From Popdust

Katie Holmes Is in Her Chaotic Y2K Era

Katie Holmes is chaotic-good personified. I really believe that.

Why else would she step out to the 2022 iHeartRadio Jingle Ball in New York City wearing the most quintessential Y2K combo: a strapless mini-dress over frayed blue jeans?


You heard it right — the jeans-over-dress combo is back. In the year of our Lord 2022. And even though we swore we wouldn’t let low-rise denim return, it’s here. And now, inevitably, we must reap what we have sown. The harvest: the dregs of Y2K fashion.

It’s giving Disney Channel. It’s giving Teen Vogue Party. It’s giving Y2K at its peak. She would know! She was a style icon in the early 2000s, and she’s not letting us forget it.

Katie is no stranger to a viral outfit photo. She single-handedly made that Khaite cardigan set go viral simply by hailing a cab — the photo that launched a thousand knit bras. And lest we forget: she survived a marriage to Tom Cruise. She can do anything! But should she?

The Dawson’s Creek alum made a bold proclamation with this look. The Y2K renaissance is not just for baby Gen-Z’s who never lived through that war of kitsch and chaos. More chaotic, even, than Portia in White Lotus.

So if you’re tempted to recreate your own version of this nostalgic look, here’s how I'd do it. If you're not, enjoy this outfit post-mortem:

All products featured are independently selected by our editors. Things you buy through our links may earn us a commission.

Medium Wash Baggy Jeans

The era: 2000-2007. The jeans: baggy, frayed. To recreate this look, go vintage. Or vintage-inspired. A straight leg cut and a teeny distressed edge is the key to nailing this 2000s vibe.

A Mini Dress/Tube Top

This is the crux of the chaos. It has to be long enough to be almost a dress but short enough to be almost-a-top. Did you get that? Are you taking notes? And make sure it’s strapless and fitted to juxtapose against the long, loose fit of the jeans.

Some Black Sneakers. Literally Any. Your Running Shoes Work.

Make it hip and modern by choosing your favorite pair of black sneakers. Even a cheeky ballet flat would work here. The more chaotic, the better

More from Trueself