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At its core, Hamptons style is about effortless chic, effortless silhouettes, rich seasonal tones, and just the right amount of understated luxury. The right clothes can get you there in no time. Hamptons-inspired fall dresses have the most floaty, flattering silhouettes that are perfect for a dinner party but effortless enough for a stroll through the farmers market.
From breezy maxis to laid-back midis, these Amazon finds impart true “quiet luxury” energy without the designer price tag. Whether paired with a cozy cardigan or layered with a suede jacket, these dresses capture all the luxe fall inspiration. Keep scrolling to find 21 roomy and flattering dresses that will keep you looking Hamptons chic all season long.
21 Roomy and Flattering Dresses for Fall Hamptons Style
1. Our favorite: Featuring a tan leaf print on a black background, this flowy midi dress feels like autumn leaves in style. Button embellishments add sparkle, while the loose fit creates a breezy feel.
2. Ruffle + preparation: This long-sleeve shift dress features a faux neckline and subtle ruffle trim for a “casual yet thoughtful” vibe. It looks perfect with boots for weekend brunch!
3. Cowboy Darling: Denim babydoll silhouette? Yes please. This flowy dress is the perfect example of the casual Hamptons look: comfortable, cute and versatile.
4. Start ready beauty: This two-tone dress (solid top, patterned skirt) is basically designed for ankle boots. Brown and white tones are full of autumn fashion.
5. Plum perfection: This square neck dress with balloon sleeves comes in deep purple, giving it a luxurious and dramatic feel…yet still comfortable and easy to wear!
6. Exquisite + playful: Gathered cuffs and a tiered skirt add a playful edge to this collared long top. It’s perfect for daytime wear but refreshing enough for a night out.
7. Put together preppy: This sweatshirt-and-skirt dress is comfortable and cool, making it a fall layering dream. It’s like your favorite jumper getting a chic Hamptons makeover.
8. Stripes + style: Stripes have always meant coastal fashion, and this gorgeous midi-length coat paired with a denim jacket is perfect for crisp fall days.
9. Chic half zipper: A half-zip, contrast details, and roomy pockets make this oversized sweatshirt dress perfect for running errands, grabbing coffee, or a casual dinner.
10. Coffee break: This long-sleeve tiered mini dress in a rich coffee brown hue (currently only $20!) is the perfect combination of comfort and sexiness.
11. Green Dream: This forest green belted dress flatters every figure and is available in over 15 shades. Pair with booties for an instant Hamptons feel.
12. Matching styling: This babydoll mini dress features a tie-front, puff sleeves, and lightweight pleating for a feminine yet effortless feel (perfect for a fall date night!).
13. Lace layer: Lace sleeves and a layered bodice add a romantic edge to this mini dress. This dress looks much more expensive than it actually is.
14. Food and wine: This one-shoulder gown features dramatic dolman sleeves and a rich burgundy hue, perfect for a wedding, date night, or fancy dinner.
15. Comfortable and chic: This wool-blend sweater dress is a dream to layer. Add leggings, knee-high boots, and a trench coat for a Hamptons vibe.
16. Swing style: This babydoll dress is flowy, flattering and sporty with tiered ties at the neckline.
17. Biggest Moment: A collared maxi dress with puff sleeves and pockets? Yes please. This shirt dress balances structured elegance with effortless flow.
18. Cable knit cool: Dropped shoulder comfort combines with a textured cable knit. Pair with boots for an effortlessly chic fall look.
19. High collar twist: This oversized turtleneck dress is basically a chic blanket that you can wear outside. You’ll love lounging in them for ultimate comfort or wear them for a chic, warm look.
20. Plaid and Polish: Pair this plaid one-piece dress with a cozy cardigan for a garden party chic feel, or pair it with a fitted turtleneck for a trendy, preppy feel.
21. Velvet Vision: This velvet maxi dress in a rich caramel hue instantly exudes elegance. The slim fit is perfect for everything from dinner parties to fall weddings.
