In the early 2000s, Ashlee Simpson was heralded by fellow angsty teenagers as a fashion icon. Her choppy too-cool-for-school haircut, baggy low waisted cargo pants and excessively layered shirts had us all in a chokehold.
Now that Y2K fashion has come back in style, Simpson, 39, is reliving the good old days through her daughter, Jagger, 8, whom she shares with husband Evan Ross.
“It’s kind of great looking back at my outfits from back in the day,” Simpson told Elite Daily in an interview that was published on Wednesday, October 25. “My daughter loves Olivia Rodrigo, and when she’s like ‘I like her ballet outfit,’ I’m like, ‘Jagger, mom used to wear tutus all the time … but with wrestling boots. So there was a moment between us right there.”
In addition to Jagger, Simpson and Ross also share son Ziggy Blu, 2. Simpson shares son Bronx Mowgli, 14, with ex-husband Pete Wentz.
In the same interview, Simpson reminisced on her fashion choices as a teenager in the spotlight. “When I was younger, I would tell my mom I only wanted to shop in the Tommy Hilfiger boys area,” she told Elite Daily. “I love the baggy jeans, the crop tops, all that [Y2K] stuff. Yeah, there are some mistakes, but that’s what’s fun about it.”
Simpson made sure to credit her famous older sister Jessica Simpson in influencing her current fashion and beauty choices, admitting to borrowing the singer’s clothes.
“I feel like we used to be so different, but my sister and I collaborate so, so much on beauty ideas now,” Simpson told Elite Daily. “My favorite thing is for us to play makeup together. I’m always like, ‘What are you using for your skin?’”
According to Simpson, Jessica has influenced her to use the skincare brand Biologique Recherche as well as Chanel eyeliner pens, while Simpson has gotten her sister to try out a highlighter by Pat McGrath.
As for a beauty look from the 2000s that Simpson misses? Blue eyeshadow. “It’s a total vibe,” the Piece of Me singer said in the same interview. “I think it’s time for that one to make a comeback.”
While we do admit to missing Simpson’s edgy experimental style from decades ago, her current fashion choices have proven to be far from disappointing.
At the 2023 Vanity Fair Oscar Party, Simpson looked chic and elegant in a yellow sequin Tony Ward gown. Of course, she hasn’t completely forgotten her punk rock roots, as she finished the look off with a swipe of moody black lipstick.
