Countless celebrities have slapped their names on fashion lines, fragrances, or lifestyle brands—only to see them fizzle out in a season or two. Pop princess Jessica Simpson was not immune to the siren call of these celebrity business ventures.

While the world was laughing at this apparent “dumb blonde” for asking whether tuna was chicken or fish on reality TV, Jessica was quietly doing something most celebrities never manage: she was building a real business. A massive one.

And when I say “empire,” I’m not exaggerating. At its peak, The Jessica Simpson Collection generated more retail revenue than Michael Kors. It sold a dizzying array of products—shoes, handbags, clothing, fragrances—across 30+ categories, and appealed to women of all ages and styles. This wasn’t a vanity line. It was a billion-dollar machine.

Huzzah! Happy ending, right? Well… kind of. Jessica’s journey was just getting started. Because along the way, she lost control of her company. Then, against all odds—and using her own money—she fought to win it back.

Amy Sussman/Getty Images

Brand Origins

Back in the spring of 2005, Jessica Simpson was at the peak of her career. Actually, she was at the peak of her FIRST career. She may not have even realized it at the time, but she was actually at step one of what would eventually be a much more impressive and lucrative SECOND career as a retail mogul.

On March 30, 2005, Jessica’s three-season smash-hit reality show, “Newlyweds: Nick and Jessica,” aired its final episode. At the same time, she was putting the final touches on what would soon be a critically-acclaimed turn in the film reboot of “The Dukes of Hazzard.”

In the movie, Jessica took on the iconic role of Daisy Duke, which had been made famous by Catherine Bach on the 1970s/1980s TV show. Thanks largely to a poster of Catherine (as Daisy) wearing super short jean shorts that sold over 5 million prints, short denim shorts became forever re-named as “Daisy Dukes.”

As the film’s summer release date approached, Jessica and her mother/manager, Tina Simpson, began to take meetings with various merchandising companies to explore partnership offers to launch a Jessica Simpson retail business. The resulting business was called…

The Jessica Simpson Collection

The merchandising company Jessica and Tina chose to work with was the Camuto Group.

The Camuto Group was founded in 2001 by Vince Camuto. Vince earned his first major fortune as the co-founder of retail conglomerate Nine West, which he sold in 1999 for $900 million. In 2001, he launched the Camuto Group, which positioned itself as experts in manufacturing shoes for other brands.

For example, when Tory Burch, Lucky Brands, and BCBG wanted to launch a line of shoes without actually having to make shoes, they tapped the Camuto Group. When Tory Burch had a huge hit with a $200 flat (which was a quarter of the price of similar rival flats), they were manufactured by the Camuto Group.

Jessica and Tina were impressed with the Camuto Group and hit it off with Vince. So, a deal was struck where the Camuto Group would pay Jessica a fee to be the master licensee of her name on retail items. Vince also struck a side deal to acquire 25% of Jessica’s brand outright.

You might assume, considering the movie’s release, that the first product they made together was a line of Daisy Dukes, but Jessica actually wanted the first product to be a line of high-heeled cowboy boots. That’s partially why she wanted to work with Camuto specifically.

Jessica Simpson / Jamie McCarthy/Getty Images for QVC

Billion Dollar Brand

The high-heeled boot was a huge success, and the brand expanded fast – shoes, jeans, handbags, fragrances, swimwear, sunglasses, outerwear, lingerie, and more. Jessica, Tina, and Camuto worked closely to oversee licensing deals on products in more than 30 retail categories.

The brand struck gold by being accessible, stylish, and priced for middle America. No snobbery, just stuff women wanted to wear.

By 2010, the Collection was generating $750 million in annual sales. Four years later, it hit the billion-dollar mark. But in retail, revenue doesn’t always equal riches.

In 2014, when the brand generated over $1 billion, Jessica’s earnings were a meager $13 million. Just 1.3% of the gross.

(McCarthy/Getty Images for Jessica Simpson Collection)

Selling Out *** With A Brilliant Caveat***

Unfortunately, Vince Camuto died in January 2015 after a battle with cancer. That left Tina and Jessica feeling aimless and needing a new partner. So, in April of that year, Jessica sold 62% of the brand to a company called Sequential Brands for $117 million. Vince Camuto’s widow remained 25% owner, and Jessica continued to own a 12.5% stake.

With the sale, Jessica shrewdly included what would later prove to be an extremely brilliant deal point in her contract with Sequential. The contract required Sequential to give Jessica final approval rights over any potential acquirers if her brand was ever up for sale.

Sequential Bankruptcy

On the heels of their Jessica Simpson acquisition, Sequential went on a multi-billion-dollar debt-funded brand buying spree. That strategy was all well and good… until it wasn’t.

Here’s what happened to Sequential’s stock price as Wall Street soured on its acquisition strategy… and then as revenues were decimated by COVID:

Sequential filed for bankruptcy in February of 2021. At this point, the company, with a bankruptcy judge overseeing, began to seek offers for its various assets and brands.

Just as the vultures began circling, Jessica and her mom met with an investment bank to put together an offer of their own. An offer that would result in Jessica regaining 100% ownership of her brand, name, and license.

The Offer

Jessica’s offer consisted of $65 million in cash, mostly funded by Jessica PERSONALLY.

But here’s the best part – Jessica had a trump card in the negotiations.

Thanks to that deal point in her original contract, Jessica had the right to approve or deny any sale. That essentially made Jessica’s offer the only viable offer that Sequential could even consider!

Jessica’s offer was submitted in August 2021. In October 2021, the court approved Jessica’s offer. For the first time in her career, she owned 100% of her brand.

She marked the moment with a defiant Instagram post:

“I am truly humbled to reclaim 100% ownership of MY name and my brand… We beat all odds stacked against us… The entire Jessica Simpson Collection belongs to us!”

Even as Sequential was collapsing in 2020 and 2021, the Jessica Simpson Collection still managed to generate $500 million in gross retail sales in 2021. So it was far from a dying brand. While revenue figures for 2022, 2023, and 2024 haven’t been publicly disclosed, all signs suggest the brand continues to thrive. In April 2024, The Jessica Simpson Collection launched an exclusive collaboration with Walmart, rolling out a 100-item line across women’s and plus-size fashion, swimwear, and jewelry, most pieces priced under $30. The brand also remains widely available through major retailers like Dillard’s, Macy’s, Nordstrom Rack, and Amazon.

Neilson Barnard/Getty Images

What Happens Next?

I think the really interesting aspect of this story will happen over the coming years. Jessica previously earned just $13 million when her brand generated $1 billion in revenue. As 100% owner, she’ll get 100% of the profits from now on.

Let’s say she builds the brand back up to $1 billion in sales and maintains an industry-standard 20% profit margin. That would be $200 million in profits for Jessica every year. Considering how far she’s come so far, I wouldn’t bet against it!