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15 Vacation-Ready Dresses Perfect For the Pool or Cocktail Hour

Dresses that look great, from Palm Beach to Palm Springs.
by In The Groove February 4, 2025
15 Vacation-Ready Dresses Perfect For the Pool or Cocktail Hour

If you’re one of the lucky few who have fled winter for warmer climates, for pickleball, for long walks in sunshine: this email is for you. We put together an edit of pretty dresses that will work from Palm Beach to Palm Springs. And if you’re still in winter, well, you need something to look forward to, don’t you? 

One of my favorite brands for hard-working dresses is Tuckernuck. Maybe it’s their Southern DNA, but they always nail the balance of comfortable and cute, without showing too much skin. The lilac lace dress I’m wearing in the header image is a perfect example. The pretty lace pattern shows shows just enough to keep the dress from feeling too conservative. I’m also very into this tan crochet dress, with cream cuffs, collar, and hem. It’s just the amount of contrast. And for a more literal caftan-y option, this white and tan embroidered caftan is begging to be worn on a breezy day by the pool.

All three of those dresses have a very specific retro, nostalgic look. Like you could be in the background of one of Slim Aaron’s iconic poolside shots. But that’s not the only look out there. Maybe you want something a little more feminine or boho? How about a pretty pink block printed caftan? Doen has so many great floral dresses, like this dainty blue-and-yellow wildflower dress with cap sleeves.

A lot of the resort options are colorful and printed, like this gorgeous rainbow striped dress from Tuckernuck. But there are plenty of beautiful more neutral options for the minimalists out there. Farm Rio, a Brazilian brand perfect for lounging, has a beautiful beige cover up with a tonal palm tree motif. Or you can go with a tan, spaghetti strap maxi dress that you can dress up with fun jewelry.

Shop our favorite resort dresses below:

All of our recommendations are curated by Susan & the In The Groove editorial team. In some, but not all cases, we receive a small commission for leading you to what, how, and where to buy all this wonderful stuff.

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