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 [1], 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 [2] like including minis (and high-tops), midis (plus slip-ons), and maxis (with classic canvas). Whether your shoe preference is white [3], 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.
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 [4] ($45) would be oh-so-pretty with a classic pair of canvas sneakers.
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 [5] ($45) look is no exception.
Alo Yoga Cityscape Sweatshirt Dress
While the belt on the Alo Yoga Cityscape Sweatshirt Dress [6] ($118) can be removed, it's an extra sporty accessory to your favourite running shoes while running all around town.
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 [7] ($40) and slip-on sneakers equal one solid choice to trek through apple orchards this season.
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 [8] ($45) looks with comfy sneakers as well.
Superdown Ashanti Backless Dress
We especially like this fitted Superdown Ashanti Backless Dress [9] ($45, originally $64) with a chunky dad sneaker or pair of Air Force 1s [10] for fall.
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 [11] ($45) ASAP.
Athleta Marlow Maxi Dress
The Athleta Marlow Maxi Dress [12] ($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.
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 [13] ($40), or we like the soft pink dress paired with tan instead.
Lovers and Friends Langley Mini Dress
A peek-a-boo Lovers and Friends Langley Mini Dress [14] ($148) added to sneakers turns this going-out-at-night dress into a chic option for a day date, too.
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 [15] ($40) is never a bad choice with your favourite sneakers for a casual afternoon around town.
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 [16] ($40) pop, but how cute are brightly colour socks down below, too?!
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 [17] ($45) — and the perfect all-day walking 'fit with sneakers down below.
Free People Samantha Shirtdress
Wear a flowy Free People Samantha Shirtdress [18] ($178) with well-worn sneakers for a casual everyday look (and opt for heeled sandals on a dressier day instead).
Old Navy Long-Sleeve Fit and Flare Smocked Clip-Dot Midi Dress
Grab your favourite white sneaks [19] and this Old Navy Long-Sleeve Fit and Flare Smocked Clip-Dot Midi Dress [20] ($55) . . . and who needs a purse with those two roomy pockets?!
Farm Rio Black Tropical Magic Mini Dress
A colourful option like this stunning Farm Rio Black Tropical Magic Mini Dress [21] ($175) would prettily pair with equally bright sneakers or simple black mid-tops instead.
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 [22] ($55) with black high-top Chucks and a leather coat on chill, chilly days.
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 [23] ($158) for your next happy hour or evening out.
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 [24] ($40).
Ted Baker London Long Sleeve Stretch Cotton Trench Minidress
Save 60 percent on the Ted Baker London Long Sleeve Stretch Cotton Trench Minidress [25] ($158, originally $395) and wear it to work with leather sneakers instead of dress shoes this fall.
BP. Babydoll Organic Cotton T-Shirt Dress
Babydoll dresses are definitely back, baby, and this BP. Babydoll Organic Cotton T-Shirt Dress [26] ($35) is a soft pick to wear with sneakers 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 [27] ($45) and bright white slip-on sneakers for autumn.
Old Navy Fit and Flare Rib-Knit Long-Sleeve Mini Dress
The loose Old Navy Fit and Flare Rib-Knit Long-Sleeve Mini Dress [28] ($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.
Old Navy Sleeveless Floral-Print Mini Swing Dress
Not only can this Old Navy Sleeveless Floral-Print Mini Swing Dress [29] ($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).
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 [30] ($45) with your favourite neutral pair next?