Hamptons style is all about looking effortlessly chic with relaxed silhouettes, rich seasonal hues and just the right touch of understated luxury. And the right dress can instantly transport you there. Hamptons-style fall dresses have the most flowy, flattering silhouettes that feel polished enough for a dinner party, yet easy enough for a stroll through the farmer’s market.
From breezy maxis to laid-back midis, these Amazon finds are giving serious “quiet luxury” energy without the designer price tags. Whether you layer them under a cozy cardigan or pair them with a suede jacket, these dresses capture all the luxurious fall inspo. Keep scrolling for 21 loose and flattering dresses that will have you serving Hamptons-chic all season long.
21 Loose and Flattering Dresses to Channel Hamptons Fall Style
1. Our Favorite: With its tan leaf print on a black backdrop, this flowy midi feels like fall foliage in fashion form. The button accents add polish, while the relaxed fit keeps it breezy.
2. Ruffle + Ready: Between the mock neckline and subtle ruffle trim, this long-sleeve shift has that “casual but curated” vibe. It looks so perfect paired with boots for weekend brunch!
3. Denim Darling: A denim babydoll silhouette? Yes, please. This flowy frock nails the Hamptons-off-duty look: comfy, cute and endlessly versatile.
4. Boot-Ready Beauty: This two-tone dress (solid top, patterned skirt) is basically made for ankle boots. The brown-and-white palette screams autumn chic.
5. Plum Perfection: In deep purple, this square-neck dress with lantern sleeves feels luxe and dramatic…but still comfortable and easy to throw on!
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6. Polished + Playful: The smocked sleeve cuffs and tiered skirt give this collared tunic a playful twist. It’s breezy enough for daytime wear, and polished enough for a night out.
7. Patchwork Preppy: Equal parts cozy and cool, this sweatshirt-meets-skirt dress is a fall layering dream. It’s like your favorite pullover got a chic Hamptons makeover.
8. Striped + Styled: Stripes always say coastal chic, and this gorgeous midi layers beautifully under a denim jacket for crisp fall days.
9. Half-Zip Chic: A half-zip, contrast details and roomy pockets make this oversized sweatshirt dress perfect for errands, coffee runs or casual dinners.
10. Coffee Break: In a rich coffee-brown shade (currently on sale for just $20!), this long-sleeve tiered mini is the perfect mix of cozy and flirty.
11. Green Dream: This forest-green tie-waist dress flatters every figure and comes in 15+ shades. Pair with booties for instant Hamptons polish.
12. Tie the Look: With a tie-front, puff sleeves and breezy pleats, this babydoll mini feels feminine yet fuss-free (ideal for fall date nights!).
13. Lace Layers: The lace sleeves and tiered bodice give this mini a romantic edge. It’s the kind of dress that looks way pricier than it is.
14. Wine & Dine: With its dramatic batwing sleeve and rich wine-red shade, this one-shoulder stunner is perfect for weddings, date nights or fancy dinners.
15. Cozy Chic: A wool-blend sweater dress that layers like a dream. Add tights, knee-high boots and a trench coat for peak Hamptons energy.
16. Swing Style: Tiered and tied at the neckline, this babydoll swing dress is flowy, flattering and full of movement.
17. Maxi Moment: A collared maxi with puff sleeves and pockets? Yes, please. This shirt dress balances structured polish with relaxed flow.
18. Cable Knit Cool: Drop-shoulder coziness meets a textured cable knit. Style with boots for an effortlessly chic fall ‘fit.
19. Turtleneck Twist: This oversized turtleneck dress is basically a chic blanket you can wear outside. You’ll love lounging in it for the ultimate coziness, or wear it out for a chic, warm look.
20. Plaid & Polished: This plaid overall dress feels garden-party chic with a cozy cardigan, or sleek and preppy layered over a fitted turtleneck.
21. Velvet Vision: In a rich caramel hue, this velvet maxi delivers instant elegance. It’s a flattering silhouette that works from dinner parties to fall weddings.
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