Planning a trip to the Caribbean? With so many beautiful islands to visit, it's one of my favorite regions, but figuring out what to wear in the Caribbean can be as overwhelming as picking a destination.
This guide is full of Caribbean vacation outfit ideas--already put together for you from my recent trips--with essentials for your packing list and insider details I've learned from traveling across the islands. The looks in this article will have you feeling confident, comfortable, and ready to shine, sis!
And if you enjoy this post, you'll love my Mexico vacation outfits lookbook, too!
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Packing List for a Caribbean Vacation
Here's your Caribbean vacation packing checklist, with all the essentials I've personally used and refuse to travel without.
Swimsuits + Cover-ups--at least two so you always have a dry option!
Casual Daytime Outfits, like tank tops, tees, skirts, shorts, two-piece sets, dresses, and rompers. If you bring long pants, let it be these perfect linen trousers.
Dresses that are breathable, flowy, and easy to style from day to night. These options are linen, cotton, and silk.
Shoes that are comfortable, versatile, and easy to clean since you'll be in the sand. Think flat leather sandals, one pair of sneakers, and maybe a pair of wedges for a nice dinner.
Gear for Excursions, including activewear, a dry bag, hiking boots, a packable poncho, and water shoes (<--these are my tried-and-true for under $20!).
Accessories that are necessities: sun hat, sunglasses, statement earrings, and a small crossbody bag.
Beauty Products like sunscreen and lightweight makeup that won't melt in tropical temperatures. Read how to pack beauty products for airplane travel!
Despite being grouped together and sometimes confused for one another (Hello, Dominica vs. Dominican Republic!), no two island nations have exactly the same terrain or history, so you could be snorkeling off the coast of a black sand beach, swinging on a mountain top, or exploring underground crystal caves, depending on which one you visit.
Make sure you check out my island-specific packing lists for unique inclusions!
What should I not wear in the Caribbean?
Bulky Jeans - They're just too heavy for the heat. But cutoff shorts work.
Camouflage print or military-inspired clothing - Many Caribbean countries have outlawed this.
Stilletos - Even at the most exclusive luxury resorts, dress codes are more casual. I've packed high heels many times and rarely wore them!
Heavy Makeup - Opt for tinted moisturizer instead of full-coverage matte foundation, lip oil or sheer gloss over liquid lipstick, and a dewy highlighter vs. your typical contour routine.
Hot Hair Tools - It is very difficult to keep your hair straight in the humidity, so embrace your waves, curls, and coils, or do braids or twists. Or when all else fails, a good ol' slick back works.
Caribbean Climate Considerations
The Caribbean region stays warm year-round, but don't let that fool you. Humidity, sudden showers, and cooling trade winds can all play into what you'll want to pack. Rather than seasons of cold or hot weather, the two seasons are rainy (May through November) and dry (December through April).
Generally, you'll need lightweight attire--think short sleeves and breezy, natural fabrics like cotton and linen. No need for layers; just bring a cardigan or zip-up jacket to drape around your shoulders for air-conditioned restaurants and flights.
two-piece sets:
Check out my top things to do on vacation in San Juan!
Daytime Outfits
cute and casual with a little drama...
Visiting La Isla soon? Use my Puerto Rico women's packing list!
raffia sandals and mules:
Here are my favorite places to eat in the Cayman Islands!
vacation hats to complete the look:
Nightlife and Dinner Outfits
Elegant yet easy options to get dressy at night...
statement pants:
dresses with fringe:
Wondering whether to visit Dominica? Here's what to do on the Nature Island!
For resort cocktails in Grand Cayman: hot pink maxi dress | adjustable Chanel (worn as a belt bag) | French-hook hoops
The Cayman Islands are bougie, so your designer bags and pricier pieces will fit right in!
Caribbean vacation dresses:
Beach and Pool Outfits
styled swimwear and accessories...
statement swimsuits:
sexy sheer coverups:
beachy cover-up sets:
beautiful bikinis:
Read next: the best beaches in San Juan, PR!
Frequently Asked Questions
Yes, you need a couple of options for dinners and special events, especially if you're staying at a swanky all-inclusive resort. Even if you're solo traveling, dress to impress yourself!
I feel you--most of my Caribbean trips have been carry-on only! Read my guide on how to pack your carry-on bag and still have a stylish getaway.
Favorite Caribbean Destinations for Women
Now that you know what to pack for your Caribbean holiday, I'm wishing you the most enjoyable experience. And sharing is caring, so be sure to pin this post for later and follow me over on Pinterest. Thanks for reading!
Ask me a question!