This post shows you the best Key West Outfits.
Heading to the vibrant paradise of Key West? Whether you’re sipping cocktails by the turquoise waters or exploring the colorful streets, you’ll want to look as fabulous as the island feels.
From breezy beach days to laid-back evening strolls, your outfits should be just as easygoing and fun as the island vibe. In this blog, we’ll share 15 outfit ideas to keep you stylish and comfy, no matter what your Key West adventure looks like.
So, pack your bags and get ready to rock these fun looks in this tropical haven!
What to Wear in Key West: 15 Key West Outfits
1. White Corset Sleeveless Short Dress and Black Slide Sandals
This look is giving tropical glam with zero effort. A white corset dress screams “vacation goddess,” while keeping things light and breezy in the Key West heat. Pair it with black slide sandals for an easy-breezy vibe that’s both cute and comfy. It’s perfect for brunch by the water or strolling through Old Town.
Don’t forget your sunnies and a straw bag to complete the effortlessly chic moment.
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2. Blue Gingham Tie Front Blouse, White Linen Beach Shorts, and Brown Flat Sandals
This outfit is picnic-perfect and totally Key West-approved. The blue gingham blouse adds a playful retro touch, especially with that flirty tie front.
White linen shorts keep it cool—literally—and make you feel like you’re on an endless summer vacay.
Brown flats are your BFF for all-day exploring without any fuss. It’s sweet, stylish, and screams let’s grab mojitos and wander!
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3. Green Stripe Crochet One Shoulder Top and Shorts Set with Brown Flat Sandals
Who said crochet was just for grandma? This green one-shoulder crochet set is giving island vibes in the best way.
It’s bold, breathable, and looks like you planned your outfit way more than you did. The matching shorts and top make it a no-brainer, while brown flats keep it grounded (and ready for beach bars).
Get ready for compliments from strangers—this one’s a head-turner.
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4. White Twist Knot Tank Top, Printed Detail Wide Leg Pants, and Green Flat Sandals
This outfit has vacation written all over it—laidback but polished.
The twist knot tank adds a flirty touch, while those printed wide-leg pants do all the talking. It’s one of those combos that works for both daytime market strolls and sunset cocktails.
Green sandals give it a little pop and tie it all together. Add a beachy wave to your hair and you’re basically a walking Key West postcard.
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5. Floral Crop Top and Skirt Set with White Strappy Heels
Florals? In the tropics? Groundbreaking—and also gorgeous.
This matching crop top and skirt set is flirty and fabulous for dinner dates or dancing under the stars. The white strappy heels add just enough elegance without being over-the-top.
Throw on some gold hoops and you’re instantly island glam.
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6. Geometric Printed Long Summer Dress and Black Strappy Heels
This dress is giving “I woke up fabulous and just happened to be in paradise.”
The geometric print brings some artsy edge to your vacay look, while the flowy fabric keeps things cool and comfy. Black strappy heels dress it up just enough for fancy dinners or rooftop cocktails. It’s that kind of effortlessly stunning look that makes you feel like the main character.
Bonus: it twirls so well for those golden hour photo ops.
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7. White Ribbed Tank Top, Green Floral Mini Skirt, and Flat Sandals
Simple, sweet, and oh-so Key West. The white ribbed tank is a closet MVP that pairs perfectly with a flirty green floral mini skirt.
Add comfy flat sandals and you’ve got the ideal outfit for everything from beach walks to taco runs. It’s laidback, cute, and totally Instagram-worthy.
Toss on a floppy hat and you’ve nailed the tropical casual vibe.
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8. White Ribbed Crop Top, Wide Leg Linen Pants, and White Flats
This look says “effortlessly cool” louder than a seagull stealing your French fries.
A white ribbed crop top is a sunny-day staple, especially when paired with wide leg linen pants that feel like a breeze in motion. The all-white combo is super clean and super chic.
White flats keep it relaxed, whether you’re hitting up a local art gallery or sipping iced coffee on Duval Street. Add some layered necklaces and a woven tote for extra flair.
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9. Green Floral Tie Backless Dress and White Heels
Flirty, floral, and just a little bit spicy.
This green tie-back dress is made for twirling at sunset and stealing hearts. The backless detail adds a dash of drama while still keeping it vacation-friendly.
Pair it with white heels for a dressy finish that’s still beach-town appropriate. It’s the kind of outfit that makes you feel like you’re starring in a romantic summer movie.
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10. White Button Down Shirt, Cream Satin Skirt, and Black Flat Sandals
Classy with a tropical twist—yes, please! A crisp white button down tucked into a dreamy satin skirt is all kinds of elegant.
It’s perfect for a fancy dinner or gallery night without feeling stuffy. The black sandals ground the look and make it easy to wander through those charming little Key West streets. Add a bold lip and a clutch for instant vacation glam.
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11. White Button Down Shirt, White Linen Shorts, and Ballet Flats
This outfit is basically your coastal chic starter pack.
A breezy white button down and white linen shorts are a match made in sunshine heaven. It’s clean, crisp, and totally brunch-ready.
Ballet flats add a sweet touch that’s both comfy and cute. Toss your hair in a bun, grab your iced latte, and you’re good to go.
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12. White Lace Strap Tank Top, White Boho Maxi Skirt, and Beige Mules
Boho girls, this one’s for you. The lace strap tank and flowing maxi skirt combo is romantic, beachy, and gives off barefoot-in-the-sand energy—even if you’re actually in cute beige mules.
It’s floaty, feminine, and perfect for sunset photoshoots or candlelit seafood dinners. Throw on a shell necklace and a flower in your hair for full tropical goddess mode.
It’s dreamy, it’s effortless, and it’s so Key West.
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13. Pink Floral Maxi Dress and Black Flip Flops
This is the “I just threw this on and still look amazing” outfit.
A pink floral maxi dress keeps things light and pretty, with just the right amount of flair. Pair it with black flip flops for a totally relaxed, beach-town look that still feels intentional.
It’s ideal for browsing local shops or grabbing a popsicle on a hot day. Add a straw hat and you’re the picture of tropical ease.
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14. White One Shoulder Ribbed Top, Black Maxi Skirt, and White Sneakers
Chic and sporty all in one cute outfit. The white one-shoulder ribbed top gives it a trendy edge, while the black maxi skirt adds flow and movement.
White sneakers keep it comfortable enough to explore all day, without sacrificing style. It’s perfect for wandering museums, snapping pics, and ending the day with fish tacos and live music.
Easy, cool, and totally Key West street-style ready.
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15. White Ruffle Chiffon Blouse and Denim Shorts
This look is flirty, fun, and a little bit beachy. The ruffle chiffon blouse brings a soft, romantic touch, and pairs perfectly with classic denim shorts.
Whether you’re hopping between shops or sipping on a rum punch, you’ll look effortlessly cute. Add espadrilles or simple sandals and you’re ready for anything the island throws at you.
It’s that perfect balance of pretty and practical.
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