Jessica Simpson Revives Y2K Style While Celebrating Nashville Canyon Vinyl Success

Jessica Simpson went back in time to the early 2000s as she revived a babydoll crop top while celebrating a major milestone in her music career. The 45-year-old singer donned a cream midriff-baring cropped peasant top, an iconic piece straight out of the early 2000s, while promoting her Nashville Canyon vinyl on Sunday, December 14th, 2025.

She celebrated the huge achievement of fans snapping up a limited-edition Walmart vinyl of her new album, which almost sold out, with a medley video shared to Instagram. The I Wanna Love You Forever hitmaker’s blouse featured a high waist, a wide ruffled neckline, and long, elegant sheer sleeves, with a bow giving the nostalgic garment a cute finishing touch.

Also in the video, a cowboy hat could be seen placed on a table near the Dukes of Hazzard actress, adding a western vibe that tied into the album’s Nashville influence. Jessica, who recently swapped her signature blonde locks for a chocolate blonde shade, styled the look with a leather disc belt featuring silver hardware wrapped around her slim waist.

Jessica’s post comes days after the star admitted she did not feel “good enough” as a pop star during the early 2000s. Her rise to fame began with 1999’s Sweet Kisses, followed by Irresistible in 2001 and In This Skin in 2003.

© Steve Granitz

Speaking at a concert in Connecticut earlier this month, Jessica reflected on the pressures she faced at the height of her fame. She said that her whole music career felt like having a job, explaining that she was expected to be a pop star and tried her best, but when you are younger, you never feel good enough. 

She added that it is okay to not feel good enough sometimes and encouraged everyone to have grace for themselves during those moments. She went on to say that during particularly hard times in her life, she had to surrender to her intuition and focus on the light in front of her, reminding herself that her purpose was bigger than the moment she was in.

The Take My Breath Away performer also said that music felt more like a job than a calling in the early phase of her career. She explained that it was never really about the music, her voice, or her purpose, but about chasing hits and radio spins and making sure record labels recouped their investment.

© Kevin Mazur

Jessica admitted she felt creatively restricted, saying that while she was allowed to sing R&B songs, she was not allowed to write them herself. She said it did not feel authentic to who she was, but she had a job to do, and even though it was highly competitive, it taught her a lot. She added that the focus eventually shifted to dance moves and manufactured elements, saying that nothing ever felt good enough and that she is not a manufactured person.