Ashlee Simpson's Fashion-Forward Daughter Unaware of Her Iconic Early 2000s Style

Festival di Cannes 2023(Photo by Daniele Venturelli) Daniele Venturelli/WireImage

During the early 2000s, Ashlee Simpson achieved fashion icon status among angst-ridden teenagers. Her effortlessly cool choppy haircut, low-waisted cargo pants, and heavily layered shirts captivated us all.

Fast forward to the present, and Y2K fashion has made a comeback. At 39 years old, Simpson is rediscovering the nostalgia of those good old days through her 8-year-old daughter, Jagger, whom she has with her husband Evan Ross.

Simpson shared her nostalgia for her past outfits during an interview with Elite Daily, published on October 25. She reflected on her daughter's admiration for Olivia Rodrigo and their bonding moment over ballet outfits. Simpson humorously mentioned that she used to wear tutus with wrestling boots back in the day. Apart from their daughter Jagger, Simpson and Ross also have a son named Ziggy Blu, who is 2 years old. Additionally, Simpson has a 14-year-old son named Bronx Mowgli from her previous marriage to Pete Wentz.

In the same interview, Simpson fondly recalled her teenage years in the spotlight and reflected on her fashion choices. "During my youth, I used to insist on shopping in the Tommy Hilfiger boys section," she shared with Elite Daily. "I had a fondness for the baggy jeans, crop tops, and all those [Y2K] trends. Sure, there were some blunders, but that's what made it enjoyable."

Simpson acknowledged that her older sister, Jessica Simpson, has greatly influenced her current fashion and beauty preferences, openly confessing to borrowing the singer's clothing.

"We used to have such distinct tastes, but now my sister and I constantly work together on beauty concepts," Simpson revealed to Elite Daily. "One of my favorite activities is experimenting with makeup alongside her. I'm always curious about what she uses on her skin."

Simpson credits Jessica for introducing her to the skincare brand Biologique Recherche and Chanel eyeliner pens. On the other hand, Simpson has persuaded her sister to try the highlighter by Pat McGrath.

Regarding a beauty trend that Simpson longs for from the 2000s? Blue eyeshadow. "It's absolutely captivating," expressed the Piece of Me singer during the same interview. "I believe it's time for it to resurge."

Although we indeed long for Simpson's daring and innovative style from years ago, her present fashion selections have undoubtedly been anything but underwhelming.

Simpson exuded chic elegance at the 2023 Vanity Fair Oscar Party, donning a stunning yellow sequin Tony Ward gown. While embodying her punk rock heritage, she added a touch of edginess with a sleek coat of moody black lipstick.