Ashlee Simpson Teases New Music & Reveals How She’s Bringing Back Her Y2K Era

So much has happened since the 2000s, from fashion to technology; but that doesn’t mean we don’t miss the Y2K. It was a simpler time full of chunky accessories and fun music we still have on our playlists in 2024. It’s no wonder why we’re emulating the times with our fashion again, and thanks to Ashlee Simpson (and Dairy Queen), we’re one step closer to reliving the good ol’ days of Y2K.

Not only is it the 20-year anniversary of Simpson’s iconic album Autobiography, but Dairy Queen, also known as DQ, is ready to give everyone some nostalgia. Think about it, chances are, you jammed to Autobiography while eating your favorite Blizzard. While so many of our favorite Blizzards are of the past, DQ is bringing it back with the DQ Freezer, which holds all the iconic Blizzard Treats ever created! Opening for the first time this past spring, you can munch on your favorite Blizzard treats over the years.

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To celebrate these two events, Simpson is dishing on everything from the partnership, Y2K fashion she adores, and even if new music is on the horizon.

Dairy Queen.
Dairy Queen.

When you sit down to chat with Simpson, you can feel the excitement through the screen. She has a zest for life that’s almost infectious, and when she discusses what she loves, including the partnership. “DQ partnership has been so much fun and so nostalgic so I really enjoy doing it,” she said, talking about how her favorite has to be the Brownie Batter Blizzard Treat.

“Doing this, we just totally referenced 2004,” she said, adding, “It’s the 20-year anniversary of Autobiography. I feel like on tour, we used to stop at Dairy Queen. I was like, this is awesome.”

Speaking of her tour, when asked what she was most proud of in her career, it was definitely her tour, the Autobiography Tour in 2004; along with her other two tours, the L.O.V.E. Tour and Club Tour.

“I would definitely say for me, in my career, being on tour was my favorite. Even now, when I see people who were on my tour, they’re like, ‘That was the best moment.’ I feel like it was just such an amazing time connecting with my fans,” she said, also noting how every fan interaction is her “favorite.”

Ashlee Simpson
Ashlee Simpson

Autobiography was such an iconic moment in our lives, and even today, we’re grooving to the songs and singing our hearts out to the lyrics. But what is Simpson’s favorite song? “La La.” It’s “always fun. When I performed that with Demi Lovato, it was fun to go back and do that and have that moment again.”

When I asked her about what advice she’d give her younger self during her first tour, she immediately said she’d tell her younger self to “enjoy every moment.”

She said, “I would say, just enjoy every second and not take everything so seriously that, you know? Things may seem bigger than they are. That is what I would give my younger self.” Perfectly said!

But the question on everyone’s mind is: Will Simpson release new music? Get ready fans, because yes, she definitely is!

“Yeah, it is on the horizon. Right now we’re gonna have a vinyl come out, and then I will have new songs coming out soon. It won’t be this summer, but it’ll be very soon,” she said, so keep your eyes peeled!

Dairy Queen.
Dairy Queen.

Now, ever since the 2000s, Simpson has been both a music icon, and a fashion icon. She’s done so many trends over the years, from her punk-rock phase to the boho-chic vibes. When asked about her style in 2024, she said, “I have a mix. I’ve always loved vintage, even back then. [Today] it’s a bit more elevated.”

And since her fashion is a mix today, that means she’s not opposed to rocking some good ol’ Y2K trends.

“[When] shooting this with Dairy Queen, I kind of dressed in that 2004 vibe. It was so funny. I was like ‘Wow, we wore a lot of accessories.’ I had too many belts on! [But] I loved the cargo shorts that I always wore, and for me, that still remains solid. And the green Converse. I always had green Converse on and my cargo pants!” She also noted her love for spiky belts, and Alexis Butar Bracelets; but also noted she’d be happy if the “super super low jeans” didn’t see the light of day again. (We totally get that!)

Music, fashion, and all that nostalgia! What more could we ask for? If you need some words of wisdom, Simpson did say to us, “It’s the 20-year anniversary of Autobiography! Everyone needs to go get a Blizzard, stream Autobiography, and wear lots of spiky belts.”

If you have any questions about The DQ Freezer, check out the FAQ board and go to the DQ Mobile App!

Before you go, click here to see the most dramatic celebrity hair transformations.

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