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Photo: Katie Friedman

How do I wear sneakers and a dress without looking too young?

A: Finally, it’s warm enough that a question about dresses can be asked. How joyous! Personally, I love the combination of sneakers and dresses. The pairing helps keep things casual when you may feel overly girly. However, I do understand the worry that the look can feel very young. I try to avoid this by keeping the length of my dresses on the longer side: A midi-dress is the perfect length to wear with sneakers. While a short dress might make you feel a little high school, a longer dress will give you some sophistication points.

Today I’m wearing a vintage dress that I picked up during my trip to Australia, a striped oxford from the now defunct Rugby by Ralph Lauren line (R.I.P), and classic white Vans sneakers. Now, you may remember that I have quite an affinity for Stan Smith kicks, but they’re leather and warmer weather really calls for a canvas shoe. I do like to change it up every now and again.

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To replicate this look, I would suggest avoiding a dress that’s too short or poufy. Keep the silhouette simple and streamlined, yet still feminine. Another trick: Including some masculine touches—like layering a button down shirt—add an element of surprise that takes some of the focus off the fact that you’re wearing sneakers with a dress.