Billion Dollar Baby: Jessica Simpson Is Winning the Celebrity Fashion Game 10 Years In

When Jessica Simpson announced she was going to design shoes—10 years ago—in collaboration with Nine West cofounder Vince Camuto, no one thought much of it, including Simpson herself. She just wanted to make the kind of peep-toe platform heels she liked to wear with everything from maxi dresses to denim cutoffs. “I never thought I’d be some fashion mogul!,” she told New York magazine.

Today she is just that, with a fashion empire that’s still churning out those shoes (now they’re sold in 55 countries), plus her own Jessica Simpson-branded clothes, handbags, sunglasses, accessories, jewelry, fragrances, and more. It’s a $1 billion brand—and the company says it wants to double (or even triple) its revenue in the next decade.

At one point Jessica Simpson was best known for confusing chicken and tuna, an history-making error she made on the debut episode of Newlyweds: Nick and Jessica,  the reality show that chronicled her marriage to former boy band member, Nick Lachey. But that was back in 2003, and since then she has honed in on what seems to be her most successful and sustainable talent: Knowing—and green-lighting—the kinds of clothes, shoes, and bags that women actually want to buy.

Jessica Simpson with shoe mogul Vince Camuto at the MTV VMA’s in 2005. Photo: Getty Images.

In the wake of a decade’s worth of Jessica Simpson crochet tops, denim cutoffs, and floppy hats, it might seem like it’s easy for any celebrity to create a juggernaut fashion line, but Simpson is the exception, not the rule. In the aughts, anyone with a modicum of fame quickly created a namesake clothing brand, and most shuttered them just as quickly. Reality star Heidi Montag’s Heidiwood, with its zebra-print tops and micro shorts, lasted only a year. Remember Mandy Moore’s Mblem? The pop star—whose musical success is about equal to Simpson’s—debuted her contemporary knitwear and cashmere clothing the same year Simpson launched her line, but folded it three years later. “I love the fashion world. I’m fascinated by it. I’m humbled by it,” Moore told WWD during the aftermath.

What’s made Simpson stand out, in fact, is her willingness to not be humbled by fashion. She isn’t too bothered with what magazine editors or other tastemakers think of her clothes (or her for that matter). Her ambition isn’t to make the kind of fussy, once-a-season pieces that generate wait lists. It’s to create clothes that women will actually grab off the rack at Macy’s, Lord & Taylor, or Dillard’s whenever they’re looking for a stock-in-trade item that will make them feel good, like a flowing top or flared jeans— no matter their body shape.

“I have been every size on the planet, and I understand—I feel like I understand women,” Simpson said at Forbes’s annual Power Women’s Summit in 2014. “I know there’s all different kinds, you know. There’s life and a whole entire world beyond L.A. and New York. And I do understand the Middle America, and their mindset.”

Fashion cred, it turns out, does not make a celebrity designer successful. J.Lo is gushed over for wearing Versace and Zuhair Murad on the red carpet, but her Sweetface clothing line, which started out as urban streetwear before morphing—confusingly—into a contemporary line, lasted only six years (today, her JLO by Jennifer Lopez line is sold only outside the U.S., though she does have a line at Kohl’s). Lindsay Lohan’s legging-heavy wardrobe was once been heavily copied, but when she finally made her own line of leggings, called 6126, no one wanted to wear them. Or take Sarah Jessica Parker’s Bitten line, which was supposed to be affordable enough for, say, Carrie Bradshaw’s kid sister—it failed after two years (SJP now has a line of shoes and bags, SJP by Sarah Jessica Parker, sold exclusively at Nordstrom).

The only celebrity designers who’ve managed to equal Simpson’s empire are Ashley and Mary-Kate Olsen with their luxe basics for the Row and less expensive pieces for Elizabeth and James. Their business is also said to be worth at least a billion dollars, and the twins now consider themselves designers instead of actors. Notably, their names aren’t on their lines. “Listen, I used to be in the entertainment industry,” Ashley Olsen told the New York Times. “I decided at 18 that I don’t really want to do this anymore. I wanted to explore other things, and with that came The Row.”

Other successful labels include Gwen Stefani’s colorful, trendy L.A.M.B. and Victoria Beckham’s simple chic dresses, but their triumphs have been on a much smaller scale than Simpson’s.

The beginnings of Simpson’s fashion branding were humble—shoes, some clothes for tweens, a fragrance or two. Her business manager, David Levin, told WWD that the original idea was that, “a girl could go to the shopping mall with her mother and she’d have a great new outfit and still have some money left for lunch at McDonald’s. She can look like Jessica Simpson, smell like Jessica Simpson, and she can afford it.”

Today, Simpson and her mom, Tina, are still the heads of the brand and are, by all reports, very involved. “They are very thorough, down to looking at buttons and trim. They take pride in looking at products to make sure they exemplify Jessica’s ideas,” Jack Gross, the president of One Jeanswear Group, which makes Simpson’s denim and sportswear, told WWD.

In April, the brand got new backing from Sequential Brands Group, a licensing and management company, which bought a majority interest in the Jessica Simpson Collection and plans to make it even bigger by opening stores in America and beyond, and expanding the e-commerce and mobile commerce sales. But Simpson won’t be stepping back. “I’m as committed as I was 10 years ago,” she said when Sequential bought the brand. “Here’s to the next billion.”

Whether the Jessica Simpson brand can makes it to the next billion is still an unknown. Eric Beder, an analyst at Wunderlich Securities, cautioned in a note to clients that the company’s continuing to expand is a “wild card,” mostly because the brand is so focused on the American woman “in terms of sensibilities and color palette” that it might not be as appealing abroad.

Jessica Simpson models her own designs in her Spring 2015 campaign. 

It’s not as if other celebrities are leaving Simpson to own this world, either. The field is heating up again, in a way that’s reminiscent of a decade ago. Reese Witherspoon has Draper James, the clothing line that’s sold on her Southern lifestyle website, and seems to wear nothing but the line’s silk dresses, floral-patterned shorts, and lace tops since it launched.

In June, Kimora Lee Simmons relaunched her KLS label as a high-end line focused on working women: The cinched-waist and leather-accented dresses—and no velour jumpsuits—are sold at her new KLS boutique in Beverly Hills.

Adam Levine, too, has a recently launched womenswear line, which is sold exclusively at Kmart. “The best thing about designing a women’s collection is that I was able to create pieces that I would like to see a woman wear,” Levine said when it debuted.

Melissa McCarthy just debuted Melissa McCarthy Seven7, a collection that ranges in size from four to 28. And Eva Longoria, who says one of her hobbies is sewing, is launching a yet-to-be-named line in the fall, too.

Simpson, however, isn’t waiting around for the competition and continues to do her own thing: This spring, she’s putting out a line for infants. “A lot of people are afraid to listen [to their instinct] because a dream of [theirs] could be too big and it seems too big to attain,” Simpson told WWD. “I don’t believe any dream is too big.”

Follow us on Facebook, Instagram, and Pinterest for nonstop inspiration delivered fresh to your feed, every day.