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Best Dresses to Wear With Sneakers 2021

25 Dresses That’ll Complement Your Favourite Sneakers Better Than Pumpkin Spice Does Latte

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Dresses and sneakers are one of those combos that go together like peanut butter and jelly. Great on their own but even better together, and timeless in their appeal. Plus, since there have been fewer occasion to sport heels — or proper shoes — in the last year and a half, trainers have seen a lot of play, and it's hard to give up that cushioned comfort when heading out.

To inspire some new outfits this season, we searched for the best pieces to match up with your favourite sneakers like including minis (and high-tops), midis (plus slip-ons), and maxis (with classic canvas). Whether your shoe preference is white, black, or something more colourful, there's a style here to inspire your next combination. First, think about your preferred pairs and then check out our 25 dress picks starting at $35 ahead.

Image Source: Old Navy

Old Navy Waist-Defined Striped Tie-Belt Midi Wrap Dress

Both the blue and khaki version of this Old Navy Waist-Defined Striped Tie-Belt Midi Wrap Dress ($45) would be oh-so-pretty with a classic pair of canvas sneakers.

Image Source: oldnavy.gap.com
Old Navy Waist-Defined Striped Tie-Belt Midi Wrap Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Ruffled Tie-Neck Chambray Swing Dress

There's just something that always catches our eye when it comes to a mini coupled up with high-tops, and this Old Navy Ruffled Tie-Neck Chambray Swing Dress ($45) look is no exception.

Image Source: oldnavy.gap.com
Old Navy Ruffled Tie-Neck Chambray Swing Dress
$45
from oldnavy.gap.com
Buy Now

Alo Yoga Cityscape Sweatshirt Dress

While the belt on the Alo Yoga Cityscape Sweatshirt Dress ($118) can be removed, it's an extra sporty accessory to your favourite running shoes while running all around town.

Image Source: aloyoga.com
Alo Yoga Cityscape Sweatshirt Dress
$118
from aloyoga.com
Buy Now

Old Navy Long-Sleeve Fit and Flare Slub-Knit Midi Dress

No matter which of the three fall-appropriate colours you choose (between cranberry, pumpkin, and leaf), an Old Navy Long-Sleeve Fit and Flare Slub-Knit Midi Dress ($40) and slip-on sneakers equal one solid choice to trek through apple orchards this season.

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Fit and Flare Slub-Knit Midi Dress
$40
from oldnavy.gap.com
Buy Now

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Old Navy Smocked-Waist Fit and Flare Cami Midi Dress

When you're heading to a party but you're not sure your feet can take a full night of heels, don't miss how cute this Old Navy Smocked-Waist Fit and Flare Cami Midi Dress ($45) looks with comfy sneakers as well.

Image Source: oldnavy.gap.com
Old Navy Smocked-Waist Fit and Flare Cami Midi Dress
$45
from oldnavy.gap.com
Buy Now

Superdown Ashanti Backless Dress

We especially like this fitted Superdown Ashanti Backless Dress ($45, originally $64) with a chunky dad sneaker or pair of Air Force 1s for fall.

Image Source: revolve.com
Superdown Ashanti Backless Dress
$45
from revolve.com
Buy Now

Old Navy Long-Sleeve Floral-Print Poet Mini Swing Dress

If you love a matching moment, grab creamy or shades-of-blue sneakers to wear with this Old Navy Long-Sleeve Floral-Print Poet Mini Swing Dress ($45) ASAP.

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Floral-Print Poet Mini Swing Dress
$45
from oldnavy.gap.com
Buy Now

Athleta Marlow Maxi Dress

The Athleta Marlow Maxi Dress ($108) would be especially nice on the plane and on holiday since cushioned sneakers look and feel great as you walk the town or the terminal.

Image Source: athleta.gap.com
Athleta Marlow Maxi Dress
$108
from athleta.gap.com
Buy Now

Old Navy Long-Sleeve Turtleneck Midi Sweater Shift Dress

Opting for colourful sneakers will really pop with either neutral grey Old Navy Long-Sleeve Turtleneck Midi Sweater Shift Dress ($40), or we like the soft pink dress paired with tan instead.

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Turtleneck Midi Sweater Shift Dress
$40
from oldnavy.gap.com
Buy Now

Lovers and Friends Langley Mini Dress

A peek-a-boo Lovers and Friends Langley Mini Dress ($148) added to sneakers turns this going-out-at-night dress into a chic option for a day date, too.

Image Source: revolve.com
Lovers and Friends Langley Mini Dress
$148
from revolve.com
Buy Now

Old Navy Sleeveless V-Neck Ribbed Maxi Shift Dress

The ultimate year-round layering piece, this Old Navy Sleeveless V-Neck Ribbed Maxi Shift Dress ($40) is never a bad choice with your favourite sneakers for a casual afternoon around town.

Image Source: oldnavy.gap.com
Old Navy Sleeveless V-Neck Ribbed Maxi Shift Dress
$40
from oldnavy.gap.com
Buy Now

Old Navy Puff-Sleeve Waist-Defined Smocked Mini Dress

The pretty patterns (or solid saffron) options of this Old Navy Puff-Sleeve Waist-Defined Smocked Mini Dress ($40) pop, but how cute are brightly colour socks down below, too?!

Image Source: oldnavy.gap.com
Old Navy Puff-Sleeve Waist-Defined Smocked Mini Dress
$40
from oldnavy.gap.com
Buy Now

Old Navy Waist-Defined Floral Tie-Belt Midi Wrap Dress

Get the perfect fit with this adjustable Old Navy Waist-Defined Floral Tie-Belt Midi Wrap Dress ($45) — and the perfect all-day walking 'fit with sneakers down below.

Image Source: oldnavy.gap.com
Old Navy Waist-Defined Floral Tie-Belt Midi Wrap Dress
$45
from oldnavy.gap.com
Buy Now

Free People Samantha Shirtdress

Wear a flowy Free People Samantha Shirtdress ($178) with well-worn sneakers for a casual everyday look (and opt for heeled sandals on a dressier day instead).

Image Source: nordstrom.com
Free People Samantha Shirtdress
$178
from nordstrom.com
Buy Now

Old Navy Long-Sleeve Fit and Flare Smocked Clip-Dot Midi Dress

Grab your favourite white sneaks and this Old Navy Long-Sleeve Fit and Flare Smocked Clip-Dot Midi Dress ($55) . . . and who needs a purse with those two roomy pockets?!

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Fit and Flare Smocked Clip-Dot Midi Dress
$55
from oldnavy.gap.com
Buy Now

Farm Rio Black Tropical Magic Mini Dress

A colourful option like this stunning Farm Rio Black Tropical Magic Mini Dress ($175) would prettily pair with equally bright sneakers or simple black mid-tops instead.

Image Source: farmrio.com
Farm Rio Black Tropical Magic Mini Dress
$175
from farmrio.com
Buy Now

Old Navy Long-Sleeve Fit and Flare Smocked Midi Dress

We'd match either floral Old Navy Long-Sleeve Fit and Flare Smocked Midi Dress ($55) with black high-top Chucks and a leather coat on chill, chilly days.

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Fit and Flare Smocked Midi Dress
$55
from oldnavy.gap.com
Buy Now

Sundry One Shoulder Dress

Grab white sneakers with a pop of colour and then slip a leather or denim jacket over this Sundry One Shoulder Dress ($158) for your next happy hour or evening out.

Image Source: revolve.com
Sundry One Shoulder Dress
$158
from revolve.com
Buy Now

Old Navy Long-Sleeve Poet Mini Swing Dress

Here's your new go-to outfit when Saturday plans also include brunch or lunch with friends: A baseball cap, sneakers, and any of the three colours of this breezy Old Navy Long-Sleeve Poet Mini Swing Dress ($40).

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Poet Mini Swing Dress
$40
from oldnavy.gap.com
Buy Now

Ted Baker London Long Sleeve Stretch Cotton Trench Minidress

Save 60 percent on the Ted Baker London Long Sleeve Stretch Cotton Trench Minidress ($158, originally $395) and wear it to work with leather sneakers instead of dress shoes this fall.

Image Source: nordstrom.com
Ted Baker London Long Sleeve Stretch Cotton Trench Minidress
$158
from nordstrom.com
Buy Now

BP. Babydoll Organic Cotton T-Shirt Dress

Babydoll dresses are definitely back, baby, and this BP. Babydoll Organic Cotton T-Shirt Dress ($35) is a soft pick to wear with sneakers now.

Image Source: nordstrom.com
BP. Babydoll Organic Cotton T-Shirt Dress
$35
from nordstrom.com
Buy Now

Old Navy Long-Sleeve Waist-Defined Ribbed Striped Midi Sweater Dress

It's hard to go wrong with an Old Navy Long-Sleeve Waist-Defined Ribbed Striped Midi Sweater Dress ($45) and bright white slip-on sneakers for autumn.

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Waist-Defined Ribbed Striped Midi Sweater Dress
$45
from oldnavy.gap.com
Buy Now

Old Navy Fit and Flare Rib-Knit Long-Sleeve Mini Dress

The loose Old Navy Fit and Flare Rib-Knit Long-Sleeve Mini Dress ($35-$40) is the type of outfit you can lounge around -- or work — in all day and still want to keep on with some sneakers when you head out to dinner, too.

Image Source: oldnavy.gap.com
Old Navy Fit and Flare Rib-Knit Long-Sleeve Mini Dress
$35
from oldnavy.gap.com
Buy Now

Old Navy Sleeveless Floral-Print Mini Swing Dress

Not only can this Old Navy Sleeveless Floral-Print Mini Swing Dress ($40) be your summer fave, it's a pretty pick on warm fall days (and there's no reason you can't put leggings or tights along with sneakers as well).

Image Source: oldnavy.gap.com
Old Navy Sleeveless Floral-Print Mini Swing Dress
$40
from oldnavy.gap.com
Buy Now

Old Navy Long-Sleeve Midi Sweatshirt Shift Dress

Instead of a matching sweatsuit and sneakers, why not pick this cosy Old Navy Long-Sleeve Midi Sweatshirt Shift Dress ($45) with your favourite neutral pair next?

Image Source: oldnavy.gap.com
Old Navy Long-Sleeve Midi Sweatshirt Shift Dress
$45
from oldnavy.gap.com
Buy Now

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