Jessica Simpson Stuns in Country Comeback 16 Years After Infamous High-Waisted Jeans Incident
Fans still remember one of Jessica Simpson‘s toughest public moments from nearly two decades ago. Her high-waisted denim and leopard-print belt look spurred a media firestorm in 2009. Critics made horrific comments about her body that would not fly in 2025.
Now, 16 years later, Simpson is returning to her musical roots amidst a divorce from her longtime husband, Eric Johnson. On March 13, she surprised fans with a special performance at Willie Nelson’s Luck Ranch in Spicewood, Texas. Whether intentional or not, the 44-year-old channeled her infamous 2009 look in a unique way.
In 2009, Jessica Simpson performed at the Chili Cookoff in Pembroke Pines, Florida. She wore high-waisted jeans with a thick leopard-print belt. The outfit included a black tank top and “mom jeans,” sparking tabloid scrutiny and body shaming. In hindsight, the controversy highlighted unrealistic body standards and body-shaming culture in Hollywood.
In later years, Simpson stated that the backlash affected her deeply but helped her stand up for herself and embrace her body more confidently. “What’s so unbelievable is that I was probably at least 15 pounds smaller than I am right now,” she shared with Redbook in February 2014. (She was a size four at the time.) “What’s more unbelievable is that the press could create something like that out of a pair of jeans.” She called the criticism “ridiculous and unfair.”
Simpson channeled her 2009 look at Nelson’s ranch outside of Austin. Surprising fans with a performance at the Luck Reunion country music festival, the mother of three performed several songs, including “Leave” and “Use My Heart Against Me,” as well as her versions of “Son of a Preacher Man” and “These Boots Are Made for Walkin’.”
Simpson wore a snug leopard-print maxi dress and knee-high brown leather boots. She accessorized with a Native American-inspired concho belt studded with turquoise. The Dukes of Hazzard actor layered a cropped knit cardigan over the look, adding turquoise statement jewelry to her fingers and neck. In addition to Simpson’s leopard tribute, her backup singers wore the print, and a table onstage featured leopard, too.
Simpson posted several clips from the festival on Instagram, writing, “@luckreunion is a reminder that no matter what lies ahead of me, @willienelsonofficial is ALWAYS there! Thank you Uncle Jesse and Luck Reunion for reminding me that these boots were made for walkin’ (back on stage) I’m blown away and shook with gratitude as an independent artist and musician by all the love I received tonight, it was truly electrifying’. I love y’all!”
Simpson’s performance echoed the singer we know from the early aughts. With her leopard print look, she gave the middle finger to those trolls who body shamed her years ago. “This lucky voice gets to soar again tonight … More to come,” she posted on Instagram.
