporter for The Wall Street Journal, she has also written for The New York Times, The New York Observer, Rolling Stone, and Slate, among other publications.