Can I Wear Sneakers With a Dress?

Given that Serena Williams wore sneakers with her Versace gown at the Met Gala a few years ago, and since then we’ve had two years of social isolation and comfort dressing, it’s fair to say that at this point sneakers with everything, everywhere is a thing — for pretty much everybody.

Let’s be honest: It’s hard to return to high heels, or even gladiator sandals. It’s hard to remember why we used to accept the idea of pain as an everyday part of footwear.

We have reached the natural end point of the trend born in the 1980s, when a legion of women put their heels in their tote bags and started commuting to work in aerobics shoes. See, for example, Melanie Griffith in “Working Girl.” Today sneakers are as much a part of a basic wardrobe as jeans and a white T-shirt.

Which is why every designer from Balenciaga (after recently causing a social media kerfuffle with sneakers made to look as though they had just emerged from landfill) to Chloé and on through the alphabet has sneakers as part of their offerings, no matter how haute.

Why Rei Kawakubo of Comme des Garçons has long featured her collaboration with Nike on her runways, paired with any number of fantastical concoctions that push the boundaries of what “clothes” even means. Why Maria Grazia Chiuri, Dior’s artistic director of women’s wear, paired pretty much every look in her 2022 cruise collection with sneakers. Why Vogue just announced that “sneakers and dresses are summer’s freshest pairing.”

Which in turn is why there is a sneaker for pretty much any outfit — or any dress. Indeed, they add a dash of cool or casual to an otherwise proper outfit, making it impossible to stereotype and giving it a go-anywhere vibe. You can be fancy and buttoned up on the top and ready to motor on the bottom.

Since prices range from the collectible, sneakers-as-art-form end to the accessible, you can pick and choose what fits both your budget and personality. It’s simply a question of getting the proportions right.

Above-the-knee frocks pair well with chunkier, heavier kicks and high-tops (any number of Air Jordans; take your pick), while mid-calf or longer looks are better with a slimmer, lower sneaker profile. Florals or ruffly, girlish dresses benefit from being matched with tougher sneaks, while flowy looks work well with vintage styles like Stan Smiths or Vans.

In fact, it’s possible that sneakers are actually the equivalent of today’s dressy flats. Just don’t forget the socks.

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.

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