Sneakers are the ultimate go-anywhere wardrobe staple. It’s pretty much a given that they’ll take you everywhere from a boxing class to the farmers market to the airport the next time you board a plane. But fashion girls are proving that they’re also a cool piece to wear with dresses, and everything from cute summer sundresses to structured styles make the cut. What are the pieces you should skip if you’re pairing your dress with sneakers?
We’ve noticed three things cool girls tend to steer clear of. First, avoid anything too tight. Instead of body-con styles, reach for looser fits. Second, skip super-short hemlines. Anything that’s knee length or even styles that hit the ankle are what we’ve been seeing all over the street style scene. And finally, leave your oversize bags at home. Stick to smaller styles that feel very of-the-moment.
Go on to see how fashion girls are wearing dresses with sneakers and then shop our favorite styles for your next look.
Shop cool dresses to wear with sneakers:
The cool-girl outfit for your office.Available in sizes 32 FR to 42 FR.
Nothing beats a classic wrap dress.Available in sizes 4 to 8.
Wear this style year-round.Available in sizes 10 to 18.
Did we just find this ultimate holiday dress?Available in sizes XS to XL.
The easy way to dress down an elegant dress? Add sneakers.Available in sizes 0 to 8.
Shop our favorite sneakers:
Try neutral sneakers on for size.Available in sizes 36 to 39.5.
These are destined for the street style scene.Available in sizes 5 to 11.
We love this cool mahogany rose shade.Available in sizes 6.5 to 10.
Clean and classic.Available in sizes 5 to 11.
You can't go wrong with this iconic style.Available in sizes 5 to 11.
These low-tops are super versatile.Available in sizes 34 IT to 42 IT.
A cult classic.Available in sizes 6 to 13.Next, read about the minimalist wardrobe staples you haven't tried yet.
-
Sure, Ballet Flats are Fine, But Women Over 50 Love This Controversial Flat Shoe Trend InsteadBye-bye, heels.
-
Every Time Bella Hadid Wears This Sneaker Trend, It Looks So Rich—I Found 13 Pairs Starting At $37Brown sneakers for the win.
-
Serious Fashion People Are Overlooking Designer Sneakers for This Rich Pair That's Only $36They're styling them with everything from jeans to wide-leg pants.
-
I've Given Up Chunky Sneakers, and Only Care About This Trendier Style (and My Favorites are On Sale for Black Friday)Chic. Period.
-
If You Want Your Sneakers to Look Elevated (Not Basic), Wear Them With These Pants Instead of JeansThis easy swap will work wonders to make your outfits look more sophisticated.
-
I'm a Shopping Editor—These Are the Cool Shoes I Care About From theReplica Store Black Friday SaleTake up to 60% off 2025 shoe trends inside.
-
Sneaker Haters (Myself Included) Loved This Cute Shoe Trend, and the $100 It Pair Is Finally Back in StockThe viral Adidas.
-
I'm Over Basic Sneakers—Here's My Editor-Approved Cool Adidas Wish ListShop up to 60% off Black Friday selects.
