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I Tried Wearing Dresses Over Pants
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I Tried Wearing Dresses Over Pants

Wearing dresses over pants may be fashion’s latest fixation but how does the trend fare 20 years past its prime? Writer Jennifer Nguyen finds out.

By Jennifer Nguyen

Every time I’ve worn a dress over a pair of pants it has been against my will. In elementary school, my mother paired my La Senza Girl dress with leggings to account for my constant clumsiness. At the airport, I once overpacked my luggage and was forced to frantically toss on a sweater dress and silk blouse over my sweats to convince the gate agent to let my carry-on go in the overhead bins. And then there’s weather-induced layering, an unfortunate byproduct of living in Toronto where winters drop to -20ºC. But to willingly put a dress over a pair of pants in 2024? I’d never! Well…that is, until now.

While many will remember the trend most fondly in the 2000s (see Anne Hathaway in a pink dress over jeans at the Ella Enchanted movie premiere and Miley Cyrus in a blue silk dress worn over jeans at the 2006 Teen Choice Awards), the styling choice has recently had a massive resurgence, especially on social media. The hashtag #dressesoverjeans — championed by digital creators like @readwritethrift and @hodanyousuf— currently has 18.7M posts. On the runways this past Spring season, the trend was everywhere, from Issey Miyake layering some bottoms with two (yes, two!) dresses to Khaite sending a sheer white dress with simple black pants down the catwalk. Are all these fashionable folks onto something? Could these fashion moments translate to day-to-day dressing? Could I be a current-day dresses-over-pants convert? Spoiler alert: the answer is yes, and I think I nailed it. Here’s what I came up with.

Day One: Venus Maxi Dress by Blush, Linen Pants by Reformation

I Tried Wearing Dresses Over Pants
Photography courtesy of Vanessa Cassar

To begin this highly scientific experiment, I started with a sheer dress from Blush. Yes, I chose to “ease” in with a dress that’s technically lingerie. In my defence, the transparency felt less like a full-on dress and more like an accessory. I paired it with linen pants from Reformation and anchored the look with some classics (Attire navy blazer, Loewe bag, and flats from Maguire) to balance out the nostalgic styling method. And while I did earn an odd glance from my concierge as I was on my way out to dinner with some friends, said friends reassured me, taking away some of my self-consciousness.

Day Two: Nicia Dress by Sézane, Anti-fit denim by Kotn

I Tried Wearing Dresses Over Pants
Photography courtesy of Vanessa Cassar

The next day, I decided to tone things down with a simple A-line number from Sézane worn over a pair of blue jeans from Kotn. As a Y2K-era ode to The Devil Wears Prada (it’s incredible how many of the costumes still feel modern today), I took a cue from Andy in The Devil Wears Prada and topped off the look with a brown leather jacket from ba&sh, biker boots from Aldo and a cow print bag. In this ensemble, I was able to breeze through my day without a single double-take. Coffee run? Check. A pit stop in the park? You betcha. Heck, it even warranted a compliment from my pal Vanessa who took this pic. Success!

Day Three: Draped Midi Dress by Smythe, Agency Pant by Aritzia

I Tried Wearing Dresses Over Pants
Photography courtesy of Vanessa Cassar

Ripping off the final bandaid, I broke out a fancy wrap dress from Smythe (a cocktail dress on a typical Tuesday? Who would’ve thought?) and paired it with wool pants from Aritzia, a Burberry trench and Bottega Veneta bag (both from local consignment store Mine and Yours), and funky frames from Bonlook. As the most obvious ode to the trend, this ensemble warranted the most stares, and, to my surprise, the most compliments from strangers on the street. However, practicality was a bit of an issue. The tight dress paired with the pants was pretty restrictive and made errand running and coffee meetings harder than usual. At least I looked great while doing them.

Conclusion: Embrace your inner Miley and Anne

What began as an involuntary fashion experiment quickly became a viable styling method that I’d willingly, even enthusiastically embrace! But learn from my missteps: Stick to shorter, sheer-er, or asymmetrical dresses with loose silhouettes. They pair best with pants and allow maximum movement. Also, don’t fear the stares. The trend is divisive and will attract both positive and negative attention, but, as long as you’re comfortable and like your outfit, it doesn’t really matter what others think. So next time you’re wondering what to wear in your wardrobe and find yourself contemplating between a dress or pants, choose the secret third option and say “Why not both.”

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Photography by Vanessa Cassar. Graphic by Lindsay Patterson
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