Jessica Simpson Strips Down to Her Lingerie for a Sultry “Afternoon Playin’ Dress Up”
Jessica Simpson Strips Down to Her Lingerie for a Sultry “Afternoon Playin’ Dress Up”
Rachel BurchfieldSun, October 25, 2026 at 2:51 PM UTC
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Jessica Simpson on September 7, 2025.Credit: GettyThe Gist -
Jessica Simpson modeled some looks from her namesake Jessica Simpson Collection, the multi-million dollar brand she founded in 2005.
On October 24, the singer posted a carousel of photos to Instagram of pieces from the line, including a black-and-white shot of herself in a bra and panties with a denim jacket atop the lingerie.
“An afternoon playin’ dress up in the Hollywood Hills,” she wrote alongside the images.
Jessica Simpson is showing off new pieces from her Jessica Simpson Collection—including a black-and-white shot of the singer stripped down to her bra and panties with a denim jacket atop the lingerie.
In the photo—posted as part of a carousel on October 24—Simpson completed her sultry look with hoop earrings, her blonde hair worn down and wavy. Other photos in the carousel include the mom of three standing barefoot in the front seat of a convertible wearing a short-sleeved animal print dress and gold jewelry; a black-and-white shot of Simpson atop a piano; an image of her in a scoop-neck gray top, dark wide-legged pants, and platform heels; and a photo of Simpson leaning up against a car in sunglasses, an animal print bustier, fur coat, black leather pants, and heeled sandals.
Jessica Simpson in New York City on July 23, 2025.Credit: Getty
“An afternoon playin’ dress up in the Hollywood Hills captured on film by Jason Lee Parry,” Simpson captioned the collection of photos. “I hope y’all are lovin’ these timeless pieces, exclusively at Walmart.”
Simpson launched her multi-million dollar eponymous brand in 2005, and in addition to clothing, the line sells shoes, accessories, perfume, and luggage. As the brand turned 20 years old in 2025, she told People, “Now, I have another 20 years to build something just as successful or keep this going for another 20 years, which is a very beautiful thing to celebrate.”
“Dreams really can come true,” she told the outlet.
Jessica Simpson on July 23, 2025.Credit: Getty
These days, “I definitely dress for myself,” Simpson added. “Whereas my younger self used to dress for guys, or for other girls to compliment me, or for attention.” She noted, “I think I’m more confident now in just a white tank top and shorts or leather pants.”
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“Our purpose is to keep going and to keep expanding and to stay as real and relatable as possible with the best prices,” she continued. “It’s a beautiful thing that we’ve made it this far and it’s still growing. I definitely wouldn’t be where I’m at without it.”
Of life now versus being in her mid-twenties when the line started, the 46-year-old said, “I wear life with more confidence. I feel better now than I ever did in my twenties. I think going through life and having all the opinions thrown at you—I’m at the place where only my opinion matters. And, of course, my kids. I don’t want to embarrass my children!”
Jessica Simpson on December 7, 2025.Credit: Getty
Simpson is mom to daughters Maxwell Drew and Birdie Mae and son Ace Knute, who she shares with ex Eric Johnson. After Simpson and Johnson confirmed their split in January 2025, in April of this year Simpson was romantically linked with boyfriend Thomas Eisenhood, a musician. Earlier this month, the two were seen in New Mexico together at Albuquerque’s Balloon Fiesta Park on October 4, per photos obtained by TMZ. Earlier this year, a source told People that Simpson was “happy,” adding, “She’s in a great place, excited for her future.”
Jessica Simpson at the 2025 MTV Video Music Awards.Credit: Getty
Saturday’s lingerie snap joins a bevy of bikini-clad photos Simpson has posted to Instagram lately, from a leopard print bikini in Turks and Caicos to a polka dot bikini marking her 46th birthday in July. Simpson has also been touring this year, and a source told Us in June of the singer’s new boyfriend, “Tom was on tour with Jessica on and off for the past few months.”
Jessica Simpson shares a photo of herself in a tiny polka-dot bikini while celebrating her 46th birthday on July 29, 2026.Credit: Jessica Simpson/Instagram
“Tom has been in the music industry for a long time,” the insider said of the former Stoop Kids band member, a group that was together from 2012 to 2023. “He tours a lot, so they spent a lot of time together by working closely. He is a very low-key guy, and Jessica likes that about him.”
on InStyle
Source: “AOL Entertainment”
