Ashlee Simpson Looks Back on Her ‘Pieces of Me’ Y2K Fashion

Ashlee Simpson has no regrets about the pieces of fashion she pulled off when launching her music career 20 years ago.

“Honestly, I mean, I kind of love it,” Simpson, 39, exclusively told Us Weekly when partnering with Dairy Queen to celebrate the first day of summer. “There’s certain things where I’m like, ‘Wow girl, what was that?’ There was a moment when I wore, like, wrestling boots and a skirt that was different, but I think I was all about taking those chances. So go Ashlee go. Go 19-year-old Ashlee.”

One look that may never go out of style is Simpson’s attire for her “Pieces of Me” music video.

When her debut single was released in 2004, The Ashlee Simpson Show star released an accompanying music video. In the final project, Simpson sported a pink polka-dot skirt and a white tank top with “Punk” written across the top.

Related: Ashlee Simpson and Evan Ross’ Sweetest Family Moments

Ashlee Simpson and Evan Ross wear a lot of hats as musicians, reality stars and actors — but they are doting parents too. The “Pieces of Me” singer welcomed her first child, son Bronx, with her ex-husband, Pete Wentz, in 2008. Following their 2011 split, Simpson moved on with Ross and welcomed their daughter, Jagger, […]

While some fans may remember the outfit details, Simpson won’t forget her hairstyle that turned out to be a last-minute decision.

“I had dyed my hair the night before,” she said. “I finished 7th Heaven. I wrapped for that day. I went home and bought box dye and dyed my hair dark and I was like, ‘Guys just so you know, I’m coming in tomorrow to shoot the video with dark hair.’”

“And then I really got that mullet going,” Simpson added with a laugh. “Don’t tell me I can’t have a mullet!”

Nearly two decades later, some of the looks have caught the eye of Simpson’s kids including 8-year-old daughter Jagger. (She also shares Bronx, 15, with ex Pete Wentz and Ziggy, 3, with husband Evan Ross.)

“I remember with Jagger, she went down all my music videos and put on her double belts too,” Simpson said with a laugh. “She’s like, ‘Mommy I want you to go on tour and I want to sing with you.’ It’s cute.”

As part of her partnership with Dairy Queen, Simpson isn’t just looking back on her biggest hits. She’s also celebrating some of the “Greatest DQ Hits.” This summer, the DQ Freezer will give fans the chance to enjoy re-releases of their favorite blizzard treat flavors including the Brownie Batter Blizzard Treat and Frosted Animal Cookie Blizzard Treat.

“This DQ freezer is so much fun because it holds so many old good flavors from 2004 and for me, it’s my 20-year anniversary of Autobiography and I remember being on tour and being like, ‘Stop at the Dairy Queen’ and I would literally have the Brownie Batter Blizzard so it fully brought me back,” Simpson said. “Even tasting it again, I thought, ‘so good.’”

Now that she’s a mom of three, Simpson also loves having the opportunity to take her kids to Dairy Queen for special treats.

“The blizzards were always my favorite. I definitely have this memory of growing up and it’s been so fun to even share it with my kids,” Simpson reflected. “It’s been such a fun partnership and looking back on 2004 and what we were wearing, the music and everything, I can’t believe it’s been 20 years.”