How to Work Sneakers with Your Favorite Dresses (& Skirts)

While jeans are the ride-or-die go-to, dresses automatically look way more considered, giving some sartorial oomph to your day and making even the mundane feel special. But what if you’re headed to brunch and it’s a hike? Or you have to make it across town via 2.5 modes of public transportation? What if you’re just going to the grocery store, but dammit you want to wear a dress? Utilitarian isn’t a word normally associated with dresses (or skirts)—they can have a prissy reputation for sure—but that’s where sneakers come in. The high-low mix of pairing a dress with sneaks is fresh, unexpected, and ultra attention-grabbing. It’s like a second life for your favorite lady-ish looks. Cop some new styling ideas below.

Photo by @kikidagawd

Prep School

We’re taking back the uniform with an updated version of school-girl staples—and this time you won’t land in detention for blowing the dress code. If you’ve done your homework, you know that the most interesting outfits score an A+ for the mix, however subtle: Worn-in sneakers offset a preppy button-down shirt and kicky A-line skirt (as short as you want), and a pair of sheer, patterned anklet socks is like finishing school for your look.

Photo by @annabelle.sadler

Shirt, Shoes, Party

A stylish shirtdress is what we like to call an instant look; throw one on and you’re pretty much good to go. All that’s left is the shoes. When you’re working with a multi-colored frock, pick one shade and bring it to life on your feet with a pair of Chuck Taylors, which come in a rainbow-worthy range.

Photo by Noah Sahady

Skorting the Issue

With its throwback vibes (who didn’t own one back in the day?), we predict that this will be the year of the skort (skirt + shorts, if somehow you missed out on this most major of fashion moments). An ultra-short skort gives you ample chance to show off some leg—and a pair of classics. Anything low-slung and low-profile is the play: Puma Suedes, Vans Old-Skools, or Keds.

Photo by @sirius.film

Long Story

Tone down the formal feel of a floor-grazing maxidress with a sneaker in a similar shade. The result? A mix that’s dramatic, but still laid back.

Photo by Lucka Ngo

Mid Range

Midi-length dresses and high-top sneakers were made to be BFFs. A pair of Chucks (Vans Sk8-His would work too) give some much-needed edge to an otherwise modest look—a great way to update those oversize thrift-store shifts you just can’t stop buying. A cool jacket—jean, suede, leather—helps too.

Photo by Tory Rust

Color Coordinated

Rather than letting your shoes be an afterthought, start there and let them shape your outfit. Taking color inspo from a pair of Adidas Superstars results in a graphic black-and-white getup mixing patterns (stars and stripes) and materials.

Photo by @carssun

Short & Sweet

A body-hugging silhouette, high hemline, and off-the-shoulder sleeves would be too “too” with a pair of heels—at least for daytime hangs. But high-top Vans lend a cool feel that’s relaxed and sooo SoCal it’s board-worthy.

Photo by Alie Layus

Check, Check, Check

A genius hack for elongating your legs and keeping comfortable? Go for a leg-baring mini and low-cut pair of sneakers like these Vans Authentics that hits below your ankle. Together, the two make your stems look extra lengthy.

Photo by Jana Carrero

Back to Basics

A simple dress that’s nipped at the waist creates a figure-flattering silhouette, while its single shade ensures that all eyes will be on your footwear. Make sure they’re up to the attention by opting for a chunky, substantial pair—New Balances, Sauconys, Reeboks.

Photo by Alie Layus

Layer Layer Pants on Fire

Layering keeps a look interesting from your head (think a simple slip dress over a vintage T, under your favorite jean jacket) to your toes (folded socks and a classic pair of high-top Chucks).

Photo by @nowonvoyage

Monochrome Magic

The introduction of sneakers can bring an out-of-bounds outfit back down to earth, like a monochrome look built around one super hue—like stoplight red. The trick here is playing with texture: a short skirt in a pattern and a graphic tee keep things interesting.