While Memorial Day weekend may be synonymous with the “unofficial” start of summer, it’s also the perfect time to dive into some of the season’s biggest trends. Teeny-tiny Matrix sunnies? Check. Vacay-ready sandals? Check. A brand-spankin’ new La Croix bathing suit and the ultimate color block visor to go with? Girllll, you know it. Ahead, we’ve compiled four foolproof #OOTDs that will be a match for all of your upcoming MDW plans, whether you’re making a splash at the first pool party of the season (strawberry rose cocktail in hand), jet-setting off to an exotic locale, or anything in between.

What to Wear for the Hamptons

A stint in the Hamptons or Montauk — your very own preppy paradise — will require a slew of resort-ready separates that transition from beach to bar, sunup to sundown. Snag the coveted Hamptonite look with this flowy Alice + Olivia palm leaf-inspired co-ord that’s ready to be ‘grammed alongside a watermelon margarita and sensible denim espadrille wedges that won’t sink into the sand. Be seen in a pair of these perennially chic tortoiseshell frames courtesy of Sunday Somewhere and some boho-fabulous gold tassel earrings. Last, but not least, allow Gelareh Mizrahi’s It girl-approved top-handle python clutch (Eek! Peep the palm tree charm) to serve as the talking point of your lewk. 

Clockwise from top left: Alice + Olivia Archer Cropped Cami ($165), Flaca Jewelry Sunrise Tassel Earrings ($150), Sunday Somewhere Kiteys ($270), Gelareh Mizrahi Top-Handle Python Clutch in Light Pink ($525), Privileged Aura ($45), Alice + Olivia Benny Smocked Wide Band Pant ($295)  

What to Wear for a Destination Wedding

Queue up the OOO (out-of-office) vibes — a destination wedding awaits you. The savvy jetsetter in you won’t be able to resist Paravel’s canvas and leather-trimmed Stowaway suitcase, featuring a collapsible structure and personalization options aplenty (ahem, hand-painted cactus emoji FTW). For an outdoor ceremony, stay cool in a breathable cotton shoulder-tie dress and a wide-brimmed straw sun hat. Proceed to slay on and off the dance floor with a pair of Kenneth Jay Lane’s beaded watermelon earrings and Loeffler Randall’s striped mules front and center. Protect your skin — and prevent your makeup from melting off — with a spritz of Coola’s SPF 30 water-resistant primer. C’est si facile!  

Clockwise from top left: & Other Stories Woven Straw Sun Hat ($45), Kenneth Jay Lane Beaded Watermelon Slice Drop Earrings ($110), Paravel Stowaway (starting at $325), Loeffler Randall Juno Kitten Heel Mule ($375), Iris & Ink Remy Gathered Cotton-Voile Dress ($155), Coola SPF 30 Makeup Primer ($42)

What to Wear for a Pool Party

For the 99 percent of you who decide to go glamping, BBQ-ing, or pool-side chilling, this festi-cool getup will fit the bill. Radiate good vibes with an itsy-bitsy, teenie-weenie yellow Sidway ‘kini. Follow suit with a trend-right net bag from Clare V. and a colorful striped Las Bayadas beach towel. If you’re living for the ’90s, then a pair of these comfortable neon star perforated sneakers will have you cruising around the boardwalk in style. And the fun doesn’t stop there: Toss on this rad customizable patch denim jacket from Beaus Babes for maximum #girlboss flair.

Clockwise from top left: Sidway Debbie Top in Daffodil ($90), Sidway Vivian Tie Side Bottom in Daffodil ($95), Beaus Babes Patch Jacket ($150), Las Bayadas La Teri ($69), Hollie Watman Starring 2 Tone Sneakers ($268), Clare V. Netty ($25)

What to Wear to the Vineyard

Gear up for rosé o’clock at the winery, be it Napa Valley or the North Fork, with an unstoppable lineup of style essentials. Crop it like it’s haute with this linen button-front top from Staud, some high-waisted vertical stripe shorts, and red pouf-topped thong sandals. Beat the heat index with a French Riviera-inspired Panama hat that will keep you company even in 90-degree temps. Stylish add-ons include Neely & Chloe’s best-selling ladylike buttercup yellow mini satchel and a stack of Roxanne Assoulin’s rainbow brite bracelets.

Clockwise from top left: Staud Cita Cropped Linen-Blend Top ($175), Hat Attack Panama Continental ($128), Neely & Chloe No. 19 The Mini Lady Bag Saffiano ($168), Roxanne Assoulin Rainbow Brite Bracelet (starting at $75), Frances Valentine Clementine Thong Feather Sandals in Red ($195), Alice + Olivia Scarlet High Waist Flutter Shorts ($265)

Which of these MDW-inspired getups will you be kicking off the unofficial start of summer in? Follow us on Pinterest for more styling inspo for the season!

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