16 Dresses to Wear with Sneakers, Starting at Just $40

Your feet will thank you

Dresses are great and sneakers are even better, but combining the two might seem a little tricky. (You’re not trying to look like an extra in Working Girl, after all.) That’s why we searched the internet for incredibly chic suggestions for pairing your freshest kicks with an array of dress styles. Not only are sneakers a cute and casual way to elevate a dress, but they’re the more practical option, especially when you have plans to be out and about through the day. Whether you prefer a bodycon sweater dress or a flowy maxi, the key is finding the right pair of sneakers that go with your dress, and ideally, a pair that’s versatile enough to go with many different dress styles.

How to Style Sneakers with a Dress

The key to successfully wearing sneakers with a dress is that whatever your pairing may be, it looks intentional, and not like you ran out of the house in a rush without looking in the mirror.

If you’re on the petite side, you can opt for a mini dress with platform sneakers or a maxi with wedge sneakers if you’re looking for a little bit of height. (Heads up that a midi with sneakers might have a shortening effect.)

It’s also important to think about proportions and balance. For example, we like the idea of going for a bold, textured dress with more plain, streamlined sneakers or a basic dress with statement kicks. Pairing a bold dress with bold sneakers can be a little too much, whereas a simple dress with simple sneakers can feel a bit snoozy.

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Cutest Pleated Dress

1. Mare Mare Pleated Maxi Dress

Mare Mare

We’re big fans of the pleated skirt attached to the knit top for a cute spring look. Since this dress has a lot going on, we recommend pairing it with simple platform sneakers to complete your look and keep it casual. This dress is available in standard, petite and plus sizes and reviewers mention it runs quite big. “If you are not pregnant, absolutely order a size down because this fits me at seven months pregnant in my normal size. I also have a large bust and it's not constricting at all,” reports one customer.

Best Spaghetti Strap Dress

2. Lulus Party In Paris Midi


  • Why We Love It: high slit, tie spaghetti straps
  • Best Sneaker Pairing: Adidas Stan Smiths
  • Size Range: XS to XL

This sweet midi is a great example of a dress that looks fancier but can be easily dressed down with the right pair of sneakers. Our perfect pick? A pair of Adidas Stan Smiths. These classic shoes will add a sleek yet casual element to ensemble.

Top Linen Floral Dress

3. & Other Stories Linen Midi

& Other Stories

A floral dress is our love language. This adorable style has puff sleeves and a side slit to add some more movement and dimension. The linen material will be great for warm days since it’s so breathable. Throw on a chic pair of leather sneakers and you’ll stay comfortable and chic all summer long.

Most Functional Workout Dress

4. YPB sculptLUX Mini Dress

Abercrombie & Fitch

Whether you’re hitting the tennis court or going on a hot girl walk with some friends, this adorable activewear dress is made for movement. “[The] stretchy material makes it comfortable, and the slit is a great detail,” says one customer. “I will say, it’s more form-fitting than other athletic dresses (which I like) so if that is not your speed you might want to size up.” We recommend a cute pair of athletic sneakers to keep your feet supported while you sweat.

Cutest Ombre Dress

5. Raquel Allegra Slip Dress

Raquel Allegra

We can already see ourselves walking along the beach in this cute summery dress. When you hit the boardwalk, make sure to throw on a pair of platform sneakers to give you some height—go for a sleek, simple silhouette so you don’t take away from the breezy look. The dress is lightweight and reviewers say it’s very breathable.

Sleekest Collared Dress

6. Marea Midi Dress


  • Why We Love It: side tie, midi length
  • Best Sneaker Pairing: Veja V-12 Sneakers
  • Size Range: XS to XL

This office-appropriate dress is begging to be paired with a set of Veja V-12s. It has a feminine pattern and a tie-waist to accentuate your shape, plus a halfway button-down opening that stops at the waist and button sleeves, too.

Sweetest Flutter-Sleeve Dress

7. Madewell Flutter-Sleeve Mini Dress


Looking for a go-to dress option you can wear on repeat all summer long? Here she is. This frilly dress has flutter sleeves and flowy skirt, comes in black and golden yellow hues and is made of 100 percent cotton. Throw on some low tops with this dress, like these casual Converse.

Prettiest Slip Dress

8. Everlane The Satin Square-Neck Slip Dress


  • Why We Love It: lightweight fabric, square neckline
  • Best Sneaker Pairing: Puma Mayze Sneakers
  • Size Range: 00 to 16

We’re loving the clean-cut square neckline on this satin midi. It comes in three colors and has a button closure on the back. We would keep it cool and throw on a pair of chunky platforms with this dress (hint hint: these Pumas).

Cutest Petite Dress

9. J.Crew A-Line Linen Dress


A linen dress is a must-have in the spring and summer. This classic silhouette has darted cups and an empire waist. It comes in white, coastal sunset and black and is available in classic, petite and tall sizes. One self-described petite reviewer mentions the straps are a bit long on her, so you may need to have them altered if you’re on the shorter side. We’d wear platform sneakers with this dress, perhaps these from Crown Vintage.

Most Versatile Cotton Dress

10. Quince Tencel Rib Sleeveless Dress


We love a basic knit dress like this one because it’s easy for layering and is super comfortable. It’s made of a soft Tencel fabric (hello, eco-friendly) and has a ribbed texture. There’s a short slit in the back of the dress for some movement, which means a pair of pink platforms will add some flair to this look.

Comfiest Ribbed Dress

11. Free People One Natasha Sleeveless Midi

Free People

A unique dress like this deserves to be the star of the show, and we love how the model is styled with a cute pair of high-tops. From the mock neckline to the ribbed, worn-in looking fabric to the cinched waist, this maxi is a great pick for casual outings, and comes in five colors. “This dress is beautiful and [is] high-quality material. It is very forgiving. I am a size 10/36DD and the large fit perfectly and not too tight. I bought it in the aquamarine color and it will be perfect for spring,” says one reviewer.

Most Sophisticated Shirt Dress

12. Maeve The Soren Dress


  • Why We Love It: midi length, button-down
  • Best Sneaker Pairing: New Balance 327 Sneakers
  • Size Range: XXS to XXL, standard, petite, plus

Which way’s the beach? We can’t wait to wear this on the coast with a pair of bold sneakers, for a fun pop of color. The dress buttons all the way to the bottom, comes in seven color options and is made of cotton.

Top Activewear Dress

13. Playground Active Sunday Dress

Free People

The summery shades of this color blocked dress have us excited for outdoor workouts when it warms up outside. This dress has a lightweight, cotton-like material according to one reviewer. “The fit is a little longer and very true to size—such a great dress for spring and summer! Also, love that buying it supports a local biz owner,” she says. Wear yours with your favorite workout sneakers or a sleek pair of white tennis shoes.

Prettiest Print

14. Mango Printed Dress


This casual dress will look great with simple platform sneakers like these from Sam Edelman. The high slit adds a bit of sexiness to this basic silhouette and the black floral print is great if you like florals but don’t want it to look too feminine.

Cutest Denim Dress

15. Reformation Cecil Denim Dress


Want something a little more unique? Go for a denim babydoll dress. This darling option has an empire waist, a pleated skirt and a back zipper closure. A set of chunky platforms will be the cherry on top of this cute look.

Breeziest Linen-Blend Dress

16. Abercrombie & Fitch Linen-Blend Mini Dress

Abercrombie & Fitch

The breathability of this linen dress will have you wanting to wear it from now until fall. Juxtapose the sleek vibes with a comfy dad shoe and you’re ready for brunch, sightseeing and everything in between.

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