We spent the day in Sag Harbor with some of our favorite fashion girls to curate the ultimate guide to summer dressing. From white corsets to the perfect wedges, here is all the inspo you need for your next weekend away.
For New Yorkers, the Hamptons is a summer rite of passage. It’s the season where the ritual shifts from dodging subway heat to beach days, pool parties, and cocktails that are somehow even more overpriced than West Village. When Summer Fridays hit, if you don’t have a Jitney ticket or a house invite by 2 pm, you’re either braving the crowds at Coney Island or scrolling through your feed, sighing at friends who are tanning in Montauk.
As a West Coast born girl, I’ll admit that the Hamptons never held much allure for me. Sex and the City may have fueled my obsession with Manhattan, but it made the East End look like mediocre beaches filled with snobby parties and ex boyfriend sightings. However, a recent work trip to Sag Harbor officially changed my mind. Turns out, hiding from a New York heatwave is a lot more chic when there’s a salty breeze and a glass of orange wine involved.
We brought along some of our favorite girls for a day trip with Steve Madden, told them the dress code was "Hamptons Summer," and they delivered. We saw airy skirts, structured corsets, the continued return of the capri, and my personal favorite trend: heeled flip-flops. Whether you’re actually on the list for a celebrity Hamptons party or just hoping to look like you are, here is the ultimate outfit inspo, featuring the perfect summer shoe rotations.
Ava is a Creative Editor at OOTD. She graduated from the Fashion Institute of Technology and now covers your favorite fashion figures, events, and trends.
Nothing says "Out East" like a crisp, all-white palette. Brooke leaned into the monochrome look with baggy white linen shorts from Free People and a matching Par Foutch top. She finished the look with the Steve Madden Tracie J-brown sandal and the Tydes Natural Crochet Bag.
Similarly, Caroline looked like a summer dream in an off-the-shoulder white dress from Revolve, letting her accessories do the talking with Miu Miu sunnies, the Multi-Color Playing Wedge, and a matching Mishell Bag from Steve Madden.
Corinne made the Hamptons look like a romance novel. She elevated her sleek Steve Madden White Faroh Heels by pairing them with a white Guizio corset and a Mode Mischief skirt. The look felt perfect for catching the afternoon sun and gallery hopping, especially when finished off with a lace Urban Outfitters headscarf and a Chloe Paddington bag (the 2000s girlies know!)
Eden tapped into the "butter yellow" trend of the season. She paired a Zara skirt featuring a yellow trim with a 1950s vintage bra from Morephew. Layering a thrifted yellow button-up and her trusty Coach bag, she finished the look with Steve Madden Faroh Tortoise heels—the perfect outfit for getting wine-drunk with the girls at lunch.
The city-to-coast transition was best represented by the return of the capri. Kayla went playful in blue and white polka dots paired with a white lace top from Campbell, big sunnies from Versace, and the Brandy Raffia Platforms for some fun height.
Amanda gave us that Lower East Side edge with thrifted black capris, an H&M white tank, and a cheetah print bandana. Her Quay Sunglasses, Steve Madden Playing Tortoise Wedges, and Tydes Crochet Bag tied the city-girl and beach-chic look together perfectly.
If you need proof that a pair of flip-flops and a crochet bag are the ultimate duo, Jordan is the proof. In a sweeping long white dress from Zara, she used her Steve Madden Red Bella Sandals to provide a sharp, intentional pop of color. Between the thrifted bandana, Justine Clenquet jewelry, and the Voodoo Crochet Bag, she mastered the beach-to-shopping-to-cocktail-hour pivot perfectly.
After a day in Sag Harbor, my summer closet is currently screaming at me from under my bed (she’s tired of being teased by one 75-degree Tuesday followed by three days of rain). I’m officially trading my city layers for breezy skirts and Tracie Sandals. I left with a camera roll full of inspo and a shopping cart full of Steve Madden to get me through the rest of the season. See you guys out East!
