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How to Wear Dresses and Skirts with Sneakers and Not Feel Frumpy

Slipping on a pair of sneakers with a dress doesn’t have to mean compromising style for comfort.

By Madeleine Kim

It’s a question we hear often: What’s the secret to wearing dresses and skirts with sneakers without looking frumpy? When done right, a dress with sneakers is the epitome of casual-chic. It’s making an effort without trying too hard and dressing up without sacrificing comfort. 

But if you’re new to the pairing, it can feel intimidating. Luckily, I’d argue that to really nail it, you only need two things: the right pair of sneakers and a healthy dose of confidence. As for the shoes? That part is easy. We partnered with our favorite sneaker brand, Koio, to create the perfect pair of sneakers, and we have yet to find a dress or skirt that doesn’t look great with them. And the confidence? I have a feeling you’ve already got that part covered. 

Here are a few chic-yet-accessible looks to try out, modeled by M.M. employees Melissa, Taylor, and Amanda.

Opt for Coordinating Separates

Try tucking a fitted knit top, like the Louisa, into a high-waisted skirt, like the Orchard. The variation in texture adds dimension to your look, while the tucked-in top helps define your waist. Vibrant colors and patterns paired with white sneakers can also help give your outfit that fresh feeling—bright, playful, and not at all frumpy. Big earrings complete this easy-yet-elegant look.

Try a Tonal Look

When in doubt, go for a tonal look—an outfit composed of pieces in the same color or similar colors. A tonal look is always chic, and it’s incredibly easy to put together. The Lou dress in dusty pink is a beautiful match for the Koio sneakers in azalea; both shades of pink feel like summer, but they’re subtle enough that you can wear them multiple times per week.

Keep It Short and Sweet

If you’re used to wearing your dresses and skirts with heels and feel daunted by the switch to sneakers, there’s an easy solution: Pair your sneakers with pieces that have shorter hemlines—above the knee or higher. Shorter dresses tend to look more casual (especially if they have a T-shirt silhouette, like the Maaza), which will make your sneakers feel right at home in the outfit. Complete the look with a better-than-denim jacket, your favorite hoops, and sunglasses.

Madeleine Kim

Written By

Madeleine Kim

Madeleine Kim is a Brand Manager at M.M.LaFleur, where she started out as a stylist. She loves developing styling-focused content and creating newsletters that bring the M.M. community together.

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