Ask MSL | How to Wear Sneakers with a Dress

Q: I’d love to be able to wear my sneakers with a dress, but I’m not sure I can pull it off… is it just for 20-somethings? — Amy P. 

You see it all the time… influencers and models stepping out in their designer sneakers paired with a cute mini or flowy dress. Or, on the runways we’ve seen super chunky sneakers the likes of Gucci and Balenciaga, as of late. Making this look work for you is all about the style of sneaker. While some ladies can pull off the chunky-sole sneaks and own it with attitude, the rest of us feel a little too “Melanie Griffith in Working Girl” — if you’re nodding you may or may not have grown up in the ’80s and totally get this reference. Okay, so what to do? You can absolutely wear sneakers with a dress or skirt. They generally look best with a flared skirt style — mini to midi, not pencil or fitted dress skirts. Although, sneakers will work with just about any style of t-shirt or casual dress. Just don’t try to wear this look to the office, unless you work in a creative industry or at high-tech company where almost anything goes. Here are some sneaks – from affordable to designer – that will easily pair well with a dress and a dose of confidence.

Dress, Reformation // Shoes, Converse

Dress, Faithfull the Brand // Shoes, Sam Edelman (on sale!)

Dress, Altuzarra // Shoes, Veja

Dress, Michael Kors // Shoes, Golden Goose