Women’s Resort Wear: What I Packed for the Caribbean

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Women’s Resort Wear: What I’m Packed for the Caribbean

We kicked off 2023 the best way I knew how: with a trip to the islands with Tommy. While we were sad and a little nervous to leave Thomas (the first time we’d ever both been away from him), I was SO excited for time with Tommy, and I knew we’d both be glad we went.

We had a great time – you can see pictures from our trip here. While we don’t have any other beach trips planned right now, I know lots of people are still planning warm weather trips and visiting resorts so I wanted to reshare this post with some updated resort wear picks.

The first tropical vacation I ever took was to Hawaii as a graduation trip. One of my friend’s dad travelled a ton for work and had so many miles that he was able to fly 8 girls to Hawaii with his miles. So, we just split the cost of a house and it was amazing. The downside? Hawaii was the first beach I EVER visited so all other beaches are a bit of a letdown. 😉 I went to Hawaii a few years later but haven’t been in about 18 years, mostly because it’s just so far from me now. I grew up in Utah so it was a lot easier to get to Hawaii.

Now I’d much rather go somewhere in the Caribbean simply given the easier travel time. (My travel agent LOVES Hawaii so sometime I’ll give her to her wishes that we go there and we’ll tack on a trip there after a Utah visit!)

The other tropical places I’ve been are St. John and St. Lucia, both of which are amazing! (You can read about our St. Lucia trip here.)

Women’s Resort Wear: What I Packed 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 five years ago.

It was so nice to freshen up my “summer” wardrobe a little early and I know I’ll get good use out of those purchases as the warm weather rolls around in North Carolina.

For breakfast and lunch, I wore casual cover-ups over my swimsuit or matching two-piece linen sets, but I also brought a mix of some more dressy outfits that I wore for dinner. When I was shopping for this trip, I was looking for a few tops and bottoms that I could mix and match to create different looks, like a jumpsuit, a mini dress, a pair of shorts and a blouse, or a skirt and a blouse. I wanted to make sure I looked stylish and put-together but still felt comfortable.

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

 bye-bye Thomas

Flowy Dresses

I’m always drawn to airy, floor length dresses when I’m planning for a trip. There’s something special about wearing a light, breezy dress – it’s liberating and comfortable in hot, humid climates. All I need to do is add a pair of sandals and a clutch bag, and I’m ready to go.

I reached out to Revolve when I started packing for this trip because I heard they have a personal shopping service. I sent them my size, the trip details, and even my Instagram so they could see my style. They sent a collection of items back that was SPOT on with my style and the vibe of our trip. I’m linking a few of those in this post!

Tina Midi Dress

This Midi Dress is so cheerful and vibrant. I’m a big fan of bright colors, and this dress has definitely caught my eye. The ric rac straps add a unique touch and make it stand out from other styles. I’m sure this is going to be one of the hottest trends of the year, and I’m excited to see it making a comeback. It’s a great way to add a bit of quirky flair to any outfit. It’s on the pricey-er end of dresses, but it’s different than anything else I have, and I know the quality will be worth it.

De Loreta Dress

I picked up this beautiful blue midi dress at a local boutique right before our trip. I was so excited when I found it since I like to get one new outfit to wear on trips like this with Tommy. Unfortunately it’s not sold online, but if you’d like to do some digging, it’s the same style as the De Loreta Tequila Dress, but in a different print and length.

Letter from TeriLyn January 2023

Anjeli Maxi Dress

I absolutely adore this dress and it would look gorgeous styled simply or with some vibrant, eye-catching jewelry. I’m not usually one for wearing something so exposed, but I feel like it’s appropriate at warm resorts. This dress is formal yet casual enough for the occasion. It’s also and incredibly airy dress that’s lightweight and comfortable, which is crucial when you’re indulging in delicious food on a daily basis.

Alora Dress

I’m totally in love with this long sleeve cut-out dress. The intricate detailing of the dress is simply stunning; it features a deep V-neckline and a beautiful open back with dainty tie-up straps. The fabric is light and airy and perfect for summer days. The tortoise shell ring is the perfect little detail that adds a hint of edginess to the dress. It’s a great piece to dress up or down, depending on the occasion. I was very iffy on cut outs but after trying a few one piece swimsuits with cutouts and seeing how flattering they are, I’m now on board with it.

Lorelei Maxi Skirt and Top Set

I love love love this Petal and Pup set I took on my trip It’s not a dress but rather a crop top and skirt, but it’s definitely fun and it was perfect for our trip. The prices are very reasonable, and I’m wearing an XS in both the top and skirt. I’m fairly new to this brand, but I’ve already found a few really great items. I’m sure this set will be a great addition to my wardrobe!

What Im Packing for the Caribbean

Pink Linen Set

I love matching linen sets! I got this pink set (which you could also pair with matching linen pants or a skirt), but sadly my exact set is now sold out. This Amazon set is VERY similar.


While I already had a few swimsuits that I took on my vacation, I recently came across a few sets sold by Revolve that I absolutely love. The designs are so chic and stylish, and I can’t help but keep thinking about them! I’m really tempted to purchase a couple of them. You can see more of my swimsuit purchases here.

Tularosa Dreamer Swimsuit

I ordered this beautiful suit, and loved wearing it on our trip. 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.

Claudia Bikini Top and Delilah Bottoms

This red bikini top is SO cute. I love the thicker straps and the bright color. The bottoms are sold separately (bane of my existence), but they’re also really cute (but they don’t have great coverage, they’re cheeky!). Since each piece is almost $100, I haven’t ordered them just yet but they’re sitting in my cart.

West Coast Top and Daytona High Waist Bottoms

This bikini top is SO fun. The two colors and the small cutout in the center is calling my name. I typically don’t love bandeau style tops, but I’m drawn to this one since the thin straps make it a little less fussy to wear and worry about falling down. The bottoms that go with it are high waisted, which is flattering, comfortable and on trend.

Lucci Top and Bottoms

This bikini is absolutely STUNNING. The one-shoulder top is so pretty, with intricate detailing and a lovely peach color that compliments all skin tones. The bottoms are just as perfect too, with a flattering fit that emphasizes curves and a comfortable waistband. I already own a dress by this brand and the quality is amazing, so I feel confident that this set is made with the same quality materials and craftsmanship.

Duffy One-Piece

This vibrant chartreuse color is  such a happy color! The cutout pattern is really attention-grabbing and makes this outfit perfect for a fun outing. It’s bold and daring, but still looks age appropriate for someone in their late 30s like me. I’m so excited to rock this look on my next trip! (Hoping to head to the beach again in the early summer!)

Day Sets

Like I mentioned above, I LOVE the idea of sets for this trip. While I could probably get away with wearing cover-ups for breakfast and lunch, I wanted to have a few outfits that are real “clothes” too.

Linen-Blend Ruched V-Neck Set

I recently ordered a floral two piece set from Abercrombie and I’m absolutely in love with the pattern! I decided to go with the the top and skirt combination, and I absolutely love it. This set is now sold out, but Abercrombie is always launching new matching sets, which you can shop here.

Penny Blouse and Tash Shorts

This dark pink blouse and shorts set is bold but not obnoxiously bright. The blouse has a light, airy feel and the shorts are made of a comfortable, stretchy material that’s perfect for lounging around all day. I could easily wear this set over a swimsuit for a day by the pool, or I could wear the blouse with some jeans once I’m back at home. It’s the perfect piece for any occasion!

Comilly Halter Top and Shorts Set

This white halter top is SO fun with the lace up detail. The shorts that go with this set are a longer, tailored style which is a nice change from more relaxed styles. I love the linen material! You’d definitely want to wear a pair of nude undies with these shorts.

House of Harlow 1960 x REVOLVE Quinn Top and Sandra Skirt

I LOVE crochet, and I feel like this set is the perfect way to wear it. I’m not sure when else I’d get to wear a crochet set other than a special trip like this. Shop the top here and the skirt here.

Coverups and Sarongs

I’m in need of a few new coverups, so this trip is a great excuse to shop for them.

Crochet Swimsuit Cover Up

This is from Amazon and I love love love it. It’s so beautiful and higher quality than the price lets on.

Barcelona Dress

This could actually be worn as a true dress if you wanted, but I imagine myself wearing it as a coverup! I love that you could button it up to cover all the way up for a meal, or wear it loose and open by the beach or pool! If you were only going to get one cover-up, I think this is a perfect piece.

Keva Wrap Maxi Skirt

I love this see-through wrap sarong. It’s the perfect material since it’s lightweight but still pretty and makes a chic coverup. It was far too long on me, but if you’re taller, it’s a gorgeous option. You’d wear this with your swimsuit as the top — and I think it’d be cute with a once piece or bikini top.

Shoes and Accessories

Sandals, beach hats, and sunglasses –oh my! Don’t overpack accessories. You’ll only truly need one pair of dinner shoes, one pair of flat sandals (or flip flops), one sun hat, and a few pair of sunglasses (or one nice pair!). You can easily overpack when it comes to accessories like this, but I find that I never need more than just a few pair of shoes and a hat!

Croix Sandal

I love this lace up style sandal. It’s not the easiest to just slip on, but SO pretty, and a great casual option that’s also elevated.

Jeffrey Campbell Rowboat Sandals

This heeled sandal would be a great wardrobe investment, even without this trip planned. A fun neutral summer sandal is essential! I love the raffia material.

Coastal Raffia Hat

I LOVE this black sun hat. I haven’t seen many people wear this color for a sunhat, so I love that it’s unique.

Summer Rattan Bag

This was my most worn bag on our trip. It was the perfect size for holding my beach stuff, but it also doubled as a purse for dinner. You can see the corner of it in the photo below.

Straw Clutch Purse

Since a purse or clutch takes up significant space in a bag, I plan to only bring one. I ordered this affordable clutch from Amazon and planned to wear it with the chain tucked into the purse, as a clutch.

Le Specs Bandwagon 51mm Sunglasses

These affordable sunglasses are my all time favorites if I had to choose one pair. They’re durable and go with everything (and every face shape). You can’t beat the price either!

Anea Hill Manhattan Sunglasses

And since I can’t help myself, I’m also going to pack this pair of statement sunglasses (which are also a personal favorite). They’re pricey, but use code TERILYN at checkout for 15% off  (making them under $200). They’re super high quality, so they’re worth the price.

These are all the picks I’ve got for now. I’ll plan to keep this post updated throughout the spring and summer 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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