The 20 Best Resort Wear Pieces 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.

Lilac Breaks & Bananas V Neck Romper

Rule No. 1 of resort wear: Always go for statement-making colors and patterns. No one does a combination of the two better than Farm Rio. Case in point: this colorful, tropical-inspired romper that's perfect for daytime adventures as it is for ocean-side dinners.

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.

Jamie swimsuit Set

Hunza G has long been a cult-favorite among celebrities and the fashion set, and for good reason. The swimwear is made of seersucker, which is more lightweight than linen, and is sold as one-size that molds and flatters most body types.

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.

Tallows Wide Leg Linen Cover-Up Pants

Linen is always a "do" in warmer climates. Try these carefree linen pants with your go-to swimsuit, a straw hat, and oversized sunglasses for a laidback vacay look.

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.

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.

Bunga Crocheted Cotton Pants and Top Set

Crochet clothing was huge over the summer, and it's not going away anytime soon. Our favorite way to wear it? As a matching two piece, of course. Wear over your favorite swimsuit to the beach or solo for island excursions.

Devi Ruffled Crocheted Cotton Midi Dress

Or, you can lean into the boho-inspired trend with Zimmermann's knitted check dress with feminine ruffle tiers. Add in pair of mules and raffia evening bag, and you have the make up of a winning evening outfit.

Wexlee Long Sleeve Maxi Dress

Lilly Pulitzer knows a thing or two about fun and timeless resort wear. Just imagine how fabulous this tropical maxi will look with wedges for a sunset aperitivo on the beach! I rest my case.

Lavanda Chivas Floral-Print Cotton and Silk-Blend Pareo

This floral pareo looks great wrapped around any swimsuit, but we'd argue it looks even better paired with the matching one piece.

Paola Kaftan

A timeless black caftan featuring white embroidery will be in constant rotation long after you return from your getaway. You can wear it with sandals, heels, sneakers—it'll look chic no matter which way you style it.

Spice Island Crocheted Midi Skirt

SHOP MATCHING TOP

Johanna Ortiz masters vacation-wear again with crocheted patchwork halter top and matching maxi skirt. Proof of what's old is new again.

Martina Embroidered Lace-Up Linen & Cotton Cover-Up Dress

Melissa Odabash's simple and delicate coverup will work perfectly over just about any swimsuit or maillot.

Alight Gathered Printed Linen Midi Dress

Made of breezy linen and featuring a print of flowers, beaches, and maps, this Zimmermann dress was truly made for a holiday in paradise.

Oda strapless stretch-jersey maxi dress

If you're only taking a carry-on with you—and let's face it, you should!—this simple strapless black maxi dress is just the piece to pack. With a few notable accessory changes, this easy number will most certainly become the workhorse of your suitcase.

Irene Scalloped Broderie Anglaise Cotton-Blend Maxi Dress

Eyelet will always be a warm weather classic, especially if it comes in dress as cute as this one.

Exclusive Summer Club Crocheted Silk Midi Dress

If it's a bold look you're after, Alejandra Alonso Rojas has you covered with an anything-but-boring crochet dress that will surely turn heads.

Barbara Dress Shell

Looking for the perfect vacation dress? Might we suggest Ciao Lucia's sea shell-printed frock featuring a flattering smocked bodice? Cute as can be.

Zayla Top

SHOP MATCHING SKIRT

Whether you wear this scallop-trimmed top as a separate with jeans or as a co-ord with the matching skirt, it's bound to become your most worn piece of your warm-weather wardrobe.

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