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Hamptons rich is a vibe — and no, you don’t actually need a trust fund or a summer house to pull it off. The secret? Effortless style that whispers “old money.” Nothing says quiet luxury quite like a loose, flowy button-down dress. Breezy, elegant and polished without trying too hard, it’s the kind of outfit you could wear straight from an iced matcha run to an art gallery opening. It’s your call whether to rock one barefoot on the beach or pair it with espadrilles.
We rounded up 16 button-down dresses that nail the look. Think crisp collars, relaxed silhouettes, coastal color palettes and timeless touches. From oversized shirtdresses you’ll want to live in to vacation-ready styles fit for sipping rosé, these picks are easy, elevated and seriously flattering — all while giving you that “just stepped off a yacht” energy. Read on to shop your new summer uniform.
16 Loose, Flowy Button-Down Dresses That Make You Look Hamptons-Rich
1. French-Inspired Favorite: This flowy dream of a dress feels like an effortless European summer outfit. The included tie belt makes it ultra-flattering and ultra-chic. . . yes, please!
2. Gingham Galore: A relaxed silhouette and summer-ready gingham print? Count Us in. This dress has big Hamptons energy — just add oversized sunnies and a straw tote.
3. Simple Maxi: Laid-back meets polished with this collared maxi dress. The best part? Pockets! Throw it on over a swimsuit as a cover-up, or add a belt for a stylish date night look.
4. Coastal Stripes: Shoppers adore Utcoco’s A-line maxi dress for every event on their calendar: Baby showers, Easter brunch and beach vacations. “The perfect coastal chic look — and a great look-for-less for trending coastal brands,” one shopper raved.
5. Flowy & Feminine: With tiered details and ruffled cap sleeves, this flowy maxi feels fresh out of a rom-com. Style it with strappy sandals and a low bun for that effortless Hamptons look.
6. Vacay-Casual Mini: Pack a lightweight mini design for your next trip. It’s flowy, lightweight and comes in several summer-ready prints. Bonus: It’s on sale right now for just $15.
7. Confidence Booster: Complete with a crisp collar, ruffled sleeves and a playful flowy hemline, this number has structure and softness. You’ll feel your best in a dress shoppers call “darling.”
8. Soft & Sweet: With flutter-y sleeves and button-front detailing, Wneedu’s breezy design is all about soft style. Pair it with chunky espadrilles and a woven bag for an instant style moment.
9. Lacy Babydoll: Cute, comfy and totally twirl-worthy! On hot days when you still want to look pulled together, opt for a fuss-free babydoll dress. It’s “a versatile dress that works for all occasions,” one shopper said.
10. Must-Have Denim: It’s rare that you come across a comfy, oversized denim dress that feels as good as it looks. The fabric is also breathable, so it’s a cute OOTD option even in the summer heat.
11. The ‘Perfect Summer Dress’: With its flowy skirt, soft fabric and pockets, this mini is a dream. “I can wear this casually with sneakers or dress it up a bit with a pair of platforms. The material is nice and airy. Will buy another color!” a shopper shared.
12. Linen-Look Luxe: This collared cutie is made with linen (and polyester for stretch), giving major resort energy. Reviewers note that the fabric doesn’t wrinkle, so it’s a great one to throw in your carry-on for your next getaway.
13. Boho Button-Down: With a swingy, breezy silhouette and adjustable spaghetti straps, this dress nails the boho-chic coastal look. Just add a beaded clutch and you’re golden.
14. Classic Shirt-Dress: This light cotton dress feels straight out of a Ralph Lauren summer spread. . . but really is under $45.
15. Timeless Maxi: Vrtige’s versatile design is crisp and classic. It’s a minimalist’s dream and pairs perfectly with gold accessories. Reviewers say it works for everything (the office, errands, etc.) and is even suitable for nursing moms thanks to the functional button-front.
16. Cheerful Cut-Out Dress: Made with soft fabric and an inner lining for comfort, this flowy midi is ideal for garden parties, weekend getaways and bottomless brunch. Meet your new favorite summer ‘fit!
