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Fall is almost here, and it’s the perfect time to grab comfy, transitional weather dresses to wear as soon as pumpkin spice season arrives. It’s also time to master the art of pairing flowy frocks with chic boots — whether you’re slipping into ankle booties for a casual day out or knee-high stunners for a night on the town.
To help you nail the seasonal switch-up, we rounded up 17 summer-to-fall dresses on Amazon that were practically made to pair with boots. The best part? Each piece can carry you seamlessly from late summer afternoons to crisp fall evenings, all while keeping your wardrobe feeling fresh.
17 Summer-to-Fall Dresses That Pair Well With Boots
1. Our Favorite: Looking for maximum impact with minimal effort? This tiered maxi delivers. The puff sleeves balance the floaty skirt, and we love how versatile it is — ankle boots for daytime, heeled boots for date night.
2. Floral & Feminine: This sweet floral pick features a square neckline and breezy 3/4 sleeves. It’s giving countryside picnic, but paired with boots and a denim jacket, it’s instantly autumn chic.
3. Plum Perfection: The deep purple shade on this lantern-sleeve dress feels regal yet wearable. The square neckline and A-line silhouette are universally flattering, while the flowy fabric pairs beautifully with tall boots for an instant fall-ready look.
4. Eyelet Obsession: Romantic eyelet embroidery never goes out of style. This sweet mini dress has a lightweight feel that works now with sandals, but will look just as dreamy layered under a leather jacket with booties come fall.
5. Mixed & Matched: This dress does the styling work for you with its solid top and patterned skirt combo. The warm brown-and-white palette screams fall, and it looks especially polished with suede ankle boots.
6. Curve Appeal: Reviewers rave that this swingy dress “fits like a glove” without being clingy — the ideal mix of flirty and flattering. Pair with knee-high boots and you’ll be turning heads at every fall gathering.
7. Cozy Babydoll: Nothing says fall layering quite like a sweater dress. This babydoll version feels playful yet polished, and it looks amazing with ankle boots — especially if they have a little block heel.
8. Cocoa Crush: Rich brown tones are trending big for fall, and this ribbed knit dress is an easy way to work the look. The long sleeves and soft fabric make it as comfy as it is chic.
9. Striped & Sophisticated: This maxi brings the drama with its mockneck top and contrasting striped skirt. Tie the waist to cinch your figure, then finish with tall boots for a runway-ready ensemble.
10. Effortless Tie-Up: A cinched waist always flatters, and this knit mini makes it effortless. The cozy fabric works for the office or brunch, and ankle booties are the perfect finishing touch.
11. Denim Days: A denim dress never disappoints. This long-sleeve babydoll version is casual-cool with sneakers, but swap in boots and a wide belt and you’ve got a fall staple.
12. Sporty Chic: The sweatshirt-inspired vibe of this striped dress makes it a weekend go-to. It’s playful, comfy and looks great with white sneakers or chunky ankle boots.
13. Shift into Style: With its breezy shift shape and mock-neck ruffle detail, this dress proves that simple doesn’t have to be boring. Add over-the-knee boots and you’re golden.
14. Buttoned Beauty: The button accents on this short-sleeve dress give it a little vintage flair. It’s breezy enough for late summer but transitions seamlessly with a cardigan and boots.
15. Moody Midi: Long puff sleeves and a tiered skirt give this midi major movement. Style with heeled boots and statement earrings for an easy day-to-night outfit.
16. Dot Darling: Swiss dot fabric always feels extra feminine, and this mini dress is no exception. Pair it with ankle boots now, then layer it with tights and tall boots once the temps drop.
17. Cutout Chic: With its hollow-out lace and v-neck cutout, this mini is all about the details. It’s flirty, fun and an instant match with block-heeled booties.
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