Dress Over Pants: Is There A Stylish Way Of Wearing It Sans The Y2K Nostalgia?

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From butterfly tops to low-rise jeans, every controversial trend from the early 2000s has been revived in the last couple of years. But the most polarising of them all is the dress-over-pants trend. Most of your favourite Disney stars have worn this absurd combination on the red carpet in the early years of their career. This was a pre-stylist era but unfortunately a post-Getty period—hence, everyone from Hilary Duff to Ashley Tisdale has been captured wearing a blingy, frilly dress over an oddly fitting pair of denim in HD.


While the idea of wearing pants with a dress isn’t entirely whimsical on its—the lack of proportion and extensive layering made a very poor case for it back then. Over the years, fashion evolved and so did the mood boards. Stylists a.k.a celebrity sartorial saviours arrived on the horizon and taught them the art of balance. Even designers experimented with this trend in their own unique way—for the fall of 2022, Jil Sanders sent down a deconstructed white pleated dress look, punctuated with a pair of black trousers and Louis Vuitton paired a layered black slip dress with blue denim.


Nature was restoring its balance and celebrities were finally getting a hang of working a dress with pants—yes, we’re looking at you, Emma Watson. The Harry Potter alumni have sported the androgynous look on multiple occasions. From her Golden Globes, 2014 Dior ensemble to the most recent Harris Reed upcycled number—Emma’s dress-over-pants trick always lands, increasing the credibility of this trend. This was until Katie Holmes decided to disrupt it all.


Recently, the First Daughter actor broke the internet when she attended the iHeartRadio Z100’s Jingle Ball 2022 in a satin mini dress, Reformation jeans and Margiela sneakers. No smart silhouette, no intelligent cut, just a bad-old throwback to the fashion ghost of the 2000s. In Katie’s defence, in an interview with The New York Times, her stylist Brie Welch explained the ‘why’ behind this viral look. “We decided the rich colour and subtle bustier effect detailing of the top was elegant and would be fun if paired with jeans, creating a more youthful feel for Jingle Ball and the atmosphere there.” She shared.


Although, Katie may have not wanted to, will this open the floodgates to more y2k-inspired dress-over-pant looks? Not every attempt at looking young should come out of a trip to the past. Keeping up with Katie’s sentiments, but modernising it making it 2022-friendly—if you ever want to go down the dress-over-pants route, here’s how you can do it.

1. Rihanna


Trust Rihanna to nail two trends in a single outfit. Dress-over-denims but wear it the Canadian tuxedo way. The Umbrella singer wore her denim dress with a pair of jeans, matching boots and a baseball cap.

2. Zendaya


Zendaya kept it chic and formal in this Rahul Mishra look. The Euphoria star attended a Bulgari party in this sheer, 3D foliage-detailed dress, teamed with sharp black trousers. Talk about keeping it soft and solid all in one.

3. Phoebe Dynevor


The Bridgerton belle kept the y2k sentiment of this trend but gave it a rather contemporary treatment. Phoebe layered her shimmery LV slip dress on deep blue denim, a bralette and a black wrap skirt. On paper, all these elements may not work together, but Daphne Bridgerton made it not just work, but shine.

4. Serena Williams


G.OA.T Serena Williams turned model for Off-White when and flaunted this trend in a form-flattering manner. Sheer dress layered on a printed top with ruched matching fitted pants, another winning way of wearing dress-over-pants without alarming the fashion police.

For more trend-based stories, read here.

- Junior Digital Editor


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