Pop culture’s current obsession with all things Y2K is nothing new — but it also shows no signs of slowing down. And as more fans look back on Jessica Simpson‘s twenty-plus years in the spotlight, from pop princess and reality TV pioneer to footwear mogul and 2023 FNAA Icon Award winner, they are also discovering just how influential the star’s Y2K fashion moments were, then and now.
“I honestly keep everything — too many things,” said Simpson, on the set of her FN cover shoot to celebrate the award. “I feel like Y2K will always come back.”
The star admits that she has not one but two storage units that contain her looks from over the years. Not only has she kept most everything from her career — she also remembers all of the details of where and when she wore the looks.
“I just went back and grabbed stuff. And of course I have to tell everybody everything. ‘And this is what I wore when I went to the bathroom in New York, this one time when this paparazzi tripped,'” the star joked. “I remember the stupidest details of everything. But they all have a story. Maybe I should write it down and do a fashion book or something. You never know.”
Here, Simpson breaks down eight of her most memorable looks from the height of her pop career, which also happened to coincide with the Y2K era’s peak fashion years.
2003 – Michael Kors Runway Show at New York Fashion Week
“I loved it so much because I didn’t have to wear a bra and it was very fashion for me at 23 years old,” said Simpson. “That’s when I actually met Michael Kors and he was so kind and generous to me. He let me take the dress home. It was in my closet until I got pregnant with Maxwell, and I never thought I would lose the weight to wear it again. I actually want it back! I wish I hadn’t given it away!”
2004 – The Reality Tour
“This dress was made by Roberto Cavalli, a very dear friend of mine. He really knew how to dress my body especially for stage. By the end of the tour I was spilling out of this dress and it broke in multiple places, but it hung in all summer somehow. I do still have it, it’s in storage.”
2004 – MTV Video Music Awards “
“This is styled by Rachel Zoe, it’s a Valentino dress. I love the metallic, anything bold but also sophisticated. I loved wearing the short hair with it, I felt like I was giving off a different vibe than most people do at the VMAs.”
2005 – “Dukes of Hazzard” Premiere
“My very first role, Daisy Duke. My stylist at the time was Jessica Paster and she took me into Narciso Rodriguez and we picked out this periwinkle blue color. I just loved it so much. I felt like a movie star!”
2005 – Out in New York City
“I was in my element. I am a jeans girl so if I can dress up jeans in any way, it’s going to be with a corset and a BIG flower. I do still have it. This is a good one to keep.”
2005 – ESPY Awards
This is probably one of my all-time favorite dresses. It is just the most classic dress. I had never worn anything fit and flare before. I love the yellow and the cream, it’s Oscar de la Renta. I remember I could hardly breathe. My favorite part is the accessory – the corsage.”
2005 – MTV Video Music Awards
“This was a big year for me. It’s not really a VMAs look. A lot of people don’t wear shorts. But I was Daisy Duke, so I wore shorts. And it was very scandalous because you could see my lace bra. And now it’s so normal. This is a Y2K top. I don’t know if I still have it. Would I wear it again today? Probably, but not with shorts.”
2006 – Performance for “A Public Affair”
“This was press for my last pop record that I did. I had short hair, I just chopped it all off. I was going through a divorce and I just said take it all off. I just wanted to wear something that was comfortable. I love the color. And then I wore a Jessica Simpson Collection boot. 2006 was a big boot moment, that’s when we started launching a lot of things with the brand. I do still have these boots. I just thought it was fun that you could fold them over. Maybe that will come back one day, but it’s a little Renaissance or something.”
