10 Dresses To Pair With Sneakers This Spring and Summer, As You Ease Out of Sweatpants

Photo: Getty/ Manuel De Los Reyes Rubio / EyeEm
For most of 2020, I couldn't imagine a time when I'd ever want to return to "real" (read: not soft) clothes. But now that I'm vaccinated and can socialize safely outside of my tiny quarantine bubble, I'm suddenly very into playing dress-up. With that said, I'm not fully ready to throw on three-inch heels again, nor is there really an occasion to do so in a world still limited by COVID-19 precautions, where the best socializing takes place outdoors. So this summer, I'll be living in dresses paired with sneakers, the perfect pandemic-transition outfit.

Pulling this look off as intended, however, can be a bit tricky. Below, find styling tips as well as 10 dresses that play well with sneaks.

Experts In This Article
  • Chelsea Von Mach, Chelsea Von Mach is an LA-based stylist and vintage boutique owner.
  • Nicole Pollard Bayme, Nicole Pollard Bayme is the founder of Los Angeles-based fashion styling firm, Lalaluxe.

How to style dresses with sneakers, according to stylists

Sneakers work well with mini, midi, and maxi dresses hitting at the ankle, says Nicole Pollard Bayme, founder of Los Angeles-based fashion styling firm, Lalaluxe. "If you pair them with knee-length dresses, however, they tend to shorten the leg. And floor-dusting maxis tend to get in the way of sneakers."

When trying to pull a combo together, Bayme says it's important to keep balance in mind. "Pair frilly dresses from brands like Love Shack Fancy with rubber combat boot sneakers or sporty Stan Smiths," she says. "Pair a monochromatic look—think black maxi tank dress from brands like Helmut Lang and The Row—with a neon pop of color, and pair a vintage dress with a designer sneaker for a high-low look."

She caveats, however, that what you're looking for is contrast, not competition. LA-based stylist and vintage boutique owner Chelsea Von Mach agrees, and also notes that it's important not to overdo it. "Your sneakers should be cohesive with what you’re wearing without looking like you're trying too hard or like you could go play rugby in them at the same time," she says. "Don’t go over the top and wear soccer cleats with a gown. I don’t think that’s a vibe—it’s just goofy."

To make the look cohesive, Bayme then recommends selecting accessories (like a bag, a jacket, a sweater) that help create a visual story so the sneakers look is thoughtful and not out of place. "Pairing your sneaker and dress ensemble with the appropriate bag is important," she says. "Go for something that solidifies the playful look like a mini backpack, waist bag, or nylon shoulder bag. I would not do an evening clutch with a floral maxi dress and sneakers, or the shoes would look out of place."

And with all that said, Von Mach notes that it's difficult to give universal advice on how to make this look work, as a person's height and body shape come into play, as do prints and fabrics and colors. So, she says, it's important to play around to see what works for you. "Use your own style mood board as a road map, and do your own style homework, then create your own version of sneakers and dresses," she says. "If something speaks to you and you don’t know why, go in that direction. Be bold. Buy the neon orange sneaker or the floral print one, just make it you!"

Shop dresses to pair with sneakers

shrimps-gingham dress
Photo: FarFetch
Shrimps Rafferty Off-Shoulder Gingham Midi Dress — $440.00

Got a gleaming pair of white sneaks ready to hit the road? They’d pair perfectly with this gingham midi creation for an urban picnic, sunny Saturday brunch, or really any type of day date.

Photo: Reformation
Reformation Marlowe Dress — $98.00

When it comes to sneaker-perfect dresses, it’d be difficult to outdo a leopard-print slip dress. Slinky and sexy, this style might be too much without sneakers, which means it’s usually pitch-perfect when styled with them. And in its own way, leopard is a fairly neutral print, which means it’ll pair well with a wide range of options.

Photo: Staud
Staud Edesia Dress — $325.00

As Bayme notes, this midi tank silhouette would be fun to pair with a pair of neon sneaks for a pop of color.

Photo: Everlane
Everlane the Shirred Mini Dress — $78.00

This is an easy-breezy dress that’ll pair well with sportier kicks, for contrast, or with floral sneakers to keep the vibe soft.

Photo: Staud
Staud Mini Elio Dress — $243.00

While partnering with this color way way can be tricky, it’s not impossible; and if you like the silhouette but tangerine isn’t your thing, this adorable cold-shoulder frock does come in other hues (including low maintenance black).

Photo: Nordstrom
Faithfull the Brand Eldora Mini Dress Bendita Floral Print — $189.00

This feminine look pairs well with sportier sneakers for eye-catching contrast that looks intentional but not overwrought.

Good American '90s Ribbed Tank Dress — $99.00

While paired here with heels, this ribbed black midi could pair seamlessly with sneakers and a jean jacket.

Photo: Leigh NYC
Leigh New York Paige Midi Dress — $350.00

Because slip dresses are ideal for partnering with sneakers, here’s another option. This made-to-order midi version is more or less a blank slate, which means just about anything goes south of the ankles; given the length, however, you might want to stick to low-tops to complete the look.

Photo: LoveShackFancy
LoveShackFancy Citra Midi Dress — $225.00

Even though this print is a little busy, because the silhouette is simple you can still have some fun with sneaker pairings and in this case, it might actually be best to eschew an obvious white option in favor of something with a little more pizazz. You can go fully opposite in terms of color way and print or try something in the same highlighter pink—a highlighter yellow could look cute, too.

Photo: Madewell
Lemlem Halima Mini Smock Sundress — $345.00

The sweetness of this tie-shoulder silhouette is offset by the edgy blue animal print, which Lelem founder and Ethiopian supermodel Liya Kebede says was inspired by the big cats of sub-Saharan Africa. Pair it with another animal print to make a statement, or stick to your basic whites for a more understated look.

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