5 Dresses You Can (and Should) Wear with Sneakers

The ultimate winter staple, a sweaterdress always looks put together but feels like pajamas—especially if you wear it with a pair of leather sneakers. Keep in mind that neutral colors will elevate the vibe even further, while a turtleneck silhouette adds another layer of elegance. Also note that, since you’re wearing flat shoes, you can get away with a shorter hemline as well as a midi length.

Get the look: Madewell dress ($118; $55); Topshop dress ($75); Adidas sneakers ($80); Treasure & Bond dress ($89); Veja sneakers ($120); Vince sneakers ($225)

Another great throw-on-and-go option, a shirtdress is ideal for those who might feel a little too girlie in some of the other styles listed here. (Not that there’s anything wrong with that—it all comes down to personal preference!) Mixing low-key chic with a borrowed-from-the-boys flair, it looks fab with androgynous accessories like a baseball cap, fanny pack and chunky white dad sneaks.

Get the look: Michael Michael Kors sneakers ($165; $99); Adidas sneakers ($100); City Chic dress ($119); Equipment dress ($325); See by Chloe sneakers ($335); Co dress ($595)

You might be thinking a giant dress paired with flat shoes is a one-way ticket to unflattering, but hear us out: While it’s not quite as refined as, say, a wrap dress, it’s sculptural and dramatic and so damn cool. Though most high-tops will do, we’re partial to a classic pair of black Converse, which feels so effortlessly stylish.

Get the look: Converse sneakers ($55); Vans sneakers ($65); Zara dress ($70); COS dress ($125); Stella McCartney sneakers ($395); Cecilie Bahnsen dress ($1,165)

Here’s an unexpected one: A fun way to style an ultrafeminine dress is to juxtapose it with clunky sneakers. Plus, it doubles the wears you’ll get out of a dress you might’ve been inclined to wear only in fancier settings. Just make sure to pay attention to minor details, because it’s the black trim on the sneaks that ties back to the black belt, making this outfit feel cohesive.

Get the look: Topshop sneakers ($60); All in Favor dress ($69); Puma sneakers ($110); Lost + Wander dress ($128); AFRM dress ($148); Balenciaga sneakers ($995)

OK, so you don’t have to opt for a slip dress in a bold color and a wild print, but the general idea stands: A slinky frock looks incredible with loud sneakers. Why? The two balance each other out. The minimal feel of the fabric on top is anchored by the sneakers, so you don’t look like a waif who will blow away in the wind. Plus, we love this vibrant color combo that’s totally individual and unexpected.

Get the look: Jessica Simpson sneakers ($89; $44); Anthropologie dress ($118); Universal Standard dress ($130); Reformation dress ($198); Sophia Webster sneakers ($275); Acne Studios sneakers ($550)