You’ve booked your cruise, now it’s time to start planning outfits!
From what to wear on a cruise during the evening to how many pairs of shoes you actually need (you be the judge of whether or not I overdid it lol), I’m here to help you plan and prep with cruise outfit ideas so you can look and feel amazing on your vacation.
For this trip I placed a last minute order on Amazon, rented a Nuuly, and also shopped my own closet and I made sure to document the items I actually wore on our cruise.
We went on a seven day cruise to Southern Caribbean islands and also spent two nights in San Juan, Puerto Rico where the ship left from.
Cruise outfit ideas
As a first-time cruiser I had so many questions before we left about what to pack for this week-long voyage.
The category that took me the longest to figure out was what to wear on the cruise during the day, because I knew we would have some all-day excursions that were a combination of sightseeing and some kind of swimming.
Here are some outfits that I actually wore on the cruise throughout the week that I would wear again.
Travel day outfit
A comfy airport outfit—think soft shorts, sneakers, and a breathable t-shirt—is perfect so you can chill by the pool right after you land. It’s casual enough for the journey but cute enough for those first photos aboard the ship.
This worked out well because our trip was in July so it was hot at home and hot in our departure destination of San Juan, Puerto Rico, but if it was colder at home I would have worn leggings and packed the shorts in my carry-on.
My luggage is the Beis medium check-in roller bag and the carry-on roller bag in Atlas pink.
Daytime outfits
Denim cutoffs and swimsuit
This is a classic beach day combo—denim cutoffs and a cutout swimsuit are easy to throw on for excursions or lounging by the pool.
I wore this outfit for our day in St. Thomas, where we took a taxi to Magen’s Bay and spent the day at the beach. It’s an effortless and practical look for days when you’re in and out of the water.
Knit swim cover-up
Swim cover-ups are a cruise essential for moving from the pool deck to lunch without a full outfit change.
It adds a chic layer over your swimsuit and dries quickly after a swim, making it perfect for excursions like snorkeling.
I repeated this knit dress for both of our snorkeling days in St. Maarten and Barbados.
Off-the-shoulder top
An off-the-shoulder top paired with lightweight pants creates an easy but elevated daytime outfit—don’t forget your sunglasses!
It’s great for sightseeing (I wore it exploring Old San Juan when we spent the night in Puerto Rico) or enjoying a sea day brunch.
Swimsuit with patterned shorts
This playful combo of a one-piece swimsuit and patterned shorts is perfect for daytime excursions or simply grabbing a drink at the pool bar. These shorts are by Farm Rio, known for their vibrant and colorful clothing.
I am so glad I wore this for our jungle tour in St. Lucia, where we drove around the island but had the option to jump in one of their iconic waterfalls. The look is functional yet fun for those hot, tropical days.
Dinner outfits
Colorful printed dress
The easiest way to make a statement is with a flowy printed dress—perfect for a cruise dinner or nighttime show.
I loved this Free People one that I rented from Nuuly because the dress itself felt like a complete outfit. Plus, the vibrant colors will make it a standout piece for sunset photos on the ship deck.
Get $20 off of your first Nuuly here.
Midi slip dress
A breezy midi dress is ideal for daytime strolls or casual dinners. The length keeps it comfortable while still feeling polished and great for a night onboard the ship.
I thrifted this one in Beacon, NY a few years back and still wear it all the time!
Mini dress and heels
Packing a flirty mini dress with heels makes for the ultimate cruise night-out look. It’s a fun option for dancing, cocktails, or a special dinner.
This dress is by a brand called Amur and I also wore a dress by them for our wedding reception! They have such flirty and fun styles.
Printed maxi skirt
A printed maxi skirt brings a vacation vibe while staying breezy and comfortable. Pair it with a simple top for a relaxed but pulled-together cruise outfit.
I actually spontaneously cut my tank top in our room on the boat so that the hem would line up perfectly with this beautiful vintage postcard-esque skirt that I rented for the trip!
White linen pants
White linen pants are a cruise essential—they’re lightweight, breathable, and can be dressed up or down. I wore these several times on the trip.
They’re perfect for a laid-back dinner or strolling the ship at sunset.
Day at sea outfit
Exercise dress
For our full day at sea, I slipped into my exercise dress first thing in the morning.
This is a versatile pick for active days on board or even casual exploring in the port. It’s comfortable and breathable, plus it won’t show sweat stains—crucial in the Caribbean heat.
Accessories to pack:
As you’re making your list of what to pack for the Caribbean, don’t forget shoes, hats, sunglasses and bags!
Here’s what I brought on the accessories front:
Sandals
- You may think this is overkill but I brought four different pairs of sandals on the cruise. In my defense, they were all pretty light and I did wear all four pairs! I packed my reliable Havaianas flip flops for pool days, a pair of black slip-on sandals that I could walk in comfortably (similar option here), my new Sam Edelman sandals that I wore most nights to dinner, and one pair of heeled sandals I wore twice for dinner (similar option here).
Sneakers
- I brought two pairs of sneakers on the cruise. I packed my adidas Cloudfoam Sneakers because they’re super lightweight and I wore my Nike Zoom Vomero 5 sneakers on the plane. I wanted to have two pairs because I always wear sneakers on planes and I wanted to have a backup pair in case one got dirty during our excursions.
Sunglasses
- Be proud as I practiced great restraint here and only brought two pairs of sunglasses—one black pair from Amazon (they actually come in a set of two frames!) and one white pair from DIFF eyewear. These went with pretty much all of my outfits and it was easy to rotate between the two.
Purses
- I packed two purses for this trip—one mini Coach bag with a gold hand chain and one Rebecca Minkoff crossbody purse that I have had for literal years and will probably never get rid of. The Coach bag was great for holding valuables when we did excursions and I brought a backpack or tote bag and I brought it to some dinners. For most dinners though, I carried my Canon G7X camera with me to take outfit photos before our meal and my black bag holds the camera nicely.
Backpack/tote bag
- I brought one small foldable backpack as well as a tote bag for the days we had excursions or for when I popped up to the pool on the ship. I didn’t touch the backpack because Andrew also had one, but I used the tote bag pretty much every day!
Any hat!
- My poor scalp was struggling after a few days in the Caribbean sun, so I was super glad that I brought my Met museum baseball cap with me.
Oh and I know it’s not technically a fashion item, but do yourself a favor and pack lots of sunscreen! My favorite face sunscreen is the EltaMD sunscreen and my favorite body sunscreen is the Paula’s Choice one.
Have you ever been on a cruise? What is your favorite outfit or accessory that you brought with you?
yours,
Austen
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