40 Effortlessly Chic Outfit Ideas for Warm Winter Getaways

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STYLECASTER | Tropical Vacation Outfit Guide
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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.

MORE: The Top 20 Celebrities to Follow for Ultra-Glam Travel Inspiration

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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STYLECASTER | What to Wear for Your Winter Getaway 
Sunset Skirt
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STYLECASTER | What to Wear for Your Winter Getaway 
The Textured Dress

Dress, $1022 at Zeus + Dione

STYLECASTER | What to Wear for Your Winter Getaway 
Color Pop
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STYLECASTER | What to Wear for Your Winter Getaway 
Statement Earrings

Earrings, $58 at Baleen

STYLECASTER | What to Wear for Your Winter Getaway 
Hints of Floral
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STYLECASTER | What to Wear for Your Winter Getaway 
Greek Goddess Moment

Helena top, $185 at Ramy Brook

Diona skirt, $285 at Ramy Brook

STYLECASTER | What to Wear for Your Winter Getaway 
The Ultimate Travel Bag

Bag, $895 at Latitu

STYLECASTER | What to Wear for Your Winter Getaway 
The Orange Maxi
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STYLECASTER | What to Wear for Your Winter Getaway 
The Collapsible Clutch

Clutch, $378 at Cult Gaia

STYLECASTER | What to Wear for Your Winter Getaway 
The Vacation Tee
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STYLECASTER | What to Wear for Your Winter Getaway 
Floral Dress

Dress, $56.17 (was $74.90) at Torrid

STYLECASTER | What to Wear for Your Winter Getaway 
The Linen Dress

Dress, $750 at Amaió

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STYLECASTER | What to Wear for Your Winter Getaway 
The Tropical Jumpsuit
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STYLECASTER | What to Wear for Your Winter Getaway 
The Straw Clutch

Clutch, $94 at Hat Attack

STYLECASTER | What to Wear for Your Winter Getaway 
The Mini Cutout
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STYLECASTER | What to Wear for Your Winter Getaway 
One Shoulder Top

Top, $49.99 at Naked Zebra

STYLECASTER | What to Wear for Your Winter Getaway 
Toucan Tee
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STYLECASTER | What to Wear for Your Winter Getaway 
Bird of Paradise

Collar necklace, $88 at Accessory Concierge

STYLECASTER | What to Wear for Your Winter Getaway 
Vacation Night Out
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STYLECASTER | What to Wear for Your Winter Getaway 
The Clear Shades

Sunglasses, $92 at Poppy Lissiman

STYLECASTER | What to Wear for Your Winter Getaway 
Layered Bathing Suit
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STYLECASTER | What to Wear for Your Winter Getaway 
Travel Case

Case, $238 at Henri Bendel

STYLECASTER | What to Wear for Your Winter Getaway 
Lounge Pants

Pants, $160 at TWIG pants

STYLECASTER | What to Wear for Your Winter Getaway 
Dress Meets Denim
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STYLECASTER | What to Wear for Your Winter Getaway 
It's 5 O'Clock Somewhere

iPhone case, $29 at Casetify

STYLECASTER | What to Wear for Your Winter Getaway 
Beach Hat

The Ventura hat, $63 at Lack of Color

STYLECASTER | What to Wear for Your Winter Getaway 
The Printed Set
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STYLECASTER | What to Wear for Your Winter Getaway 
Little Red Dress

Backless dress, $70 at Tobi

STYLECASTER | What to Wear for Your Winter Getaway 
Classic Bikini

Suit, $67.20 (was $90) at Swimsuits For All

STYLECASTER | What to Wear for Your Winter Getaway 
Steal His Shirt
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STYLECASTER | What to Wear for Your Winter Getaway 
The Morning Star Choker

Choker, $55 at Jules Smith

STYLECASTER | What to Wear for Your Winter Getaway 
The Little Black Suit

One-piece, $169 at Lolli Swim

STYLECASTER | What to Wear for Your Winter Getaway 
The Jewel-toned Jumpsuit
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STYLECASTER | What to Wear for Your Winter Getaway 
The Bucket Bag

La Barra bag, $175 at Chila Bags

STYLECASTER | What to Wear for Your Winter Getaway 
The Chic Sneaker

Leather sneaker, $100 at TOMS

STYLECASTER | What to Wear for Your Winter Getaway 
Polka Dots
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STYLECASTER | What to Wear for Your Winter Getaway 
The Flutter Top

Top, $50 at Soluna

Bottoms, $48 at Soluna

STYLECASTER | What to Wear for Your Winter Getaway 
Dinner Dress

Dress, $228 at Rebecca Minkoff

STYLECASTER | What to Wear for Your Winter Getaway 
The Dotted Dress
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STYLECASTER | What to Wear for Your Winter Getaway 
Vintage Vibes

Top, $70 at Betsey Johnson

Bottoms, $56 at Betsey Johnson

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10 Pieces That Belong in Every Woman's Work Wardrobe

10 Pieces That Belong in Every
Woman's Work Wardrobe
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