‘I’m a Stylist & These Are the Only Sneakers You Should Be Wearing With Dresses’

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Sneakers have a way of turning any outfit into an effortless ensemble—and that is especially true when paired with more traditionally dressy pieces. If you want to create a casual yet put-together look this spring and summer, a pair of comfortable sneakers and your favorite mini or midi dress can do the trick. As a comfort-first girly myself, I am obsessed with wearing sneakers with dresses and skirts, especially when I know I will walk a lot throughout the day. (Aching feet after a full day of wearing sandals? No thanks.)

Ahead, I tap a celebrity stylist for some tips and tricks for making the sneakers and dresses look as effortless as it appears, plus share some of the best sneakers to wear with dresses, including some of my tried-and-true favorites. 

Best Sneakers to Wear With Dresses at a Glance

• Best Overall: Puma Suede Classic, $90
• Most Versatile: Veja V-90 Leather Sneaker, $180
• Best Mesh: Sam Edelman Irma Low Top Sneaker, $100
• Best for Spring: Adidas Sambae x Liberty London Shoes, $115
• Best Athletic: New Balance 9060 Sneakers, $150
• Best Machine-Washable: Rothy’s The Court Sneaker, $149
• Best Leopard Print Sneaker: HeyDude Hudson Lift Luxe, $80 (was $90) 
• Best Skate Shoe: Levi’s Drive Lo 2 Sneaker, $33 (was $60)
• Best Retro Sneaker: Reebok Club C 85 Vintage , $57+ (was $85)
• Best White Sneaker: Cariuma Salvas, $139
• Best Metallic Sneaker: Keds Triple Kick Metallic Leather Lace Up, $60 (was $75)
• Best Ballet Sneakers: Vivaia Square-Toe Lace-Up Satin Sneakerina, $129

How to Style Sneakers With a Dress, According to a Stylist 

“When styling dresses with sneakers, be mindful of either coordinating the sneaker with the vibe of the dress or going for maximum contrast and juxtaposition,” says celebrity stylist Samantha Brown. 

There are several ways to style sneakers with a dress, and Brown says to first consider your dress length. “Sneakers work best with short hemlines to a midi length,” she explains. “Maxi dresses tend to get clunky, and it’s more flattering to show some leg.” 

Color can also play a major role when styling sneakers with dresses. According to Brown, you can lean on white and metallic sneakers as more neutral options and then use bright color pops, animal prints, and other funky details to help create visual interest. She also says to be mindful of your sock choice. “Make sure the socks are also intentional,” she notes.

Best Types of Sneakers to Wear With Dresses

Sneakers might not seem like the obvious shoe choice for dresses, but the contrast can help create a more laid-back and relaxed look and also provide an opportunity for a more comfortable—yet still very stylish—ensemble. “Right now, there is something for everyone from vintage-inspired sneakers to more athletic ones, and even ballet sneakers are having a moment,” Brown notes. She adds that this isn’t a trend to take too seriously and recommends playing around and having fun with some experimentation. “When in doubt, opt for a more neutral pairing and stick with a classic, non-athletic sneaker to keep the look toned down,” Brown adds. 

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Best Sneakers to Wear With Dresses