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

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I turned 40 last year, and to celebrate just took a trip to the Turks & Caicos (yes, almost a year later, but better late than never). We went on a family camping trip to Utah last 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, and my trip to the Turks was no exception! If you want to use Heather, click this link for $50 off your planning fee.

Resort wear hasn’t always been easy for me because I’m more of a mountain person, but this time I feel like I had the perfect resort-worthy wardrobe! And since I have the Caribbean on the brain, I’m sharing those pieces (and more) that I absolutely loved and brought with me!

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 some 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 recent trip to the Turks and Caicos.

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

White Cotton Eyelet Skirt Set

I got this white cotton eyelet skirt and matching eyelet blouse a couple months ago and didn’t quite know where to wear it. But when I decided on the Caribbean for vacation, it was the first thing I thought to pack! It’s breezy, timeless, and effortlessly polished. It feels elevated but easy, and the matching set makes getting dressed a no-brainer. Just add a strappy sandal and a sunhat for the day or a more structured sandal or kitten heel for the evening.

Embroidery Palm Set

The brown & cream embroidered palm tank and matching mini skirt gives elevated island girl energy. The embroidery feels special, the silhouette is flattering, and the whole look is effortlessly chic for beach dinners or exploring the town (if you’re around one). It’s the kind of set that turns heads without even trying. Pair with classic sandals or platform heels like these!

If you’re on the hunt for some good sandals, I put together a list of my favorite neutral sandals here!

Blue Stripe Griffin Dress

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. You can’t go wrong with a button-down coverup and this blue stripe maxi button-down is perfect. It’s ideal for a coverup to throw on over a swimsuit or transition to an outfit on it’s own.

Monday Swimwear Montego Mini Tie Dress

The Montego Mini Tie Dress is effortlessly chic–the kind of cover-up that makes you feel put together with little effort. I wore it in Turks over the Seychelles bottoms and Aruba top bikini, and it instantly pulled the whole look together. It’s feminine, light, and just the right amount of flirty for going from a beach day to sunset cocktails.

Marea Sasco Dress

The Marea Sasco dress was perfect for dinner in Turks–flowy, romantic, and just the right amount of dressy without trying too hard. The print is stunning, and it moves so beautifully. It’s also one of those pieces that instantly makes you feel pretty. I threw it on with sandals, but you could easily throw on any of these white sneakers for a casual daytime look!

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.

o.p.t Ridley Linen Dress

The O.P.T. Ridley Linen Dress was such an easy, polished look for daytime in Turks–but it totally has that day-to-dinner magic. I wore it with sandals to explore during the day, but if you swap in a heeled sandal like these, it’s instantly dinner-ready. The linen keeps it breezy, and the accessories shift the tone to whatever look you’re after.

Love the Label Nylah Skirt Set

The Love the Label Nylah Skirt and matching Cassia top is so fun and flattering–it’s bold and playful but still super wearable. I love it as a matching moment, but the skirt would be just as cute with a simple white tank or tee if you wanted to mix it up. It’s one of those sets that gives you options but still feels like a statement. I paired it with these gorgeous platform strap sandals!

Scoop Neck Maxi Dress

This sleeveless maxi dress is daytime perfection– breezy, comfy, and so easy to throw on and go. I wore it to brunch in Turks and felt totally relaxed but still cute. The fit is super flattering, it has pockets, and it could easily double as a beach coverup too. Just one of those under $40 gems you’ll end up living in.

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!

Summersalt Sidestroke Swimsuit

The Summersalt Sidestroke Swimsuit is one of those magical suits that just works– flattering, supportive, and somehow makes you feel amazing no matter what. I wore it in Turks and loved how secure it felt– I even felt bloated and was shocked because you couldn’t tell in this suit. The one-shoulder style adds such a chic touch too!

I also wore and love this seascape sweetheart swimsuit from Summersalt – the coverage is perfect and I also just love the material. I put together a roundup of the most flattering mom-friendly swimsuits in this post.

Stylest Dreamsculpt Square Neck Suit

The Stylest DreamSculpt Square Neck Tank swimsuit is such a flattering classic– the square neckline and sculpting fabric make it feel super sleek and secure. I wore it in Turks and loved how confident it made me feel, and if you throw on the DreamSculpt Swim Belt, it instantly gives it that extra styled-up look. So good for when you want a little more polish by the pool.

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. I also LOVE this cutout one-piece – it’s the perfect amount of spice while keeping things mom-friendly!

I have a full Left on Friday review linked here.

Straw Clutch Purse

Since a purse or clutch takes up significant space in a bag, I recommend only packing one. This year I brought this raffia mini bag, which is unfortunately sold out, however I love (and in the past, have always brought) this straw clutch from Amazon which is so affordable and will go with any outfit.

Affordable Sunglasses

Since having kids, I don’t really wear expensive sunglasses anymore (with this exception of these Warby Parker sunglasses). It feels a little 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. I often rotate through a few different styles of Amazon sunglasses depending on my outfit. I shared an Amazon sunglasses unboxing and try on reel here. I’d grab these neutral ones if you’re only getting one pair. And if you are willing to spend a little more on sunglasses, I recently got these classic rim sunglasses– they have become my go-to sunnies!

TKEES Flip Flops

If you’re only packing one pair of flip-flops, get the Lily Nudes Flip Flops from TKEES. The price is great, the quality is too! I will say, I got the Amazon version of the TKEES flip flops, and actually might like them better– the TKEES are super thin and whereas the Amazon ones are more cushiony! The color of the shoes is close to my skin tone, which is surprisingly slimming.

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), since we’re approaching fall!

Happy shopping!

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