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40 Effortlessly Chic Outfit Ideas for Warm Winter Getaways

The best resort wear, cover-ups, hats, and more.
STYLECASTER | Winter Vacation Outfit Guide

In spite of (and probably because of) the freezing temperatures outside, we’re currently daydreaming nonstop about grabbing our passports, packing our weekenders and jet-setting away from New York, to somewhere warm, where happy hour never ends. Whether you’re actually headed to a tropical destination—lucky!—or are just seeking some style inspo that doesn’t involve scarves, wool, and 75 layers, you’ve come to the right place.

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We combed through the interwebs to find you the best resort wear, must-have accessories and killer outfit inspiration. We’re into eye-catching maxi dresses that you can wear over your swimsuit or out to dinner, graphic jewelry to instantly elevate any look, and of course chic clutches to carry all your necessities in style—because a laptop-ready tote or work handbag has no place on vacation.

MORE: 55 Winter Travel Outfits That Look A-Plus Upon Arrival

The key to dressing and packing smart for any trip is to find items you can transition into multiple outfits. Wear your bikini top as a regular top, or pair your cover-up with jeans for a cool dress-meets-denim combo. The options are endless, and let’s be real, February is never too early to start outfit planning your next vacation—even if it’s not until May.

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