The excitement is building — you’ve booked a fabulous all‑inclusive luxury resort vacation in the Caribbean, and now comes the big question: what do you pack? You want to look stylish without overpacking, stay comfortable without under‑packing, and be ready for hot sunny days and cool breezy nights. With a full week ahead, this guide to beach resort vacation outfits will help you build an effortless, affordable, and chic wardrobe from sunrise to sunset.
The focus of your vacation should be having fun and enjoying your time doing the activities you love. Whether its a day at the Spa, Poolside, Beachside, or Excursions, I want to help make sure that you’re confident of what to pack and can instead prepare for your vacation with a clear idea of what types of fashions to wear each day.
What’s on the Itinerary for the Week?…
First step is to review the itinerary. Use the days you’re on travel as a starting point for how many outfits you’ll need to put together. My itinerary normally looks like this:
- Travel Day 1
- Travel Outfit
- Pool Side Outfit
- Dinner
- Vacation Days 2 – 6
- Fitness Wear
- Swimwear
- Casual Wear
- Dinner
- Activity & Adventure Days
- Swimwear
- Casual Wear
- Dinner
- Travel Day 7
- Travel Outfit
Now that we have a rough draft of what we’re doing each day, we can now determine how many of each item we need to bring. So far, looks like we definitely need at least 5 fitness outfits, 6 swimwear attire, 7 dinner outfits, 1 pair of sneakers, 2 casual outfits, and sandals. Pretty simple right?! Yeah it is. Now let’s breakdown the categories.
Your Travel Day Outfit…
Depending on where you are departing, you want to dress appropriate for the weather. My travels to the Caribbean are usually in the Winter. Make sure your travel outfit is transitional from cold to hot. Leisure wear is my go-to. This cute jogger set was warm, comfy, stylish, and transitional once I reached my final destination.
Shop the Travel Day Look…
Chic Swimwear for the Week…
Let’s face it, you can never have enough bathing suits! Whether you’re relaxing in a cabana or sipping a drink on the sand, do it in style with a chic swimsuit. Always go for swimsuits that make you feel comfortable and confident. There are so many styles of swimsuits out there, so grab a few of your favorites to toss in the suitcase!! I noticed in the Caribbean that neon swimsuits were everything! They look good on every skin tone and standout as you sashay around the resort. Don’t be stingy with the swimsuits, you will need them.
Shop Chic Swimwear Looks…
Multifunctional Cover-Ups: From the Beach, to the Bar, to the Bed.
Keep in mind, we want to avoid over packing. Having multifunctional fashions make choosing what to wear easy and increases your options from day-to-day. Most Cover-Up options look like grandma’s moo moo’s or unflattering dresses. I put a twist on my swimsuit cover-ups to be more chic and stylish. Whether sheer pants (picture above), a maxi dress, kaftan or jean shorts, a cover-up can transition you from the water to a luxurious lunch or evening cocktail. And in my case, I purchased Boohoo’s Basic Strappy Maxi dress in multiple colors, using both as a cover-up or a night gown. Check out these smart and affordable options:
Search my picks using code: 5ZPHV. Simply type in the search for products the code.
Resort Evening Wear…
This is your moment to shine! You want to choose outfits that are easy to wear, however when you are at the resort, you will have to be mindful of what type of dress code is in place on the resort. Most of the restaurants are Resort Casual to Elegant Casual but these options below will fit any dress code. I had the most fun planning for this category. I chose easy-to-wear dresses, maxi length, and backless. I also tossed in a metallic pant suit for a more elegant evening on the resort. Remember comfort, as you may go straight from dinner to the dance floor!
Strappy Racer Neck Cut Out Maxi Dress
Casual Looks for Excursions and Adventure…
Here’s a category where you can mix and match, grab and go. Check out my Spring Basics: 10 Must Haves for the Spring and Summer. In my suitcase, these are considered back-ups that I grab for maybe a day at the Spa, a chill day on the resort, or an excursion off site. I pack maybe 2-3 of these items (Basic Tank Top, Denim shorts, Bodycon Dress, Sandals, Sneakers, and Sunnies) and rotate them throughout the vacation.
Resort‑Ready Fitness Wear…
You might be saying, “Girl, I don’t plan on exercising on vacation!” Well, not only are fitness outfits stylish but also versatile. You can wear on a morning walk on the beach then head to breakfast. A day at the Spa, or in my case, to actually exercise for one hour every morning in PARADISE! They’re light weight, compact, easy to throw on, and don’t require much thought. Just thrown them on then go out to enjoy palm trees and a sultry cool breeze, ahhhhhhhh.
The Shoes & Accessories Edit…
Now this category is my biggest strength and biggest weakness. Shoes are very heavy and take up a lot of space in your suitcase. But they can also make or break an outfit. Do you need a different pair of shoes for every look? No! On a resort, all you need is sandals. Whether they are slides, flat sandals or heel sandals, you only need a few to go from day to night. Stick to neutral colors and metallic. These color choices will give you a wide range of options and styles to create. For more dressy outfits, I wear a clear heel. They go with everything! Keep it cute, classy, and simple ladies.
Keep your accessories low. Going from water to land all day every day, doesn’t really call for a lot of changes in your jewelry and bags. Pack your favorite sunnies, a straw hat, a day to evening bag, a dressy pair of earrings, and you’re good to go! Remember, you may go shopping while you’re there, so lets leave some space in our luggage for the memorabilia.
And Most Importantly…Have Fun!
Vacation is a time to have fun! You can incorporate more light, bright, fun patterns and colors into your wardrobe to accommodate the tropical vibes. Don’t get caught up in what to wear and packing lists. Be sure to pack a suitcase full of clothes that feel fun, sexy, flirty and confident. You’ll be all set to have a great vacation at an amazing resort and make memories you’ll cherish for a lifetime. The options are limitless.
A week in the sun is always a reminder that style should feel effortless, joyful, and true to you. Whether you’re lounging poolside, exploring the island, or dressing up for breezy resort nights, these looks are meant to make getting ready feel easy. If you want to shop the pieces I actually wear, you can browse my SHEIN picks using my code 5ZPHV, and explore my full fashion, beauty, and lifestyle recommendations on Benable. And of course, for more daily style moments and vacation inspiration, my Instagram feed is waiting for you at the end of this post.
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