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

I turned 40 last year, and to celebrate, I just took a trip to Turks & Caicos over the summer (yes, almost a year later, but better late than never). Heather, the world’s best travel agent, handled all the details, per usual, and we booked it with about 6 weeks’ lead time. (That’s not what she recommends, but she can make last-minute trips happen!!) She also planned our honeymoon, babymoon, a trip to Ireland, and, most recently, our anniversary trip to Secret Bay, Dominica. Every time we use Heather, we know the trip is going to be perfect, 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! We are planning a family trip this year soewhere warm and beachy, so I figured it’s the perfect time to share the resortwear pieces I have and love, and some new pieces I just got!

What is resort wear?

Resort attire ranges from swimsuits, coverups, and flip-flops for women 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.

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 closed-toe 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.

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

Pack swimsuits, cover-ups, and elevated outfits for dinner that are breezy for humid evenings. A few dresses and skirts that can be mixed and matched are perfect. I’d avoid denim, mostly because you’ll sweat to death but also because it’s usually not appropriate at resorts. Opt for linen shorts or linen pants instead. (Make sure you have a cute but comfortable travel outfit, too!)

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.

Here are my go-to resort wear outfits with outfit inspo from my recent trip to Turks and Caicos.

White Cotton Eyelet Skirt Set

I picked up a white cotton eyelet skirt and matching blouse last season and didn’t quite know where to wear it – until we planned our Caribbean getaway. It was the first thing I packed. I love a breezy white set like this for resort wear because it feels timeless, polished, and effortless all at once. While the exact pieces I’m wearing here are no longer available, this very similar white eyelet skirt and white ric rac tank capture the same elevated-but-easy vibe. Just add a strappy sandal and sunhat for daytime, then swap for a more structured sandal or kitten heel for evening.

Embroidery Skirt Set

A tank and mini skirt combo like the set I’m wearing below is pure elevated island-girl energy. This Gardenia Sun Vest and embroidered mini skirt is a super fun twist on this look with detailing that feels special, the silhouette is flattering, and the whole look is effortlessly chic for beach dinners or exploring town. I must say, I’m super tempted to get this Folk Flower Embroidered Luna Top and matching Sadie Skirt for a more embroidered, statement-making take on this look. Finish it off with classic sandals for daytime or platform heels like these for an easy night-out moment.

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

Sitano Striped Riga Dress

A classic cover-up is essential for a trip to the Caribbean. Rather than ordering a different cover-up 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 stripe maxi button-down is perfect. It’s ideal to throw on over a swimsuit or transition to an outfit on its own.

Monday Swimwear Montego Mini Tie Dress

The Montego Mini 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. I’m really excited about this Maxi Montego Dress I just got and will absolutely be taking with me on my next trip.

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!

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 them out for 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.

Hill House Crochet Dress

I just got a couple of Hill House resort wear dresses – the Nathalie Dress in Pastel Crochet Knit and the Eliza Dress in Green Dahlia Lace – both are so effortless, feminine, and just super fun. The crochet knit Nathalie feels light, airy, and easy for warm coastal days, so you can wear it as a cover-up or throw on with gold heels for dinner (I’d size up if you’re on the fence). The Eliza Dress brings a more romantic, elevated touch with its feminine lace and flattering silhouette, and I’d say size down if you’re on the fence.

Both are throw-on-and-go styles that feel vacation-ready without any effort – perfect for everything from poolside afternoons to sunset dinners with just a simple sandal (I have these gorgeous platform strap sandals) and a woven bag.

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.

Terry Cloth Loungewear

If there’s one set I reached for on vacation, it’s the Suzie Kondi Sifnos Sweatshirt paired with the Tosk Harem Pants. It’s resort loungewear at its best– plush terry that feels right at home thrown on after the pool or beach, but polished enough to walk around and hang out in before dinner. It’s the perfect in-between piece that makes you feel chic and comfortable (as you should on vacation).

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.

I have to give a shoutout to my favorite swimsuit for moms – the La Blanca swimsuit is my go-to at home – but I opted for more fun ones for the resort because why not?!

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 have a full Left on Friday review linked here.

Left On Friday Peak Swimsuit

I absolutely LOVE this cutout one-piece – it’s the perfect amount of spice while keeping things mom-friendly! If you want a one-piece that is both stylish and supportive, the Peak Suit is my top choice. It has a flattering neckline, a sleek fit throughout, and a cute cutout that gives the appearance of abs (they call this a peek-a-boo), even if you don’t feel like you have abs!

Straw Clutch Purse or Bag

Since a purse or clutch takes up significant space in a bag, I recommend only packing one. I just got this raffia tote that makes the ideal beach bag, but if you prefer something smaller, 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 the 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.

I hope this helped you get excited about your upcoming trip or vacation!

Happy shopping!

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