How to Wear Sneakers With a Dress

Paxton Slip On in Cobblestone shown.

If you’re over the fashion trends that trade comfort for looks, you’re going to love this one: sneakers—but with dresses.

Far from the days of saving your sneakers for the gym, we now live in a world where your comfiest, most supportive sustainable shoes are making leaps and bounds when it comes to style and design—and with looks so fresh, it seems silly to leave them in the locker room. Instead, trendsetters are pairing sneakers with dresses for an easy, comfortable, and chic outfit that will keep you fashionable and fancy-free all day long.

Those who instinctively reach for a pair of heels, sandals, or flats when dressing up may be perplexed on how to wear sneakers with a dress. If this is you, fear not: We’ve prepared a full spectrum of ideas to get you started on the right foot. 

Why Wear Sneakers?

Let’s get one thing out of the way: if the word sneakers brings to mind a drab, clunky pair of white gym shoes, a whole new world of possibilities awaits you. The concept of sneakers has expanded to include a whole range of stylish, versatile options.

To name a few, these include:

  • Slip on sneakers
  • Platform sneakers
  • Classic court sneakers 
  • Wedge sneakers
  • Lined sneakers

What’s more, choosing sneakers as compared to high heels (long viewed as the most fashionable shoe to pair with a dress) could even benefit your health. Studies have shown that wearing high heels is associated with various aches, pains, and injuries, some of which could leave you with long-term effects.

Some researchers even found that long-term use of high heels actually changes the muscle fibers and tendons in your legs for the worse. And of course, you’ve probably experienced the blisters, arch pain, and twisted ankles that can result from high heels, sandals, flats, and other dressier options.

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Comfort and Style: How to Pair Sneakers With Dresses Like a Pro

We’re here to tell you, it doesn’t have to be this way. You can have both style and comfort. If you’re still struggling to picture it, stay with us: We’re about to break down our favorite sneaker-dress combos.

#1 Wear It As a Classic Look

Not sure how to style white sneakers? Nothing is more versatile than a classic white court sneaker. These are your go-to, no-brainer option for any outfit. 

White sneakers go well with a classic knee-length dress and denim jacket for casual, comfortable style. For a clean, crisp look that elongates your legs as well as any heel, pair your sneakers with no-show socks and a dress that hits just above the knee.

However, if your outfit features a dress with bright and powerful patterns or a bold cut, a classic white sneaker can also be an ideal option if you want to avoid overshadowing the rest of your fit. Sometimes, you simply need to give your upper half some room to shine.

All in all, this is an option you can’t get wrong. And as an added bonus, your feet will feel oh-so-comfortable while you’re rocking them. All that’s left is to lace them up, and you’re out the door. Pro tip: Be sure to check out our latest blog on How to Clean White Shoes to ensure you’re keeping your white kicks fresh and clean!

#2 Create Contrast

The idea of pairing a sporty sneaker with a dress might seem counterintuitive, but we love the idea of complementing a flowy, feminine dress with something that adds an edge of contrast. Whether you’re looking to make a statement or just want to try something new, the right pair of sneakers can add an easy, but unexpected twist to your style.

There are many ways to play with contrasting styles, depending on how much of a fashion risk-taker you are. Lucky for you, we’ve thought ahead with a few ideas for the subtlest to the showiest of fashionistas to add some contrast.

  • Try pairing a dress with a bit of movement, like an A-line or wrap dress, with a sporty sneaker that features more angular lines or an athletic look.
  • Pull off this look with a flowy, full-length maxi dress to keep you warm in cooler temperatures.
  • For extra style points, use contrasting patterns, ruffles, and colors, such as a floral motif, to contrast with your cool, confident choice of shoes. 

Forget those who say you can’t have the best of both worlds. This style is the embodiment of having it all.

#3 Rock It With High Socks

For those who love coordinating colors, adding socks to your look can contribute an extra layer of intrigue. While no-show socks are an ideal option for those who like to keep things hidden, they’re not the only way to go. 

Try pairing your dress-and-sneaker combo with socks of different heights, colors, and patterns. A flash of bright neon above your ankle can lighten up an otherwise monotonous color palette, while simultaneously keeping your feet extra comfortable.

Socks can also elevate your sneakers-and-dress look. Tall socks that hit at or above the knee pair well with a mini dress in the fall or winter, giving you both the coverage, style, and flirty fashion of tall boots with the versatility and comfort of a sneaker. 

Resident in Grey shown.

#4 Heighten Your Style

If you find it hard to part with the added height your heels can offer, sneakers could still be a seamless replacement. After all, the higher the heels you wear, the more likely you are to deal with difficulties related to posture, balance, and gait. 

Meanwhile, you could get the same leg-elongating, height-enhancing benefits from a pair of wedge sneakers, which still give you that classic heel-toe lift without requiring you to balance on the head of a pin. 

Wedge sneakers are perfect for those looking to add comfort to a more polished, wear-to-work look, such as a pencil skirt or sheath dress, but really, these would be a knockout look with just about any option.

#5 Add Some Lift 

If you simply want to rise above the rest, but also appreciate the chunky heel of a boot, a pair of platform sneakers could be the way to go. Compared to a wedge heel, platform sneakers offer a more laid-back look, while still giving you an inch or two of extra height.

These sneakers are a clever way to add a bit of unexpected glam to a more casual style, like a cotton sundress or a T-shirt dress. In a neutral color, a pair of slip on platform sneakers also pair well with a modern look. Try them with a sleeveless mid-length linen dress for the ultimate duo of practical, utilitarian comfort and chic contemporary style.

#6 Pop In Some Color

A pair of bright, bold sneakers could be just the thing to amplify your look. If you’re not quite sure how to pair your high-chroma kicks with a dress, allow us to lead the way:

  • White on neutrals – Wear them with a classic, neutral-toned dress as a preppy but subtle lift of color.
  • Keep it colorful – Coordinate your bright sneakers with a dress and accessories in variations of the same color to appear simply prismatic.
  • Bright and bold – If you’re ready to wear them loud and proud, wear them with a dress in any other bright, bold color to turn some heads in the best way possible.

#7 Stay Warm (and Stylish)

Of course, one of the downfalls of wearing a dress is that exposing your legs means exposing them to the elements and icy temperatures of winter months. And though heels and flats may cover your toes, they do little to keep you cozy when the thermometer drops below freezing.

Adding a layer of leggings or tights under your dress is one way to keep your dresses from spending the winter collecting dust in your closet. To finish off this outfit, add a pair of faux fur-lined sneakers to stay extra snug no matter what the weather brings.

#8 Feel Fresh

If you’re the type to pack up your dressier, but less comfortable work shoes and wear sneakers on your commute, only to slip the heels back on right before you walk in the door, you know the feeling of regret that comes with leaving that cloudlike comfort behind.

But if all the wardrobe changes have you feeling flustered, let us save you a step. When you intentionally style your sneakers with a dress, you’re ready to walk on in.

If, however, you still need the ease of sliding on a fresh change of footwear, slip on sneakers are the way to go. These lightweight kicks have all the effortlessness of a flat with the support of a sneaker, meaning you’ll feel easy, breezy, and cool from the moment the sun rises. To stay extra fresh in the warmer months, pair these with a button-up shirt dress for an elevated yet casual style.

Stay Fashion-Forward and Foot-Friendly with TOMS

Feeling inspired to try wearing a dress with sneakers? We’ve got you covered. TOMS offers a range of sneakers for women that will keep your fit fancy while also providing worlds of comfort.

While our range of sneakers will have you ready to take on any style persona, our OrthoLite® insoles mean you won’t have to sacrifice comfort and support.

Who knew breaking the boundaries of fashion could feel so empowering? When you’re ready to style your one-of-a-kind look, start with TOMS.

Sources: 

PubMed. High-heeled shoes and musculoskeletal injuries: a narrative systematic review.

https://pubmed.ncbi.nlm.nih.gov/26769789/

TIME. You Asked: Do High Heels Actually Damage My Feet?

https://time.com/3847330/you-asked-do-high-heels-actually-damage-my-feet

Journal of Physical Therapy Science. The influence of high heeled shoes on balance ability and walking in healthy women.

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6047962/

Reviewed By Dan Caves

Dan Caves is the Senior Manager of Digital Marketing at TOMS and has been operating in the digital space for 6 years, writing about the latest trends or styles and helping brands make bold statements with innovative tactics and creative concepts. He's determined to go all the places, see all the things, and pet all the dogs.