Katie Holmes’s Y2K Jeans Are Straight Out of ‘Dawson’s Creek’

If there’s one thing Katie Holmes knows, it’s how to seamlessly blend high fashion with the highly affordable. Sure, you might regularly spot the actor strolling through New York in off-the-runway Chloé dresses or Saint Laurent bags, but you’re just as likely to see her pairing them with Reformation sandals or Mango jeans. And as for the pricetag of that infamous Khaite cashmere bra and cardigan set? It was, undeniably, eye-watering—but Holmes did wear it with under-$200 sunglasses and a long-beloved pair of Acne Studios mules. She might like to splash out, but Holmes also knows a bargain when she sees one.

Yet even the most fully paid-up fans of Holmes’s laid-back, haute bohemian style must have had something of a surprise last night. Arriving at Madison Square Garden for the 2022 iHeartRadio Jingle Ball Awards, Holmes’s look didn’t just cherry-pick from across price points this time, but also from across the decades. In a strapless, deep blue mini dress worn over denim jeans—the frayed hems poking over the tops of her black New Balance sneakers—Holmes’s Y2K-inspired look embraced one of the most divisive trends of the season: skirts over pants. 

Back in September, Vogue’s Christian Allaire noted the increasing presence of this deceptively practical style solution both on the runway and in street style galleries, touching on both its early-2000s progenitors like Ashley Tisdale and the brands reviving it, including cult London labels Chopova Lowena and Stefan Cooke. Still, while I don’t disagree that it’s a thing, I have to admit, it wasn’t a trend I was expecting Holmes to get on board with. 

If anything, Holmes’s take on the dress-over-denim look reminded me of her first flush of fame as Joey on Dawson’s Creek. Joey’s love of dungarees, tank tops, and fisherman-style sweaters are all well-documented (and in the age of TikTok, probably overdue a revival) so to see Holmes lean into her Y2K style origins feels strangely charming. As long as a fully-fledged revival of frayed denim doesn’t happen? I’m down for Katie bringing it all the way back—and may the skirt-over-pant trend continue.