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

I turn 40 this year (!) and to celebrate I’m dreaming of a trip to the Caribbean with my boys. We are heading on a family camping trip to Utah this summer (and bringing the kids), so that will be a great test run. In fact, if we can successfully get a toddler and baby across the country (to a totally different time zone), then 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. I’m re-sharing this blog post towards the end of summer, which means resort wear isn’t the most popular item on retailers’ websites right now. Hopefully my sourcing will help you, if you’re planning and packing for a tropical getaway yourself.

What is resort wear?

Resort wear ranges 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 that 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. You will also want to ensure you 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 a bit of research online to find out the exact dress code for the restaurants at your resort.

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, 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 6 years ago. Alright, let’s get into it. If you’re planning a trip somewhere warm, I hope these ideas help!

Sola Midi Dress

This Sola Midi Dress screams Carribean. The flower cutout, the cotton fabric, and the midi length. Everything is perfect! I love wearing dresses like this on trips because I wouldn’t wear something with such a dramatic cutout at home. This dress would pair perfectly with flat sandals or flip flops. Another reason I love this dress is that it’s under $100. And since the dress already has so much interest, don’t worry about doing your hair. Throw it up in a bun and call it good! That’s the best thing about the beach – casual hair and makeup is the go-to.

White Mini Carolina Caftan

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 Mini Carolina Caftan is a great option (also comes in black). 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. It comes in a long version if that’s more your style, but I have a feeling it would swallow my 5’1″ frame.

Arabela Midi Dress

This sleeveless shirt dress is right up my alley. I love the buttons down the length of the dress (nursing-friendly!) and the belted waist gives it some shape. I’m also always drawn to sleeveless pieces and stripes, so I’m really excited about this find! A dress that’s comfortable, flattering, easy to wear while chasing children (midi length is key), and breastfeeding friendly feels like a major win. I’d style with flat sandals.

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.

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.

Square-neck Linen Set

On the topic of sets, this linen set from Amazon is a must for any beach trip you have on your calendar. It’s lightweight, comes in a ton of colors, and the price tag is really good. A linen set is the perfect breakfast or lunch outfit at a resort. It’s functional but polished, and you’ll feel really cute with an outfit that looks so effortless yet pulled together.

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 sunhat in the airport in order to get it to your destination.

Lavender Crochet Cooper Set

Another set that is perfect for a tropical getaway: this Lavender Crochet Cooper set. The lavender color is gorgeous (I’m having a purple moment) and the crochet detail is perfect for the Caribbean. I love the square-neck top and the mini skirt. You could dress this set up with heels, but I think it would be perfect with a cute pair of lace up sandals (these Samantha sandals are a big hit right now).

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!

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.

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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