Though the summer heat is still blazing . . . I can already hear those pumpkin chai lattes calling my name. I’m so ready for fall everything — but mostly the cute and comfortable fashion. Since September is now officially creeping up, I’m shopping dresses that can take me from August heat into breezy, late October weather.
From breezy boho maxis to comfy tank dresses, I’m sharing my 17 favorite slimming dresses that transition easily from summer to fall. These picks will have your closet covered for both seasons, and they start at just $20.
17 Slimming Summer Dresses That’ll Carry You Straight Into Fall
Comfy, Errand-Running Picks
1. Our Favorite: I can’t imagine a transitional dress much better than this comfy maxi style . . . soft, versatile and has pockets!
2. Easily Layerable: From classic jean jackets to knit cardigan sweaters, this casual tank dress is easy to layer with your fall staples.
3. Has Pockets: There’s no better surprise than to realize your dress has pockets for carrying hands, keys and lipstick, which is why we love this flowy tiered style.
4. New and Notable: A newly added pick on Amazon, this tie-waist sundress is already a favorite of Amazon shoppers . . . thousands were bought in just the last month!
5. Boho Beauty: Perfect farmer’s markets and country concerts, this boho-style mini dress can be styled with both slides and booties.
17 Breezy, Boho Maxi Dresses That Transition Seamlessly to Fall
Brunch-Worthy Beauties
6. Our Favorite: Thanks to its lightweight fabric, this tiered midi dress is breathable enough for summer — but can also be layered in the fall too.
7. Boho Beauty: Nothing screams summer-to-fall transition quite like these breezy boho maxi that matches the vibes for both seasons.
8. Must-Have Maxi: Versatile and stylish, you’ll want to style this flowy maxi dress with both strappy sandals and knee-high boots.
9. Floral and Fabulous: The design of this wrap mini dress says summer . . . but its jewel-tone floral print channels fall.
10. Cutest Colors: This flattering floral mini dress comes in several color combinations that captures the fall aesthetic beautifully.
Polished Office Staples
11. Our Favorite: From rustic orange to faded olive, this chic shift dress has a color section made for both the warm and cool months.
12. One and Done: Make getting ready seamless from summer to fall with this two-in-one midi dress that’s high impact, low effort.
13. Pleated Perfection: With over 5,500 five-star ratings, shoppers agree: this pleated midi dress is totally worth the investment.
Wedding Guest Winners
14. Our Favorite: Get your fall wedding guest shopping done with this floral maxi dress that can be styled with a jacket should the weather turn cool.
15. Easy Elegance: Somehow, this floral tiered maxi can blend in for both summer and fall weddings . . . florals can just do that!
16. Boutique-Worthy: Love boutique-style fashion? Get it for less with this embroidered midi dress that brings the stylish vibes without the high price tag.
17. Pretty Polka Dots: No matter the season, polka dot dresses like this wrap midi style are always a good idea.
I’m 5’3″ — These 17 Petite-Friendly Maxi Dresses Are the Best I’ve Found on Amazon
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