The making of Jenna Lyons: How an election turned the J. Crew creative director into a household name

March 17, 2023, 12:33 PM UTC
Jenna Lyons, photographed during her tenure as creative director of J. Crew.
Andrew Francis Wallace—Toronto Star/Getty Images

Good morning, Broadsheet readers! Treasury Secretary Janet Yellen says the banks are sound after the SVB failure, Women’s World Cup players are competing for more money than last time, and Maggie Bullock, author of the new book The Kingdom of Prep, outlines the rise of Jenna Lyons at J. Crew. Have a relaxing weekend.

– Star power. On Oct. 27, 2008, even the most dedicated followers of fashion had never heard of Jenna Lyons. But that was about to change, and fast. Late that night, Lyons was at home in Brooklyn, in bed, watching the Tonight Show, when she suddenly jolted up. Michelle Obama had just walked onstage wearing a sparkly pencil skirt and jewel-studded cardigan, all in a mélange of yellow. This was the Jenna Lyons look—one she had created, as the creative director and president of J. Crew.

This moment was the first big spark in a star-making process that would catapult a woman who’d spent her whole career working her way up the ladder of a catalogue company known for preppy basics—hardly the glamorous end of the biz—onto the magazine covers, HBO guest spots, and red carpets of fashion’s A-list.

Today, Lyons is about to propel herself into our consciousness in a totally new way, as Bravo’s first openly queer “housewife” on a much-talked-about revamp of the Real Housewives of New York, set to debut this fall. Unlike most women who enter the Andy Cohen machine relatively anonymous and emerge on the other side famous, Lyons has already made a real mark on culture.

Jenna Lyons, photographed during her tenure as creative director of J. Crew.
Andrew Francis Wallace—Toronto Star/Getty Images

How did she become one of the most powerful and recognizable women in American fashion—and certainly the most famous ever to emerge from a mass brand, where her own name was never on the door? The rise of Jenna, a singular story in fashion, was due to an unlikely confluence of factors: an historic election; the rise of a blog culture newly obsessed with what was happening behind the curtain of the industry; and, perhaps most of all, a new era of female outspokenness that made Lyons exactly the right fashion star for her time.

The big idea inside of J. Crew was to scale up. The company wanted to be perceived as a sweet spot, somewhere between designer and mass. But in order to do that they had to convince people that these clothes were designed, considered, better than the competition—and therefore worth an elevated price tag. In order to land the message, they served up their secret weapon, Jenna Lyons—a woman who, with innate great style, could make J. Crew look like a fitting companion for Celine.

Lo and behold, Michelle Obama went on to wear J. Crew so regularly, it came to be referred to as the “house brand of the Obama White House.” In 2010, a Harvard Business Review article titled, “How This First Lady Moves Markets” would estimate that in a single year’s worth of appearances, Mrs. Obama racked up $2.7 billion in value for fashion companies—with J. Crew topping of the heap. For the first time, Americans could wear the same label as a First Lady. And they wanted to know about the woman who was driving that label. In an earlier White Houses, this would have been someone old world and regal, like Oscar de la Renta or James Galanos. Now, suddenly, it was Jenna Lyons.

In a fashion world that makes billions of dollars on the industry of “fixing” and concealing vulnerabilities, Jenna laid her own bare. Was it because she felt beholden to the lonely, awkward girls reading that issue of Vogue in their bedrooms, as Jenna herself had once done as an unhappy teen? Or was it because she simply didn’t know any other way to be? Either way, the Jenna-ness of Jenna was radical. And in a powerful one-two punch, she confessed these secrets while looking utterly confident—6”0 when barefoot, yet prone to heels; impossibly lithe; with a low-key way of putting together varsity-level looks. The flaws she talked about, you could not see. That mix of relatability and aspiration, polish and “realness”? You couldn’t put a dollar value on it.

Maggie Bullock is the author of The Kingdom of Prep: The Inside Story of the Rise and (Near) Fall of J.Crew, and co-creator of the cult women’s media newsletter, the Spread.

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