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

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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