Katie Holmes Y2K Fashion: Are Dresses Over Pants A Good

Photography by Getty Images

Y2K has finally gone too far.

By Natalie Michie

Date December 13, 2022

The year is 2005. Bedazzled Motorola Razrs are the definition of high-tech. Destiny’s Child is still together. Disney’s cinematic masterpiece, Ice Princess, has just hit the scene, and young Hollywood royalty is congregating to attend its premiere. Ashley Tisdale emerges onto the red carpet wearing a white graphic T-shirt that reads “Dream Bebe,” a pair of bootleg jeans, and a gold sequined mini-skirt layered over top. Just like that, history is made.

What Tisdale didn’t know then (or did she?) is that her outfit would go on to be immortalized in internet lore. In the years that followed, the outfit-turned-meme has become an emblem of regrettable 2000s fashion, serving as a cautionary tale about the tacky wardrobe blunders of decades past. But as today’s appetite for Y2K rages on, this once-maligned styling choice — messy as it may be — is making a very real comeback. Case in point: Katie Holmes.

On December 9, at the iHeartRadio Jingle Ball in New York, the actor went viral after donning a fitted mini-dress atop a pair of frayed, slouchy straight-cut jeans. Her footwear of choice? Not heels, not flats, but a pair of New Balance sneakers. (Chaotic.) While we can — and will — endlessly debate her specific styling decisions, the overall outfit points to a more severe sartorial statement: somehow, this layered look is once again red carpet wear.

Though Holmes’s ensemble was actually a very long tube top (plot twist!), the mini-dress-over-pants-reminiscent ensemble immediately brought the world back to the land of outlawed fashion. Many even mistakenly thought the image was from the early 2000s instead of last Friday. Alas, we’re sadly not living in a Disney channel fever dream — quite the contrary. With this look, Katie Holmes is showing the world what real Y2K fashion looks like. And it ain’t pretty!

In the early aughts, this polarizing style was ubiquitous. Sported by icons like Britney Spears, Anne Hathaway, Lil Kim and Miley Cyrus, the red carpet approach back then was clear: don’t think, just layer. Sure, low-rise jeans, baby tees and mini skirts were all part of it, but this questionable aesthetic is what ruled the fashion of the bygone era. And soon, it may very well rule this one.

In recent months, trendsetters like Dua Lipa and Bella Hadid have recklessly paired skirts and dresses with pants. The style has taken off on TikTok, too, where fall and winter #OOTDs are filled with variations of the maximalist style. Not to mention, the trend was a staple of the fall 2022 runways. Brands like Chloé, Peter Do, Off-White, Jacquemus and Proenza Schouler presented their take on dresses over pants, from modernized monochrome ensembles to avant-garde cutouts. Point is, love it or hate it, it’s here to stay.

In the absurdist fashion landscape of 2022, it isn’t all that surprising to see this divisive trend return. Maximalist layering has been having a moment since the dawn of the new decade, as outfit trends call for mixed textures, asymmetrical styles and clashing patterns. With the growing appreciation for over-the-top Harajuku clothing and the glorification of the “weird girl” aesthetic, today’s fashion is intentionally all over the place. As such, dresses over pants are a natural extension of this more-is-more ethos.

It’s not all bad. For one, the layering possibilities are endless, encouraging wearers to play around and break fashion rules. Plus, it’s a way of adding coverage to skin-baring designs like micro-minis or teeny going-out dresses. Because it’s so counter-intuitive, going overboard in this style is really the only way to make it work. And we suppose there’s something poetic about wearing an ensemble that makes absolutely no sense. Metaphors aside, seeing the look on Katie Holmes activates a wave of nostalgia — and not the good kind.

Ultimately, her recent viral outing has left us with more questions than answers. Is she unironically making the case for the return of dresses over pants? Or is she warning the world about the kind of red-carpet crimes that might ensue if we continue to glorify the garish get-ups of the early 2000s? We may never know. Nevertheless, we’re sure Ashley Tisdale is proud.

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