The Dos and Don’ts of Wearing Sneakers with Dresses

Dresses and sneakers: two very different styles, right? But when done correctly, the feminine and masculine styles can create a totally on-trend look. With fall in sight, last spring’s hot dresses with sneakers trend is set to make a return. We consulted Michelle Kelchak, Keds‘ Design Director, for some styling tips so you can make this tricky trend a fashion “do.”

Do consider the season and fabric of your dress.

Choosing the perfect pair of sneakers for your dress depends a lot on the style of the dress you’re wearing and what time of year it is. “For example, if it’s summer and your dress is made of a lightweight fabric, chose a lightweight material for your shoes, such as canvas or eyelet. If it’s fall and your dress is made of wool, pair it with suede or patent leather sneakers,” Kelchak says.

Do have fun experimenting with prints and colors.

Mixing prints can be a tricky fashion feat, but it’s a great way to show off your sense of style. Some fun ways to incorporate this idea into your dresses/sneakers experiment? Kelchak suggests rocking a pair of polka dot sneakers with a striped dress. Or, if florals are more your thing, pair your large print floral dress with a sneaker with a small flower print. Just make sure both prints share a similar color; that’s the key!

Don’t go to the extreme. 

A melange of masculine and feminine is always a fun fashion twist, but Kelchak cautions us against taking things too far: “Sometimes mixing masculine and feminine trends works, but it can be tricky, so oxfords are always a safe bet. But never wear a feminine frilly dress and a pair of athletic sneakers. NEVER!” 

Don’t forget proportions. 

The goal of dressing is always to accentuate your best features, right? Right. So avoid instances where wearing sneakers will visually cut off your legs. Keep proportions in mind! “Never wear high tops with a knee length skirt. That will make your legs look short. Oxford sneakers like Keds will elongate your legs, making the proportions of your outfit look much better,” Kelchak says.

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