Outfits with a Dress & Sneakers

The older I get, the more I prioritize comfort, but that doesn’t mean I’m giving up on style. And one combo that’s been in heavy rotation the last few years? Dresses and sneakers. It’s and easy and practical pairing and works for everything from running errands to casual dinners. If you’ve ever felt like sneakers don’t “go” with a dress, I promise: they do. You just need the right pairing. Here are a few easy, wearable outfits with a dress and sneakers. No trend-chasing or uncomfortable shoes required.

Best Dress with Sneakers Ideas

With a Maxi Dress

A maxi dress paired with low-profile sneakers gives off a relaxed, effortless vibe. Go for a solid-color or tiered maxi, and wear it with classic white canvas sneakers or slip-ons.

outfits with a dress and sneakers
outfits with a dress and sneakers

With a Slipdress

Slipdresses don’t have to be reserved for date night or for the office. It’s a subtle mix of dressy and casual that makes your outfit feel intentional without trying too hard.

how to wear sneakers with a dress
slip dress and sneakers outfit

With a Ruched Dress

A ruched dress adds shape without feeling too tight or formal. I like pairing this style with sporty sneakers to tone it down a bit.

ruched dress and sneakers outfit

With a Wrap Dress

A wrap dress is universally flattering, and pairing it with sneakers adds a relaxed edge.

outfits with a dress and sneakers
spring style tips

With a Sundress

Think light cotton or linen dresses that are simple, breezy, and made for summer. Pair your sundress with casual white sneakers or even colorful retro styles to keep the look grounded.

target red sundress outfit
how to wear a dress with sneakers

With a Flirty Dress

Ruffles, puff sleeves, or a little twirl-worthy skirt? Don’t overthink it. Let the dress do the talking and ground it with solid sneakers.

ruffled dress and sneakers
flirty dress and sneakers

With an Athletic Dress

Pair with fashion or running sneakers. It’s a great casual weekend outfit.

outfits with sneakers and a dress

With a T-Shirt Dress

A t-shirt dress and sneakers is probably the most low-maintenance outfit on this list. You can keep it super simple with white leather sneakers, or add a pop of color in your shoes or accessories.

cute dress and sneakers outfit
outfits with dresses and sneakers

With a Knit Dress

Knit dresses are cozy and a great match for chunkier sneakers or platform styles. If your knit dress is body-hugging, balance it with high-top sneakers. If it’s more relaxed, go sleek on the shoes.

how to wear a dress with sneakers

With a Midi Dress

An outfit with a midi dresses and sneakers are one of my favorite pairings for casual workwear. This combo looks polished even with the sneakers.

With an A-Line Dress

A-line dresses are timeless for a reason, they’re flattering, easy to wear, and work with just about any shoe. When styled with sneakers, the look becomes casual without losing its shape.

outfits with a dress and sneakers
outfits with a dress and sneakers

With a chambray dress

A chambray dress and sneakers is an outfit that always works, no matter what you have planned.

Target denim dress

I hope these outfits with a dress and sneakers inspired you to try this combo! It’s all about finding that sweet spot between comfort and personal style. Whether you’re heading out for the day or just want to feel put together without overthinking it, this pairing works. Start with what you already have, and see what feels right. It’s an easy style update that doesn’t require buying a whole new wardrobe, just a fresh perspective.

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Other posts you might like:

Classic Outfit Combo that Always Works

Floral Wrap Style Maxi Dress

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dress and trainers outfit

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Between Naps on the Porch | I do de Claire | Walking in Memphis in High Heels & The Fashion Canvas | My Slices of Life | The Style Splash |  Curated by Jennifer | Mummabstylish | Shelbee On the Edge | Nancy’s Fashion Style | Momfessionals | Marsha in the Middle 


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10 responses

  1. A winning combination. I find the biggest worry is not knowing which sneakers are considered "over"!

  2. Kellyann

    Just like you I am all in for comfort without sacrificing style! We have so many great sneaker options now and I just love the way they pair with dresses. Great inspo Jill!
    xo,
    Kellyann

  3. So many chic sneakers and dress combos! I adore that striped sweater dress especially. Thanks for the link up!

    https://www.kathrineeldridge.com

  4. Living on Cloud Nine

    I will forever wear this combo! You look so darling in each and every look!

  5. So many cute styles! I really need to up my sneaker game. I think I have 2 pairs.

  6. Mireille

    When in doubt, add a pair of cute sneakers! I wore mostly dresses for holy week and added sneakers most days. I love having a variety of them. All of these outfits are so cute and fun!
    http://www.chezmireillefashiontravelmom.com

  7. Talk about great inspiration. Goes to show they work with every type of dress.
    XOXOX
    Jodie

  8. I love all of these looks, Jill! They make me excited for warmer weather. Thank you for sharing, and I hope that you are having a great day so far!

  9. I'm glad you show this variety of dresses with sneakers. Because I just bought pink ones and I'm loving this style a lot. Indeed comfortable, but so stylish!

  10. Both of those sundresses are just super cute on you and love the sneaks!

    Carrie
    curlycraftymom.com