The 20 Best Resort Wear Pieces for Your Next Island Vacation

best resort wear
The Best Resort Wear for Your Next Island Vacation


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One of the best parts of traveling somewhere warm during the thick of winter is easily the clothes. Going from the freezing cold to a deliciously sunny and balmy climate? There's truly no better than feeling than swapping a heavy puffer jacket and all your chunky knit sweaters for breezy caftans, the brightest of dresses, airy crochet pieces, and chic beach coverups. Johanna Ortiz, Zimmermann, Agua by Agua Bendita, and Farm Rio are just some of the many designers that excel at resort wear, but there are plenty of other labels that shine just as equally in the vacation-dressing department. To help with your shopping, we rounded up some of the season's best resort wear pieces for vacationing in style this winter, below.

Tyde Shirt Bayou Stripe Cobalt

SHOP MATCHING SHORTS

Stripes are a beach-side essential. And what's cool about this button down is that it comes with matching shorts that you can wear together over your favorite swimsuit. Then, later on, you can swap the bottoms for a pair of white jeans and wedges for dinner. It's the best of both worlds.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Ffaithfullthebrand.com%2Fproducts%2Ftyde-shirt-bayou-stripe-cobalt&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Tyde Shirt Bayou Stripe Cobalt</p><p>faithfullthebrand.com</p><p>$125.00</p>

Hunza G Jamie swimsuit Set

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.shopbop.com%2Fjamie-bikini-set-hunza-g%2Fvp%2Fv%3D1%2F1545043100.htm&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Hunza G Jamie swimsuit Set</p><p>shopbop.com</p><p>$245.00</p>

Flora Midi Dress

With a lightweight linen construction, a beaded halter neckline, and hot side slit, what you have here is the ultimate day-to-night vacation dress. Wear with strappy sandals during the day and then change into heels and chunky gold earrings for a dressier look. Your bound to look flawless either way.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.vixpaulahermanny.com%2Fcollections%2Fclothing%2Fproducts%2Fflora-midi-dress-ballet&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Flora Midi Dress</p><p>vixpaulahermanny.com</p><p>$269.00</p>

Vitamin A® Tallows Wide Leg Linen Cover-Up Pants in Ecolinen White at Nordstrom, Size Small

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.nordstrom.com%2Fs%2F7215234&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Vitamin A® Tallows Wide Leg Linen Cover-Up Pants in Ecolinen White at Nordstrom, Size Small</p><p>nordstrom.com</p><p>$125.00</p>

Devi Ruffled Crocheted Cotton Midi Dress

Crochet clothing is having a moment, and there's no better way to lean into the boho-inspired trend than with Zimmermann's knitted check dress with feminine ruffle tiers. Add in pair of mules and raffia evening bag to tie the look together, and you have the make up of a winning evening outfit.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Fzimmermann%2Fclothing%2Fmidi-dresses%2Fdevi-ruffled-crocheted-cotton-midi-dress%2F1647597316896857&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Devi Ruffled Crocheted Cotton Midi Dress</p><p>net-a-porter.com</p><p>$1150.00</p>

Plumeria Dress Ivory

Everyone needs that one breezy caftan that can go from beach day to apertivo with a few notable accessory changes. Savannah Morrow's relaxed caftan made of Turkish cotton and Turkish linen is exactly what we had in mind.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fsavannahmorrow.com%2Fproducts%2Fplumeria-dress-ivory&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Plumeria Dress Ivory</p><p>savannahmorrow.com</p><p>$500.00</p>

Sun Goddess Tie-Front Midi Dress

The tie-front cut-out center gives this Johanna Ortiz dress a slightly sultry touch, while the puffy-sleeves and midi silhouette ensures its still tasteful for dressier occasions.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.saksfifthavenue.com%2Fproduct%2Fjohanna-ortiz-sun-goddess-tie-front-midi-dress-0400018642980.html&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Sun Goddess Tie-Front Midi Dress</p><p>saksfifthavenue.com</p><p>$895.00</p>

+ NET SUSTAIN Lavanda Chivas floral-print cotton and silk-blend pareo

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Fagua-by-agua-bendita%2Fclothing%2Fcoverups%2Fplus-net-sustain-lavanda-chivas-floral-print-cotton-and-silk-blend-pareo%2F1647597303597940&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>+ NET SUSTAIN Lavanda Chivas floral-print cotton and silk-blend pareo</p><p>net-a-porter.com</p><p>$260.00</p>

Wexlee Long Sleeve Maxi Dress

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.lillypulitzer.com%2Fwexlee-long-sleeve-maxi-dress%2F014104.html&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Wexlee Long Sleeve Maxi Dress</p><p>lillypulitzer.com</p><p>$248.00</p>

Paola Kaftan

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.figue.com%2Fproducts%2Fpaola-kaftan&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Paola Kaftan</p><p>figue.com</p><p>$628.00</p>

+ NET SUSTAIN Spice Island crocheted midi skirt

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Fjohanna-ortiz%2Fclothing%2Fmidi%2Fplus-net-sustain-spice-island-crocheted-midi-skirt%2F1647597321757926&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>+ NET SUSTAIN Spice Island crocheted midi skirt</p><p>net-a-porter.com</p><p>$515.59</p>

Alight gathered printed linen midi dress

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Fzimmermann%2Fclothing%2Fmidi-dresses%2Falight-gathered-printed-linen-midi-dress%2F1647597326793219&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Alight gathered printed linen midi dress</p><p>net-a-porter.com</p><p>$850.00</p>

Oda strapless stretch-jersey maxi dress

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Feres%2Fclothing%2Fmidi-dresses%2Foda-strapless-stretch-jersey-maxi-dress%2F1647597320177201&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Oda strapless stretch-jersey maxi dress</p><p>net-a-porter.com</p><p>$465.00</p>

Irene scalloped broderie anglaise cotton-blend maxi dress

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.net-a-porter.com%2Fen-us%2Fshop%2Fproduct%2Fcharo-ruiz%2Fclothing%2Fmidi-dresses%2Firene-scalloped-broderie-anglaise-cotton-blend-maxi-dress%2F1647597309617652&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Irene scalloped broderie anglaise cotton-blend maxi dress</p><p>net-a-porter.com</p><p>$795.00</p>

Exclusive Summer Club Crocheted Silk Midi Dress

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.modaoperandi.com%2Fwomen%2Fp%2Falejandra-alonso-rojas%2Fexclusive-moda-summer-club-dress%2F579605&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Exclusive Summer Club Crocheted Silk Midi Dress</p><p>modaoperandi.com</p><p>$1995.00</p><span class="copyright">MODA OPERANDI</span>

Bunga Crocheted Cotton Pants and Top Set

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.modaoperandi.com%2Fwomen%2Fp%2Fakoia-swim%2Fbunga-pants-and-top%2F520992&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Bunga Crocheted Cotton Pants and Top Set</p><p>modaoperandi.com</p><p>$232.00</p>

lilac beaks & bananas v neck romper

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.farmrio.com%2Fproducts%2Flilac-beaks-bananas-v-neck-romper&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>lilac beaks & bananas v neck romper</p><p>farmrio.com</p><p>$200.00</p>

Melissa Odabash Martina Embroidered Lace-Up Linen & Cotton Cover-Up Dress in White/Hot Pink at Nordstrom, Size X-Small

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.nordstrom.com%2Fs%2F6616270&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Melissa Odabash Martina Embroidered Lace-Up Linen & Cotton Cover-Up Dress in White/Hot Pink at Nordstrom, Size X-Small</p><p>nordstrom.com</p><p>$258.00</p>

Barbara Dress Shell

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fciaolucia.com%2Fcollections%2Fresort-24%2Fproducts%2Fbarbara-dress-shell&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Barbara Dress Shell</p><p>ciaolucia.com</p><p>$335.00</p>

ZAYLA TOP - IVORY

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fpossethelabel.com%2Fcollections%2Fnew-arrivals%2Fproducts%2Fzayla-top&sref=https%3A%2F%2Fwww.townandcountrymag.com%2Fstyle%2Ffashion-trends%2Fg43966898%2Fbest-resort-wear-outfits-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>ZAYLA TOP - IVORY</p><p>possethelabel.com</p><p>$200.00</p>

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