Checking Into a Luxury Caribbean Resort? Here’s What to Pack

• Eleven designer picks cover what to wear at a luxury Caribbean resort, from ERES swimwear and linen separates to Johanna Ortiz dresses and a Saint Laurent raffia tote.

• Lightweight fabrics, versatile outfits, and comfortable flat sandals form the foundation of a wardrobe for pool days, afternoons in town, and dinner reservations.

• Restaurant dress codes vary, even within the same resort. Check requirements before packing, particularly for men’s trousers and closed shoes.

• For seven nights, start with three swimwear options, a small rotation of daytime clothes, and three dinner outfits you can repeat, adding pieces for planned excursions.

Packing for the Caribbean usually starts with swimwear. It gets more complicated when you think about everything you will do between swims. There is lunch at the hotel, perhaps an afternoon in town, and dinner somewhere with a beautiful view. You want to feel well dressed for all of it, preferably without taking a second suitcase.

A few good pieces can cover much of the trip. A swimsuit you feel comfortable spending the morning in, a cover-up you can wear to lunch, and sandals that will get you farther than the pool are useful places to start. A dress you are excited to wear deserves room, too. The same goes for a good linen shirt or a pair of properly tailored swim shorts. Practical clothes can still be a pleasure to put on.

How much else you need depends on where you are staying and what you have planned. A week spent mostly on the beach in Anguilla calls for a different suitcase from a St. Barts itinerary with dinner reservations every night. Before buying anything, look at your resort’s restaurant dress codes and give some thought to how often you will leave the property.

This luxury resort packing list brings together swimwear, dresses, shirts, sandals and accessories for a Caribbean wardrobe you will actually use, with enough variety to enjoy getting dressed and enough overlap to wear your favorites again.

Johanna Ortiz Saffron Breeze Silk Maxi Dress

This is the dress I would pack for a dinner reservation at a nice restaurant. The peach-and-ecru print, wrap waist, and softly pleated silk georgette give it plenty of detail without needing much jewelry. Wear it with simple sandals and a small evening bag.

Camilla Pottery Parlour Linen Tie-Front Maxi Dress

Linen is a welcome choice when dinner is outdoors and the evening is still warm. This Camilla maxi is made from 100% linen, with adjustable straps, a V-neckline, and a knotted tie at the bust. The Pottery Parlour print gives it enough interest to keep accessories simple. We would wear it with gold earrings and flat dress sandals, then bring it out again for a long lunch later in the week.

Polo Ralph Lauren Linen Short-Sleeve Midi Shirtdress

A white shirtdress makes getting dressed for breakfast easy, even if you have plans to stay out until dinner. This Polo Ralph Lauren version is made from 100% linen, with short sleeves, a notched collar, and a button front. A shaped waist gives way to a full A-line skirt, giving it enough structure to feel dressed without needing many accessories. We would wear it with the woven leather sandals and raffia tote for lunch and an afternoon exploring town.

ERES Asia One-Piece Swimsuit

With broad straps and a scoop neckline, ERES’s Asia one-piece looks much like a fitted tank when worn with trousers or a skirt. The waist panel adds definition, while the white shade makes it easy to pair with anything. Once it is dry, we would add linen trousers, woven leather sandals, and a raffia bag for lunch.

SIMKHAI Jensen Macramé Midi Dress

SIMKHAI’s Jensen gives a simple swimsuit a little more interest with open macramé and a fringed hem. The sleeveless midi dress pulls on overhead, making it easy to add before heading to the beach bar. We would wear it over a cream one-piece with flat sandals and a generous tote.

LoveShackFancy Delano Eyelet Linen Button-Front Shirt

A linen shirt is useful on the days when you leave the hotel without knowing exactly when you will be back. LoveShackFancy’s Delano has a relaxed fit, long sleeves, and floral eyelet trim, with a scalloped hem worth leaving untucked. We would wear it with high-waisted shorts for an afternoon in town.

TWP Cornelia St Linen Pleated Pants

These are the trousers we would pack for days when lunch turns into an afternoon out. Made in the USA from 100% linen, TWP’s Cornelia St pants combine front pleats with a relaxed fit and a tapered leg. In Ivoire, they would pair easily with the black Prada one-piece once dry, or the LoveShackFancy shirt and woven leather flats. For dinner, add a simple camisole and your evening sandals.

BVLGARI Serpenti 63MM Butterfly Sunglasses

Sunglasses may be the accessory you wear most on a Caribbean trip, so choose a pair you enjoy putting on. BVLGARI’s Italian-made Serpenti butterfly frames combine rose gold metal with grey gradient lenses, adding a little glamour to a simple linen shirt and shorts. The lenses offer UV protection, while adjustable nose pads let you fine-tune the fit.

Aquazzura Ce Soir Leather Stiletto Sandals

If you enjoy dressing for dinner, one pair of evening heels can earn its place in the suitcase. We would pack Aquazzura’s Ce Soir sandals to wear with a linen dress or wide-leg trousers and a simple top, keeping the rest of the outfit understated. Save them for evenings with a short walk to the restaurant and a firm surface underfoot. For dinner on the sand, your flat sandals will be a better choice.

Gianvito Rossi Woven Leather Flat Sandals

A good pair of flats should work with most of your suitcase. These Italian-made Gianvito Rossi sandals have woven leather uppers, leather soles, and a buckled ankle strap, with enough detail to sit nicely beneath a linen dinner dress. We would also wear them with shorts and a linen shirt for lunch in town.

Saint Laurent Icare Tote Bag in Raffia

If you prefer one generous bag for most of the day, Saint Laurent’s raffia Icare is worth a look. Crocheted entirely by hand, it combines natural raffia with vegetable-tanned leather and an oversized Cassandre logo. Interior ties let you draw in the sides or expand the bag, while a removable raffia sunglasses case keeps a small essential within reach. We would carry it with the linen shirt and shorts for an afternoon in town, leaving room for a book and anything picked up along the way.

During the day, swimwear is generally fine around the beach and pool. For lunch, bring a cover-up or change into shorts and a shirt, and put on shoes before heading to a restaurant. A sarong may be useful by the water, but a dress or an cover-up gives you more options once you leave your lounger.

Dinner is where it helps to check the rules. “Resort casual” usually means a dress, skirt, or lightweight trousers with a top for women, and a collared shirt with tailored shorts or trousers for men. Restaurants with a more formal dress code may require men to wear long trousers and closed shoes. Swimwear, wet clothing, and pool flip-flops are best left in the room.

There is no single dress code across luxury Caribbean resorts, and restaurants within the same property can have different requirements. Check each restaurant you plan to book before packing. For women, flat dress sandals may be all you need for evenings; for men, a pair of linen trousers and loafers can save an otherwise avoidable problem at dinner.

Heavy denim, thick fabrics, and clothes that need constant adjusting tend to earn very little wear on a Caribbean trip. If something feels hot or uncomfortable when you try it on at home, it is unlikely to improve in the humidity. Choose pieces you can sit, walk, and eat in comfortably.

Be selective about shoes. Stilettos are awkward on sand, lawns, and uneven paths, while several pairs of evening sandals take up room without adding much variety. One pair that works with your dinner outfits is usually enough, alongside comfortable daytime shoes and any footwear you need for excursions.

You can also leave behind the separate outfit for every possible occasion. A dress worn to dinner can come out again later in the week, and a linen shirt should work with more than one pair of trousers or shorts. Before packing bulky beach towels, hair tools, or extra toiletries, check what your hotel provides. Save the space for things you know you will use.

For seven nights, aim for three swimwear options, a small rotation of daytime clothes, and three dinner outfits you can wear again. Pack fresh underwear for each day, but give yourself permission to repeat a dress or shirt. This formula assumes you can hang swimwear to dry and rewear clothes that are still fresh.

Wear your bulkiest shoes on the flight, particularly if you need sneakers for excursions. Add activity-specific items only once you know your plans; workout clothes for the gym, or walking shoes for a hike.

Before closing the suitcase, check that every top works with at least two bottoms and that your evening shoes go with each dinner outfit. If something needs several extra pieces to make it work, it is probably the easiest thing to leave behind.

Before you close the suitcase, look once more at the week you have planned. If most days will be spent swimming and reading by the pool, your favorite swimsuit and a comfortable cover-up will get far more wear than a fourth dinner outfit. If you have booked restaurants you are excited about, leave room for something you will enjoy wearing to them. There is pleasure in dressing for a holiday, whether that means a new dress or a linen shirt you bring out every summer. Pack enough to feel comfortable and well dressed, with a little space left for something you find while you are there.