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Walk into Urban Outfitters, Zara, or the nearest store today and you’ll be greeted by rows of cargo or “parachute” pants la Ciara circa 2006. Browse Pinterest, Instagram, or TikTok and you’ll see Gen Z favorites like Dua Lipa, Olivia Rodrigo and influencer Matilda Djerf flaunted a flamboyant sequin butterfly top like they’d just waved goodbye to 1999. But it was on the iHeartRadio Jingle Bell red carpet in New York last Sunday, when Katie Holmes appeared in true Y2K style in a blue Tove mini dress styled in raw jeans and black New Balance sneakers, the look went viral for all the wrong reasons.

Holmes wore her dress and jeans combo with black New Balance trainers. Credit: He was Suppressed/Getty
Primarily worn by the likes of Rachel Bilson, Ashley Tisdale, Zoe Saldana, and even Jessica Alba, the dress paired with jeans was an early 2000s red carpet staple. From pleated mini dresses to bohemian, halter-neck smocks, trends welcome all styles, colors and fits. But in later years, the combination was widely dismissed as a fashion faux pas, a foot in, one foot out energy often misconstrued as non-committal, or evidence of a casual type of clothing that seemed overly curated. But her formula, classic femininity balanced by something simple and androgynous, is the basis of many of the trends that dominate our social feeds today (think oversized blazers lifted over a vintage satin nightgown, or low-waisted trousers paired with a cinched bodice top). .
Holmes was met with excited headlines asking “was it 2002”, while descriptions of the aughts-inspired look ranged from “wild” to “too much”. The internet was, as always, more direct, with one Twitter user calling the ensemble “damned” and another joking that she should face jail time for her fashion style. The outfit even sparked an official response from Holmes’ stylist, Brie Welch, in a bid to manage the PR fallout. “We decided the rich colors and subtle bustier-effect detail on the top was elegant and would be fun to pair with jeans, creating a more youthful feel to the Jingle Ball and the vibe there,” Welch told the New York Times, adding with support that Holmes is “more than capable of looking cool in an accidental fad 20 years later.”

Jessica Alba wore the defining pair at the 2004 Teen Choice Awards in August. Credit: Vince Bucci/Getty Images
The real question isn’t whether Holmes’ clothes look good, but who are the gatekeepers to this fashion era? How do we collectively decide which relics of fashion history to revive, and which to leave to die and be buried? Because if a period of dressing needs a pinch of salt and an open mind, it’s a Y2K renaissance. Dubious comebacks include fluffy bucket hats, favored by Megan Fox; pedal pushers, as seen on Emily Ratajkowski; tie worn as a necklace (and without a collared shirt, according to Miley Cyrus); and little slogan tees, as seen on Addison Rae, just to name a few though neither faced any backlash from Holmes.

Jeans and dresses were the theme for Molly Goddard’s London Fashion Week Spring-Summer 2022 presentation. Credit: Ben Broomfield/Ben Broomfield @photobenphoto
But the union of dress and jeans, as unholy as some may feel, is here to stay. On the runways last season for Spring-Summer 2022, British designer Molly Goddard styled her fabulous tulle creation in a pair of baggy mid-wash jeans. For his debut at New York Fashion Week last September, menswear designer Peter Do layered a mid-length pleated skirt over trousers, and London-based label Chopova Lowena styled his favorite skirt over patterned trousers for Spring-Summer 2023. Although it probably stings for Holmes now, as the old saying goes: “You’re only mad until you make it, then you’re a genius.”
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