From Montauk to Malibu: These 5 Vacation Looks Will Win You "Best Dressed"

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(Image credit: Original Illustration by Makena Frederick)

The coast is calling, and it's only right that I answer with booked flights and packed bags. But with so many destinations ahead of me, where do I even begin? No trip to a coastal town is complete without a pair of timeless Sperry shoes, and the brand's latest offerings are the reinvented classics I've been looking for. Every style from the Authentic Original™ Boat Shoe to the new SeaCycled™ Platform Sneaker is inspiring and elevating my vacation looks. There's nothing worse than looking back at photos and completely cringing at the outfits I put together, but these five are really hitting the mark if I do say so myself. So if you're headed to one of these destinations or looking for a dose of vacation outfit inspiration, keep scrolling to shop the looks I'm taking with me.


When packing for Montauk, go for elevated beach essentials. Swap denim shorts for a cotton pair, a baseball cap for a structured bucket hat, and a beach tote for a mini bag. But the number-one must-have for a trip to the East Coast beach town is a pair of Sperry boat shoes. I adore this navy-and-white combo for any coastal vacation, but they feel especially perfect for the Hamptons aesthetic.


When it comes to packing for a trip to Miami, you need pieces that will take you from the water to the beach club. We've got the bikini set, cover-up dress, a pop of color in the accessories, and the easiest slip-on Sperry sneaker. This outfit will have you feeling put-together even when you're coming straight from the sand.


To go from brunch to the boat on a Charleston vacation, this is the outfit to pack. A floral maxi dress, a sweater to throw over your shoulders, chic accessories, and the Sperry Authentic Original™ Boat Shoe are really all you need. This look encompasses that classic Southern charm while bringing in on-trend elements.


A trip to Malibu is all about relaxation, and your outfit should be just as laid-back. Opting for a one-piece swimsuit, staple denim shorts, and trusty beach hat is the way to go. Finishing off with a simple, baby-blue crossbody and platform Sperry shoes adds a bit of fun to a simple beach-day look. This is a no-fuss outfit that still maintains a level of trendiness.


Hawaii is the epicenter of corny tourist outfits, but this one is anything but. We've got a tasteful floral handbag, a modern-day shell necklace, and a pair of fun sunglasses that match the rich botanical color of the islands. Coordinating with this neutral Staud dress and Sperry boat shoes makes for the ultimate fashion-person take on vacationwear.

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Natalie Gray Herder
Editor, Branded Content

Natalie Gray Herder is an Editor on the branded content team at Who What Wear. Originally from Los Angeles, Natalie decided to make the move to NYC after graduating from Loyola Marymount University in 2019. She is an avid researcher, reader, and explorer in and out of the office. She is inspired by the street style of her fellow New Yorkers and her laid-back roots in California.