of all things hot. Her latest endeavor, a collaboration with eyewear brand Quay, which raises money for the non-profit Project Glimmer, nods to a new girlboss era of advocating for young people forced into congregate-care facilities. We’d happily rally any aught icon’s comeback arc, but Hilton will seemingly never not be relevant. With an Instagram following upwards of 18.2 million, she embodies the influencer community at its best, vapid, albeit carefully manufactured, veneer be damned.

This begs the question: In a world where we’re constantly inundated with ads for new products, why launch sunglasses? “Well, as everyone knows, I’m obsessed with sunglasses,” Hilton said recently by phone. “I wear them all the time, even at night. Sometimes, when I’m walking out of a club and there are cameras or flashes, or if I’m taking a million selfies, it’s just better to have sunglasses on. When you wear sunglasses, you always look perfect.” (Fair enough.) The 12-piece collection features Y2K-inspired styles that pay sartorial homage to the trends of Hilton’s heyday. “I love anything that’s bedazzled and crystal-y and pink.” (Days after our conversation, WWD breaks the news that she’s releasing her own line of velour tracksuits.)

Yet even though Hilton has a celebrated past, she has her glittery eyes set firmly on the future. A recent video posted to Instagram of her and “Tom Cruise” using deepfake technology caused massive confusion online. “Everyone was calling me like, ‘Is that your Super Bowl commercial with Tom Cruise?’” Hilton said, laughing. But it’s just one of her many investments in the crypto space, a market she’s “obsessed” with. “You really need to dive in and be a part of the community because it’s here to stay,” she cautioned. “I was inventing the metaverse back in 2018 when I did my documentary The American Meme. I had my self-tanned avatar and created a Paris world where people could come and socialize. It’s just so new to everyone that if they don’t understand it, it’s hard for them to wrap their head around it. The technology is so fast; there’s something new to learn every second.”

She’s definitely been busy keeping up. Usually a Fashion Month fixture, Hilton was noticeably absent from shows this season because she was literally “in the metaverse,” she said, putting on a runway presentation, launching digital wearables, and even hosting an afterparty with online game platform Roblox. But in the spirit of nostalgia—and her new collab—we asked Hilton to indulge us in a game of This or That, inspired by ‘00s fashion trends. Her initial response? “Loves it.”

This or That

Baby tees or ribbed tank tops?

Baby tees.

Halter tops or tube tops?

Halter.

Double denim or velour tracksuits?

Obviously velour tracksuits, my uniform. I was never into the all jeans moment. I did it a couple of times for The Simple Life, but I didn⁠’t love it.

Low-rise jeans or wide-leg denim?

Low-rise jeans.

Sidekicks or Razrs?

Razr, because I was the one who launched the pink Razr. Actually, I launched the Sidekick as well [laughs]. Do they have Sidekicks anymore? I guess the Razr because they have them again now. Has to be bedazzled.

Moon Boots or Uggs?

Moon Boots. I love them⁠—they’re so cute with my snow bunny outfits when I go skiing in Aspen.

Tiny sunglasses or oversized sunglasses?

Extra-large.

Fendi Baguette or Louis Vuitton Pochette?

LV.

Crimped hair or zig-zag parts?

Crimped hair.

Bandanas or butterfly clips?

Butterfly clips. I just bought a bunch of them. They’re coming back.

Kitson or Fred Segal?

Kitson.

Mini skirts or matching sets?

Mini skirts.

Baby Phat or Ed Hardy?

Baby Phat, always.

Trucker hats or tiaras?

Tiaras.