Jessica Simpson Reflects on 20 Years of Her Fashion Line, Date Night Outfits and More (Exclusive)

Twenty years ago, Jessica Simpson launched her fashion brand with a pair of classic red cowboy boots at 25 years old. “Some people didn’t think it would stand the test of time,” she tells PEOPLE in an exclusive interview reflecting on her legacy, “but I feel like everybody’s always thought that of me. One hit wonder…” 

Over 100 million pairs of shoes sold later, Simpson proved them wrong. 

Now celebrating 20 years, the Jessica Simpson Collection is still going strong, sold in over 20,000 retail locations. In addition to her signature cowboy boots, platforms, boho style tops, dresses and, yes, “Daisy Dukes,” (“There’s always a cut-off short,” she says) the line has grown to over 50 categories. 

“I feel like I’ve gone through so much,” says the singer, 45. “The brand has gone through the exact same things with me. Whether it’s babies or weight loss, we just wove it into the brand.”

In 2021, she and her mom, Tina Simpson, 65, bought back ownership of the brand from the parent company and reclaimed control. “We were the little engine that could,” she says.

Now separated from her husband of 10 years, former NFL player Eric Johnson (they announced their split in January) and ready to date again, the collection also has pieces for date night. Asked what she’d pull from the line, she laughs, “Well, hopefully things will be pulled off. Just kidding! A leopard-print dress, definitely heels, the Aaminas (her strappy platform sandals). I just called to get them in red,” she adds.

To celebrate 20 years, the brand dropped an exclusive limited-edition capsule collection out now on jessicasimpson.com and in select stores.  

“It’s a lot of celebratory pieces — just more me — like what I’d wear to the recording studio,” Simpson says of the “2.0” line featuring items like a bias leopard-print slip dress, platform sandals, furry bags and boots.

As she says, you can never go wrong with animal prints. “To me, leopard is neutral. It’s my beige,” she adds with a laugh. It’s a passion that was inspired early on by her maternal grandmother. “My nana, my mom’s mom, always had some form of leopard, a scarf or tortoise jewelry,” she recalls. “I just loved it. There’s even a Jessica Simpson suitcase in leopard. And I even have furniture that’s leopard.”

There’s a lot to celebrate, says the mom of three who shares three kids with Johnson, Maxwell, 13, Ace, 12, and Birdie, 6.

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“I was just in Pittsburgh to perform for the first time since 2008 for 60-plus minutes. It felt like home,” she says, “It was such an adrenaline rush. It was beautiful for me. I’m actually blessed to have gone through the hard stuff that I went through. I feel like I’m on the other side. I’m proud to be doing music independently and have my kids rooting for me. It’s more free than I’ve ever been.”