I’m Trading Coats for Caftans—Here’s My Winter Beach Packing List
From sunny dresses to playful matching sets, here’s a fun list of things to shop for your winter vacations.
Every year around this time, I hit a point where my brain can no longer process another coat. I’m starting to fantasize about warmer weather, ocean water, and the feeling of slipping into something breezy instead of bundling up into layers. So when I spent the first week of this month staying next to the ocean at The Shelbourne in Miami, I immediately started planning to spend every consecutive winter somewhere warmer, as one does. And thus beings, the packing list that can carry me through every beach vacation to come.
I’ve now edited that list down to the pieces I know I’ll actually wear—keeping in mind that there are colder days in beach towns during the winter that must be kept in mind. From easy linen pants for beach-to-dinner moments, playful sets that photograph beautifully, and the one-piece swimsuit I always feel confident in. If you’re headed somewhere warm, here’s everything I’m packing (and why each thing earned a spot in the suitcase).
Linen Pants
I think of this outfit as the ultimate winter vacation look. The linen pants can keep you comfortable at the peak heat of the day and the colder moments that follow. Plus, this halter top is something you’ll be able to wear again and again.
Long Sleeve Maxi Dresses
I tend to save long sleeve maxi dresses for the colder months in south Florida. A fun printed moment will never not be a vibe.
Playful Matching Sets
You can never have enough matching sets especially when visiting a warm weather destination. I love throwing something like this one anytime I’m in a rush or want to look put together, this one from Zimmermann is straight out of my dreams.
Bucket Hats
I’ve found one of the greatest upgrades to my vacation wardrobe have been hats that are easy to pack and go with everything. A bucket hat like this does it all and also if you have a poplin skirt in your repertoire you can’t go wrong.
Thong Sandals
Give me an ocean view and a luxe pair of thong sandals and I’m sold. I consider this minimal shoe trend to be non-negotiable when packing these days. They work with everything—linen pants, swimsuits, maxi dresses—and they instantly make outfits feel beachy without being too casual.
One Piece
The one-piece I always pack is the one I feel most confident in. A simple, sculpted suit is perfect for days when you want to swim, read, repeat without worrying about adjusting anything.

Sierra Mayhew is a fashion editor at Who What Wear, bringing a decade of industry experience to the editorial team. Since joining in 2021, she has made her mark by blending luxury and accessible fashion, decoding runway trends, and curating must-have shopping lists. Before joining Who What Wear, Sierra sharpened her skills at Harper's Bazaar and Elle, with bylines in Bazaar.com and collaborated with iconic brands such as Gucci and Ferragamo. A graduate of the University of Notre Dame, Sierra translates editorial expertise into viral social content, making fashion engaging for a new generation. Her unique perspective is rooted in her love for travel, music, and discovering the hidden gems that make New York City a constant source of inspiration.
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