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Pairing boots with your favorite fall dress can be a moment, but nothing will ever compare to the comfort you feel while wearing sneakers. Sadly, not all dress styles go with kicks, which is why we went on a hunt for transitional options that’ll take you from August to November in style (and comfort).
Amazon is filled with summer-to-fall dresses that can pair nicely with your favorite kicks — whether they’re chunky or slim! If you’re looking to stock up on elevated work options, chic brunch styles or comfy everyday picks, we found a few dresses for every occasion. The best part? They all come in under $60, making it easy to give yourself a seasonal wardrobe update.
15 Summer-to-Fall Dresses That Pair Best With Sneakers
Easy Daytime Go-Tos
1. Our Favorite: Breezy and relaxed, this bestselling T-shirt-style maxi dress goes with Converse Chucks, Adidas Sambas and beyond. It’s no wonder the dress is an Amazon shopper-favorite.
2. Loose and Flowy: Step into cozy season with this loose and slimming dress that’s bound to feel as comfortable as your favorite loungewear.
3. Waist-Cinching: Thanks to its wrap silhouette, this slimming midi dress gives definition to the curves — all while remaining as comfy as your sneaks.
4. Throw-On-and-Go: The tiered midi dress is the perfect style to keep on hand for wearing around the house, running errands and for quick coffee dates. Can’t you just see them with plain white sneakers?
5. Darling Denim: The perfect fall pick, this denim babydoll dress can easily be styled with sleek lace-ups and a crossbody throughout the season.
6. Has Pockets: When you’ve got a pumpkin spiced latte in one hand and an apple cider donut in the other, you’ll want this striped mini dress with pockets, so you can go hands-free.
Brunch With Friends
7. Our Favorite: Though this embroidered maxi dress looks extra elegant, it can still be styled with a simple pair of white sneakers when the occasion calls for it.
8. One-Shoulder Wonder: Snag this one-shoulder floral dress in one of the many fall-inspired floral patterns. It’s available in rustic brown, deep evergreen and more.
9. Puff-Sleeve Perfection: No matter the season, you can’t go wrong with a puff-sleeve dress — especially a flowy, floral style like this!
10. Pretty Pastels: With an orange, yellow and green color palette, this stunning wrap dress perfectly emulates the changing of the leaves.
Polished Office Picks
11. Our Favorite: Easily go from work to weekend in this belted midi dress that makes it look like you put a full outfit together.
12. Everyday Staple: Wear this chic shift dress with sneakers for the commute and heels for a post-work dinner.
13. All-Day Comfort: Your boss will never know you’re taking meetings in loungewear . . . well, at least you’ll feel like you are in this soft and stretchy tiered midi dress.
14. Silhouette-Enhancing: Give your body some extra shape with this ruched-waist midi that’s just elevated enough for the office dress code.
Date-Night Dresses
15. Our Favorite: Perfect for a casual date night, this sheer wrap dress blends both romance and comfort.
16. Nicely Knitted: Thanks to its body-hugging design, this contrast knit dress shows off just the right amount of curve. Even though it looks super trendy, you can style it down with trainers for an everyday look, too.
17. Curve-Contouring: This bodycon midi dress fits the vibe for all sorts of date nights. Throw on your favorite sneakers for mini golf, dinner or a movie.
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