If you grew up in the early 2000s, you remember the Simpson sisters as the twin pillars of MTV’s golden era of reality TV. Jessica was the "Chicken of the Sea" blonde who turned a ditzy moment into a billion-dollar fashion empire. Ashlee was the edgy, black-haired younger sister who gave us the pop-punk anthem of our teenage angst. But look at them now. In 2026, the narrative surrounding Jessica Simpson and her sister Ashlee has shifted from tabloid rivalry to a masterclass in sisterly survival.
Honestly, it’s rare to see famous siblings stay this tight. Most Hollywood families implode under the weight of "who’s more famous." Not these two. Right now, as Jessica navigates a high-profile separation from Eric Johnson and Ashlee experiences a massive career renaissance in Las Vegas, their bond is basically the only thing that hasn't changed. They’re still each other’s "ride or die," just with more kids and much better business managers.
The Las Vegas "Resurrection" and Supporting the Family
Last September, the sisters made headlines for more than just their outfits. Ashlee kicked off her "I Am Me" residency at Voltaire at The Venetian Resort. It wasn't just a nostalgic trip through her 2005 hits; it was a full-blown comeback. Jessica was right there in the front row, crying her eyes out.
"I was a mess," Jessica told reporters later. "I cried probably seven times."
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That’s the thing about Jessica Simpson and Ashlee Simpson. They don't just show up for the cameras. Jessica attended that show alongside her estranged husband, Eric Johnson, proving that "family first" isn't just a hashtag for them. They’ve managed to keep their private lives relatively sane despite the public split Jessica announced in January 2025. By early 2026, the two have been seen coordinating holiday events and birthdays, emphasizing a united front for their six combined children.
Why Ashlee is Winning 2026
While Jessica has been the business mogul for two decades, 2026 is arguably Ashlee’s year to shine musically.
- The Residency: Her "I Am Me" show was so successful it was extended with new dates in late January 2026.
- The Sound: She’s finally embracing the 2000s "angsty pop" that her fans never actually stopped loving.
- The Balance: Living in Las Vegas allows her to maintain a semi-normal life with her husband, Evan Ross, while still being a headliner.
Music Collabs and the "Nashville Canyon" Era
For years, fans have begged for a Simpson sister duet. It feels like a missed opportunity from 2004, doesn't it? Well, we might finally get it. During an appearance on The Jennifer Hudson Show late last year, Jessica dropped a major hint. She and Ashlee have been talking—really talking—about a collaboration.
This isn't just about them, though. Jessica mentioned that their kids are "musically inclined" and could be part of the project. Imagine a track featuring Maxwell’s perfect pitch and Birdie’s "belting" power alongside their moms.
Jessica’s own musical journey has been a bit of a roller coaster lately. She released her Nashville Canyon EPs in 2025, her first original music in nearly 17 years. It was a vulnerable, "genreless" project born out of her heartbreak and her journey through eight years of sobriety. She’s no longer chasing the #1 spot on the Billboard Hot 100; she’s just making music that feels like her. And Ashlee has been her biggest cheerleader through that entire "resurrection" process.
Reclaiming the Name: The Billion-Dollar Business
You can’t talk about Jessica Simpson and her sister without talking about the "Jessica Simpson Collection." It’s a retail monster. But people forget that Jessica and her mother, Tina, had to fight tooth and nail to buy that brand back in 2021.
By 2026, the brand has been completely rebuilt as a digital-first, community-powered business. They isn't just selling shoes in Macy’s anymore. The 2024 Walmart collaboration—which brought 100+ SKUs under $30 to the masses—cemented Jessica’s status as the "aspirational everywoman." She knows her audience. She knows they want style that fits a size 3X and doesn't cost a month's rent.
What most people get wrong about their wealth
- It wasn't easy: They almost lost the rights to use the name "Jessica Simpson" entirely during the Sequential Brands Group bankruptcy.
- It's a family affair: Tina Simpson is the backbone of the operations. Ashlee has often been involved in the creative side of the younger-skewing lines.
- Net Worth vs. Value: While the brand has been valued at $1 billion, Jessica’s personal net worth in 2026 is estimated around $200 million. Still, not bad for someone once mocked for her "dumb blonde" persona.
Navigating Heartbreak Together
Let’s get real. The last year hasn’t been all glitter and Las Vegas lights. Jessica’s split from Eric Johnson after a decade of marriage was a massive blow. People started speculating she’d be the next Bachelorette, which she laughed off at LAX recently, saying she has "options" and doesn't need a reality show to find a date.
Through the "frosty" periods of the separation, Ashlee has been the anchor. When you're a Simpson, your family is your fortress. We saw this back in 2004 during Ashlee’s Saturday Night Live lip-syncing mishap. Jessica was the first one to jump to her defense, calling the criticism "obscene." That same energy is what’s carrying Jessica through her divorce now.
They’ve both faced the "not good enough" feeling that plagued their early careers. In recent interviews, Jessica reflected on how alcohol used to silence her intuition. Today, both sisters are focused on "unconditional love" and showing their kids—Maxwell (13), Ace (12), Birdie (6), and Ashlee’s trio with Pete Wentz and Evan Ross—that you can stay friends with your ex and stay close to your sister.
Actionable Takeaways from the Simpson Sisters
Watching the evolution of Jessica Simpson and Ashlee Simpson provides some surprisingly solid life lessons for the rest of us.
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- Reclaim your narrative: If you feel like your "brand" or career is being handled poorly by others, don't be afraid to pull a Jessica and buy yourself back.
- Support isn't a competition: Ashlee’s success in 2026 doesn't take away from Jessica’s; it adds to the family legacy. Celebrate your friends' wins like they're your own.
- Vulnerability is a tool: Jessica’s Nashville Canyon and her memoir Open Book worked because she stopped trying to be perfect. Authenticity sells better than a polished lie.
Whether they finally release that sister collab or just continue dominating their respective lanes, the Simpson sisters have proven they aren't just relics of the 2000s. They’re a blueprint for how to handle fame, family, and a billion-dollar business without losing your soul—or each other. Keep an eye on Ashlee's final Vegas dates this month; if history repeats itself, Jessica will be right there in the wings, cheering the loudest.