Women’s Resort Wear: What to Pack for the Caribbean

I turned 40 this past year, and to celebrate I’m dreaming of a trip to the Caribbean with my boys. We had a super busy 2024, so a trip to the tropics didn’t seem feasible, but I have high hopes for 2025. We went on a family camping trip to Utah this past summer (and brought the kids), so that was a great test run. The fact that we successfully got a toddler and baby across the country (to a totally different time zone), means I know we can handle a trip to the Caribbean. That’s one of the perks of living in NC: getting to the Caribbean is not a huge undertaking.

When the travel bug bit me earlier this year, I immediately reached out to Heather, the world’s best travel agent.; she planned our honeymoon, babymoon, a trip to Ireland, and most recently, a belated anniversary trip to Secret Bay Dominica. Every time we use Heather, we know the trip is going to be a knock-out. I’m SO excited for whatever she comes up with this time. One of the ideas she tossed around was Antigua. We shall see! If you want to use Heather, click this link for $50 off your planning fee.

Since I have the Caribbean on the brain, I wanted to share a few resort-wear finds that I’ve been eyeing. Around this time of year (dead of winter), I always start to dream of warm weather once again. I love the winter, and I especially love the holidays, but I can’t help but think about cute sun dresses and sandals.

In this post, I’m sharing the cutest resort wear finds. Many retailers have started releasing fun warm-weather styles, so there are lots of great picks in this post.

What is resort wear?

Resort attire women’s outfits range from swimsuits, coverups, and flip-flops, to closed-toe shoes and long pants for men. There’s a seriously wide range, which is why I thought it would be helpful to explain a few dos and don’ts when it comes to resort wear.

When it comes to the pool and beach area of a resort, swimsuits and coverups are generally considered appropriate. Outdoor bars or casual pool-side restaurants at most resorts will allow you to wear your coverup while dining. However, for most resorts, long pants and closed-toe shoes are required for men when dining indoors, and women are encouraged to wear dresses, skirts, slacks, etc. Resorts almost always list their dress code online so you can plan accordingly.

When packing for your trip, be sure to tell your husband to include long pants and a pair of loafers so that he isn’t turned away at any restaurants. (Duckhead is one of my husband’s go-to brands, and sites like Johnnie O or Peter Millar make great resort options for guys.) You will also want to bring an appropriate coverup so you have something to wear over your swimsuit for pool-side dining.

I like the way St. Lucia’s Sugar Beach resort (where we honeymooned!) explains their dress code: “Resort chic. While jackets and ties are not required, torn jeans, flip flops, bathing suits, and athletic wear are not permitted.” A dress + sandals for you, and a pair of long pants, a golf polo, and close-toed shoes are safe bets for dinner reservations at resorts. Sometimes shorts will be permitted for guys, but you get the idea.

I always recommend doing some research online to find out the exact dress code for the restaurants at your resort. Here are a few snaps from my most recent tropical getaway to Dominica.

Women’s Resort Wear: What to Pack for the Caribbean

For our January 2023 trip, we went to Dominica (not to be confused with the Dominican Republic. They’re different.). It was our first trip without Thomas (and this was before Charles was born), so I ordered a few fun outfits and accessories. It’s also worth noting that I actually did need some new resort wear pieces, since the last time I went to a resort like this was our honeymoon 7 years ago. Alright, let’s get into it. If you’re planning a trip somewhere warm, I hope these ideas help!

White Cotton Eyelet Eve Skirt

I just came across this White Cotton Eyelet Eve Skirt on Tuckernuck’s website and fell in love. Not only would it work well with a white tank and fun necklace for a dinner look, I also love the idea of wearing it as a coverup with a one-piece swimsuit. And since it’s white, you can accessorize a ton of different ways.

You can pair this skirt with flip-flops, sandals, or even a pair of heeled espadrilles.

Nike Red Sanaa Skirt Set

Another fun, resort chic skirt (and this time, a matching top to pair with it). The Nike Red Sanaa Skirt from Tuckernuck screams Caribbean to me. The custom-designed print inspired by ancient architectural patterns is such a fun statement but still very playful. It has an elastic waistline with a tie belt and looks to be really comfortable. You could style this skirt with a simple white tank or tee, or for a more dramatic look, grab the matching Niku Red Muna Crop Top to pair with it.

White Swiss Dot Lee Coverup

A classic coverup is essential for a trip to the Caribbean. Rather than ordering a different coverup for each swimsuit, I like to have 1-2 that I can wear with everything. Since I’m planning a trip with the kids, I’m sticking to Caftan-style coverups, whereas on my anniversary trip, I packed coverups that were a bit more fun. This White Swiss Dot Lee Coverup is a great option. It’s perfect for a coverup and to wear throughout the day over a swimsuit, but I know I’ll also wear it to the neighborhood pool next summer.

Hill House Ellie Nap Dress

If you’ve never tried on a Nap Dress, you have got to trust me and order this. I saw people posting about Hill House Nap dresses for years before I finally got one. What could be so special about these dresses, right? Answer: everything. Seriously, they are the most flattering, comfortable, well-made dresses ever. And I get compliments every time I wear mine. It’s maternity and breastfeeding friendly, doesn’t need a bra, and fits like a glove. You’ll love it for a tropical trip because it’s not fussy, it looks great with flat sandals, and it’s not going to blow up in the wind. Read my full Hill House Nap Dress review here, and order one for your trip here.

Sunset Border Mykonos Dress

I don’t typically go for block print dresses, but this Sunset Border Mykonos Dress is calling my name. I love the bright, happy colors and the shoulder ties. Anything with a bow has my heart. This dress would be perfectly paired with some simple tan flip-flops. This is another one of those “Caribbean dresses” where you immediately know it’s perfect for vacation.

Betty Skirt and Top Set

Sets feel very “Caribbean vacation” to me. Probably because they feel a little too playful and bold to wear in my day-to-day life. But on a tropical getaway? Heck yes. This light pink gingham is fun and feminine, and the cut of the top with the elasticized waistband + midi skirt (with pockets) is just perfect. Since the top and skirt are sold separately, sizing is easier, too.

Navy Stripe Sleeveless Gio Maxi Dress

I saw this Navy Stripe Sleeveless Gio Maxi Dress and immediately thought it would be really cute for your travel day. Since it’s long, you won’t have to worry about a freezing cold flight. It’s stretchy, so it’s comfortable to wear all day, and it’s a good outfit to wear if you need to wear a sun hat in the airport in order to get it to your destination.

Briton Court Savannah Skirt

Briton Court is a newer-to-me brand, and I recently got their Savannah skirt. It’s the perfect maxi skirt for a resort. It comes in a ton of patterns and colorways, and it could be worn with a simple white tank or tee. My current favorites are the Emerald Green and Tiger Ikat print.

Wine Ira Dress

This Wine Ira Dress from Tuckernuck is something I would wear on vacation and then again at home, making it a great investment dress. I love the flutter sleeves, the pastel color palette, and the length. This is just an easy-to-wear dress, and I’m always looking for those!

La Blanca One Piece Swimsuit

If I could convince you to order just one swimsuit for your trip, let it be the La Blanca one piece. It’s the most comfortable, flattering, well-made swimsuit I own, and I hardly wear anything else to the pool. It runs true-to-size and fits every body shape. I’m 5’1″ and love it, and so does my friend who’s 5’10”. It’s almost always on sale on Amazon!

Left On Friday Swimsuit Set

My #1 favorite bikini set for a family trip is by Left On Friday. Their swimwear is super high compression and fits like a glove. You can tell it’s made for you to wear while chasing kids around. I love the Sunday Top and the Hi-Tide Bottoms since they’re high-waisted. I typically wear adhesive Nippies with the top since it’s not padded, and those do the trick.

Tularosa Dreamer Swimsuit

I ordered this beautiful suit, and loved wearing it on our trip in 2023. The pattern and color are very feminine and delicate, with the added touches of ties and ruffles being the perfect details to make it even more special. The high-waisted bottoms are also very stylish and flattering. It’s too revealing to wear at home to our neighborhood pool, but such a cute option to take on a trip!

Straw Clutch Purse

Since a purse or clutch takes up significant space in a bag, I recommend only packing one. This straw clutch from Amazon is affordable and will go with any outfit.

Affordable Sunglasses

Since having kids, I just don’t wear expensive sunglasses anymore. Too risky, knowing how quickly they could break. And when I’m traveling, I also prefer a cheap pair since I won’t be upset if I lose or break them. Since Amazon has such great affordable sunglasses, I ordered a handful this year! I rotate through a few different styles of Amazon sunglasses depending on my outfit. I shared an Amazon sunglasses unboxing and try on reel here. See my Amazon ideal list full of cute sunglasses here.

TKEES Gemma Sandals

If you’re only packing one pair of flip-flops, get the Gemma Sandals from TKEES. The price is great, the quality is perfect, and I love the simplistic two-strap look. I also love that the color of the shoes is close to my skin tone, which is surprisingly slimming.

These are all the picks I’ve got for now. I’ll plan to keep this post updated throughout the early fall with new resort finds. Feel free to bookmark this post for reference later and hopefully you’ll be able to shop some of these on sale (or final sale).

Happy shopping!

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