How Ashlee Simpson’s Daughter Feels About Her Mom’s Y2K Style

Jagger Ross may be a fan of some of her mom’s old-school looks, but she wouldn’t have gotten there without a push from modern Y2K stylings. As Ashlee Simpson explained to Elite Daily, “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.”

This description reminded us of Simpson’s 2004 Radio Music Awards ensemble, where she paired a teal tulle skirt with black and white wrestling boots. A white graphic tee layered under a frilly spaghetti-strap top, a yellow grommet belt, and some eclectic jewelry make up the rest of the outfit, creating a quintessential early 2000s look. While it has some distinct differences from Olivia Rodrigo’s SOUR tour looks, we can definitely see the connection.

“It’s just so of that time, of that era,” Simpson told Page Six about this specific look. “It’s fun to look back and laugh at it. I would not be caught dead in that 1699292052.” Even if her layered look doesn’t hold up today, at least its Y2K origins are something she and her daughter can still bond over.