Popsugar Fashion Fashion Shopping Best Dresses to Wear With Sneakers 2021 25 Dresses That’ll Complement Your Favourite Sneakers Better Than Pumpkin Spice Does Latte 20 October 2021 by Morgan Ashley Parker Image Source: Old Navy As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work. 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. Old Navy Waist-Defined Striped Tie-Belt Midi Wrap Dress Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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. Old Navy Ruffled Tie-Neck Chambray Swing Dress $45 from oldnavy.gap.com Buy Now Alo Yoga Cityscape Sweatshirt Dress Image Source: aloyoga.com 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. Alo Yoga Cityscape Sweatshirt Dress $118 from aloyoga.com Buy Now Old Navy Long-Sleeve Fit and Flare Slub-Knit Midi Dress Image Source: oldnavy.gap.com 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. Old Navy Long-Sleeve Fit and Flare Slub-Knit Midi Dress $40 from oldnavy.gap.com Buy Now Old Navy Smocked-Waist Fit and Flare Cami Midi Dress Image Source: oldnavy.gap.com 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. Old Navy Smocked-Waist Fit and Flare Cami Midi Dress $45 from oldnavy.gap.com Buy Now Superdown Ashanti Backless Dress Image Source: revolve.com 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. Superdown Ashanti Backless Dress $45 from revolve.com Buy Now Old Navy Long-Sleeve Floral-Print Poet Mini Swing Dress Image Source: oldnavy.gap.com 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. Old Navy Long-Sleeve Floral-Print Poet Mini Swing Dress $45 from oldnavy.gap.com Buy Now Athleta Marlow Maxi Dress Image Source: athleta.gap.com 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. Athleta Marlow Maxi Dress $108 from athleta.gap.com Buy Now Old Navy Long-Sleeve Turtleneck Midi Sweater Shift Dress Image Source: oldnavy.gap.com 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. Old Navy Long-Sleeve Turtleneck Midi Sweater Shift Dress $40 from oldnavy.gap.com Buy Now Lovers and Friends Langley Mini Dress Image Source: revolve.com 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. Lovers and Friends Langley Mini Dress $148 from revolve.com Buy Now Old Navy Sleeveless V-Neck Ribbed Maxi Shift Dress Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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?! 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 Image Source: oldnavy.gap.com 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. Old Navy Waist-Defined Floral Tie-Belt Midi Wrap Dress $45 from oldnavy.gap.com Buy Now Free People Samantha Shirtdress Image Source: nordstrom.com 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). Free People Samantha Shirtdress $178 from nordstrom.com Buy Now Old Navy Long-Sleeve Fit and Flare Smocked Clip-Dot Midi Dress Image Source: oldnavy.gap.com 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?! 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 Image Source: farmrio.com 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. Farm Rio Black Tropical Magic Mini Dress $175 from farmrio.com Buy Now Old Navy Long-Sleeve Fit and Flare Smocked Midi Dress Image Source: oldnavy.gap.com 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. Old Navy Long-Sleeve Fit and Flare Smocked Midi Dress $55 from oldnavy.gap.com Buy Now Sundry One Shoulder Dress Image Source: revolve.com 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. Sundry One Shoulder Dress $158 from revolve.com Buy Now Old Navy Long-Sleeve Poet Mini Swing Dress Image Source: oldnavy.gap.com 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). Old Navy Long-Sleeve Poet Mini Swing Dress $40 from oldnavy.gap.com Buy Now Ted Baker London Long Sleeve Stretch Cotton Trench Minidress Image Source: nordstrom.com 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. Ted Baker London Long Sleeve Stretch Cotton Trench Minidress $158 from nordstrom.com Buy Now BP. Babydoll Organic Cotton T-Shirt Dress Image Source: nordstrom.com 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. BP. Babydoll Organic Cotton T-Shirt Dress $35 from nordstrom.com Buy Now Old Navy Long-Sleeve Waist-Defined Ribbed Striped Midi Sweater Dress Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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. 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 Image Source: oldnavy.gap.com 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). Old Navy Sleeveless Floral-Print Mini Swing Dress $40 from oldnavy.gap.com Buy Now Old Navy Long-Sleeve Midi Sweatshirt Shift Dress Image Source: oldnavy.gap.com 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? Old Navy Long-Sleeve Midi Sweatshirt Shift Dress $45 from oldnavy.gap.com Buy Now ShoppingFashion ShoppingOld NavyFall FashionDresses