What I Wore on My Virgin Voyages Cruise: Over-40, Size 14/16 Packing Guide

I just got back from a five-day cruise to Cozumel, Mexico, and Bimini, The Bahamas, AKA The Riviera Maya, with Virgin Voyages. It was a blast, and I felt I packed very well. I wanted to share what I wore on my Virgin Voyages cruise as an over-40, size 14/16 petite woman.

Why I’m Sharing What I Wore on my Virgin Voyages Cruise

When preparing for my Virgin Voyages cruise, I perused Reddit and YouTube, and searched blogs and Pinterest for outfit inspiration. I found plenty, but little I could relate to. Too young, a smaller clothing size, a different personal style aesthetic. I knew I would have to create a cruise packing guide upon my return, sharing what I wore and what I learned to help fellow soft, curvy grown-ass women find cruise fashion inspiration!

For those who don't know me, my name is Alison Gary. I have been providing real-life style advice at Wardrobe Oxygen since 2005. Prior to starting this over-40 style advice destination, I spent almost a decade as a wardrobe consultant and personal shopper, as well as a visual merchandiser and fashion educator for the retail apparel sphere. I have dressed women ages 22 to 82, sizes 2 to 32, and believe we all deserve to find comfort and joy in our closets.

Disclosure: I was a guest of Virgin Voyages for this cruise. I was a speaker at the Influencers of Midlife Masterclass and received the cruise for free. However, I did pay for my flight, excursions, bar tab, internet, and other expenses. And my choice to write about what I packed and wore for this Virgin Voyages cruise is all my own (you know I couldn't not share!).

What I Packed for My Cruise as an Over-40 Size 14/16 Petite Woman

Since I didn't have to pay for my cruise, I splurged on my Southwest flight and opted for “Choice Extra” to check two bags and enjoy priority boarding. That being said, I over-packed and could have fit all I recommend in one checked suitcase and one carry-on bag. If you are a light packer, I may not be your style, but I hope you still glean some inspiration for your own cruise fashion!

Packing Strategy for Midsize & Plus Size Women

The theme of my packing strategy was comfort and joy with style. As a speaker at a conference attended primarily by fashion and beauty influencers, and as a fashion content creator, I wanted to be sure I was walking the talk.” I wanted complete control over what I wore, so I did not partner with any brands to sponsor any aspect of my trip. I also wanted to wear items I have owned for a long time, and some of you may recognize them, to show you do not need to buy a brand-new wardrobe when going on a cruise.

Fashion Specific for a Virgin Voyages Cruise

Virgin Voyages cruises are different from many other cruise lines. There is no main dining room, and no expectation to dress formally for dinner. Attire is more laid-back, but not sloppy. For example, folks may wear shorts to dinner, but they are linen or chino, not denim cutoffs or rumpled cargos and they are paired with sandals, not flip-flops.

During the day, attire is relaxed but with a touch of polish. While I saw some folks still in their pajamas at breakfast in The Galley (the food court), most folks were dressed for their next activity: activewear sets, swimsuits topped with caftans and cover-ups with more coverage, and casual summer looks from t-shirts and shorts to sundresses and matched sets.

Virgin Voyages also has theme nights. These are optional, but know that the majority of folks who attend the festivities for these theme nights dress the part:

• Pajama Night: Usually the first night of the cruise, you are encouraged to wear sleepwear. This happens at 11pm, so not everyone attends.
• Fancy Night: A night where folks dress up a bit more, anywhere from a sundress to a tuxedo.
• Scarlet Night: A night where everyone wears at least one thing that is scarlet red, the signature shade of Virgin. IMO, if you plan to leave your cabin on Scarlet Night, you will be most comfortable wearing at least a red top or red accessories.

Cruise Wardrobe Essentials for Women Over 40

As a soft curvy woman over 40, I wanted to look fashionable, but I also wanted to be comfortable. Some items I am so glad I brought, as they provided both comfort and joy on my cruise:

• A sunhat I enjoyed wearing. Not too big to wear indoors, but big enough to cover my entire face, neck, and upper back, I wore the “Johvan” from American Hat Makers, which is the hat I recommend in my Starting Style from Scratch series.
• Water-friendly shoes with arch support. I, of course, brought my Teva Hurricane Drift sandals, and they were worn more than any other shoe on the cruise. I also brought these flip flops, which have arch support and are wide-foot friendly. Archies are another alternative for stylish but comfortable flip flops with support. I wore these kinds of shoes in the shower, at the pool, during the day, and on excursions.
• A cute swim coverup. I wanted something that made me feel confident and covered as I went from cabin to pool, grabbed lunch in The Galley, and I could wear when we docked in Bimini, and I visited Virgin's private beach club. I re-subscribed to Rent the Runway and took this dress (also available at Nordstrom with similar concepts at Macy's and Dillard's), which was perfect. Honestly, this dress would also be perfect for evening attire on Virgin as well as daytime style.
• Lightweight mesh bag. For the pool, for excursions, even for grabbing snacks from The Galley or the pizza parlor to take back to my cabin, I was glad to have a lightweight tote that didn't take up much space in my suitcase. I brought this one in particular, which was big enough for my towel, change of clothes, a pouch of personal essentials, water bottle, Kindle or book, and more, while offering a chic pop of color.
• Magnetic hooks. My cabin on Virgin Voyages was surprisingly spacious, offering several hangers, five small drawers, two baskets, a couple of shelves, two wall hooks, and even some storage under the bed. That being said, I owned this pack of magnetic hooks and used them on the metal cabin walls to hold bags and accessories.
• Bandanas. I used bandanas and cotton scarves to mop my brow, to wipe off my sunglasses after a dip in the ocean or pool, to protect my scalp in the sun, tied cowboy style to protect my decolletage, dipped in ice water and placed on my neck to cool off by the pool, wipe sand off my feet before coming back on the boat, and much more. I was glad I brought several.
• Bathrobe. Not just to look cute on Pajama Night, I found having a lightweight robe (this one from Printfresh, to be specific) was nice to put on after my shower to dry off, to wear on my balcony in the morning, to throw on to get room service, or pop empty plates outside the cabin.
• A small battery pack for your phone. If you're using your phone as your camera and camcorder, you may run out of your battery pretty quickly and won't want to go back to your cabin. There aren't a lot of outlets available on the ship; I really was glad to have my iWalk which plugs directly into your phone without cords letting it still fit in your bag or pocket and still be used.

What I Wore During the Day (Excursions & Onboard)

During the day, anything goes, so dress for what you plan on doing. It can be a swimsuit with a coverup, activewear, comfortable athleisure, an ironic graphic t-shirt and shorts, a casual sundress, a stylish matched set… it's all a good fit on Virgin Voyages.

I feel comfortable in shorts, and so that is what I packed and wore. I have a pair of black ponte shorts from Spanx I got a couple of years ago that are a length that prevents chafing but looks modern. I wore them with a striped top one day, and knew they'd also look good with the white linen button-front shirt, the cream and black striped openweave sweater, or the black Chico's microfiber tank I packed.

I packed the palm-print linen shorts and matching cotton voile shirt I got at Talbots last year and wore them one day. I figured the shirt could also work with my white linen pants, but I also packed it just because it's comfortable and I really like it. I packed my matching green Desigual tote not because I needed it, but because I liked the combo.

One day, I wore my bathing suit and the cover-up dress over it because I knew I'd be enjoying the pool. There are no rules on what to wear during the day on a Virgin Voyages cruise.

What I Wore for Dinner & Nightlife on Virgin Voyages

For the evenings, as I mentioned not everyone dresses up, but most do take their casual attire up a notch. I focused on lightweight dresses that would be comfortable in the warm weather and used earrings and other accessories to up the glam and festive feel. Folks wore the same thing at dinner, attending shows, visiting bars, and going to The Manor, the nightclub on Virgin Voyages' Valiant Lady ship.

Pajama Night on Virgin Voyages

For Pajama Night on Virgin Voyages, you will see literally everything. A lot of couples wore matching pajama sets. Some went sexy with lingerie, and some went silly with fleece footie pajamas. One gentleman was dressed like Hugh Hefner, and the winner of the pajama contest wore a sequined dressing gown. The majority of people I saw were in very normal pajama sets – short, long, cotton, jersey, and flannel.

I wanted to make a statement but not feel like I was letting it all hang out. Earlier this year, I got the Printfresh Eco Satin robe and matching jumpsuit in a hot pink and red pattern and knew it would be a great choice. Printfresh is an ethical company that offers up to 6X the cutest and highest-quality colorful sleepwear and loungewear. Also ALISON10 gets you 10% off!

I wore a strapless bra underneath for structure. Since it was a party, I glammed up the look with earrings I already owned that matched, red lips, a red satin eye mask (great to hide humidity hair), and a red fan that I tied to the inner cord of the robe. I received so many compliments and the fabric caught the breeze and made me feel like an Old Hollywood star.

Fancy Night on Virgin Voyages

I bought an orange halter neck maxi dress from COS a couple of years ago. It's a lightweight crinkly fabric with a subtle sheen, and it has pockets. I love it for travel because it doesn't wrinkle, packs up to nothing, and is a breezy caftan or a glam evening look with a change of accessories.

I styled it with bold silver earrings and a silver metallic fringed purse I got at Maje last year (though still available), which I wore as a crossbody. I got the most ridiculous oversized orange glasses at Zeelol last year and added them.

I used Urban Decay's glitter liner in Space Cowboy and added sparkle on my lashline and wore my biggest boldest silver jewelry. But I kept it comfortable with my tomato-red Birkenstock Arizona sandals. No need to sacrifice comfort for style, especially on a Virgin Voyages cruise!

Scarlet Night on Virgin Voyages

Each time I wore red on the cruise, folks commented that I was on theme or early/late for Scarlet Night. I just like the color red, and realized when packing for my Virgin Voyages cruise that I own a lot in my closet and a lot was appropriate for the trip. Needless to say, I had options for Scarlet Night.

You will see folks in red lingerie, in a simple red polo shirt and shorts, in red floor-length gowns, in red devil Halloween costumes, in red pantsuits, in red bikinis and chiffon sarongs, in red cotton sundresses, in red graphic tees and jeans, and everything in between. Folks were ready with red heart-shaped glasses, red wigs, red sequined berets and blazers, and even the Virgin Voyages merch store carries red accessories in case you come unprepared.

I decided to go fashionable but not formal with a red one-shoulder knit top and matching linen wide-leg trousers from Ann Taylor. I already owned fuchsia suede block heel sandals and a matching feather purse, and added them for a fun contrast pop of color. I felt stylish without stealing the spotlight. Here are a few different kinds of outfits I could see be great for us grown-ass women:

• A red striped Breton top with white jeans, red lipstick, and red earrings
• A red off-the-shoulder top with white linen trousers
• A sparkly red caftan from Fringe+Co
• A matched-set top and shorts or top and pants in red or a red print
• A red or red print sundress or shirtdress with a full skirt
• If you already own red satin, sequin, or fringe pieces, bring them!

What I Wore by the Pool & Beach (Swim & Coverups)

Poolside Style on Virgin Voyages

Everything goes poolside on Virgin Voyages. Rashguards with board shorts, full UPF coverage from head to toe, string bikinis, swim dresses, and everything in between.

I felt confident as a soft midsize veering on plus-size woman to wear my bikini, and I didn't cover up when walking to the bar. I wore this cup-sized bandau top from Freya Lingerie with a black swim bottom I've had for a few years. I lay out on a chair with my sunhat, reapplying SPF, and I also ventured into the pool. There were bodies smaller, larger, older, younger, with more and less mobility, and no one batted an eye except at the overly drunk individuals.

Be sure to bring water-friendly flip-flops or slides that are easy to slip on and off. The deck is HOT, and you will need footwear to even venture from chair to pool. Towels are provided and they're extra long, though I was glad to have my towel band to keep it from slipping. Consider a product like Megababe Thigh Rescue to prevent thigh chafing; I applied it in my cabin and brought it to reapply when I visited the restroom.

Virgin Voyages Private Beach Club Style

The beach club is essentially an extension of the ship. A tram/golf cart will take you from the port to the entrance, and once inside, you only need your Virgin Voyages bracelet to buy drinks and get food. Bring the towel provided in your room; they offer a towel exchange so you can replace it if it gets wet or sandy.

I again wore my black bikini, brought my swim coverup dress in my tote, and there I wore white linen pants and a white shirt with my sun hat. I did not need the white shirt and pants. Flip flops would have sufficed. I wish I brought my baseball cap to wear in the water.

I was jealous of those who brought floaties; there was a couple who had what looked to be these and they were perfect in the tranquil waters and wouldn't take up a lot of space in luggage. Next cruise I'm totally taking one and one of these little pumps.

What I Wore on Excursions in the Riviera Maya

We had two port days: one in Cozumel, Mexico and one in Bimini, The Bahamas. I only booked a “Shore Thing,” what Virgin Voyages calls its excursions, for when in Cozumel. The Virgin Voyages app is where you book your excursions, and each excursion tells you exactly what you should wear and pack.

I did the Amazon Secret River excursion, which said all I needed was a swimsuit, change of clothes, water bottle, and optional water shoes. And that was completely accurate. Rio Secreto is the facility that manages the Secret River excursion and it offered optional wetsuits, water shoes, lifejackets, helmets, headlamps, and optional walking sticks. They had every size and were expert in giving you the right fit without any discussion about body size.

I did not bring a change of clothes and wish I did because after the caving experience, we had lunch in a restaurant on the property, then took a 30-minute bus ride to Playa del Carmen to go shopping and explore. I did the entirety of that in my wet bathingsuit under shorts and a linen shirt. Not terrible, but I would have been happier in dry clothing. Trust the Virgin Voyages app to share what exactly you need.

I must say I was glad to have brought a baseball cap, sunglasses, and my mesh tote as I did a lot of walking around Playa del Carmen and a bit of shopping too. I wore my Teva Hurrucane Reef sandals which were perfect for venturing out onto the beach and also walking the streets and going into stores.

Tips I Learned About Packing & Cruise Style as a Woman Over 40

I totally overpacked. Some, I knew I would because I just wanted to have the right accessories for a certain outfit. Some, I just brought too many outfits and felt comfortable rewearing looks. And others, I forgot who I was and dressed to impress strangers, not myself.

• I brought a sundress and a romper that were never worn
• I brought cork kitten-heel sandals that were never worn
• I brought activewear and sneakers that were never worn (I ended up just doing stretches in my room and a helluva lot of walking each day)
• I brought more makeup than I ended up wearing. It was warm; I wore brows, mascara, a bit of a bronzer/blush combo, a touch of concealer, a red lipstick, and one night glitter eyeliner. Nothing else.
• I brought three swimsuits and only wore two (bikini and a tank for the shore excursion)

Cruise Packing Tips for Grown-ass Women

A cruise is an opportunity to dress in a way you can't anywhere else. Go more casual, more colorful, more flamboyant, more minimalistic. Consider it a test drive, or a vacation from your everyday. I took two dresses and a romper I rented clothes from Rent the Runway; this was a lower-cost and lower-waste way to wear fun things I normally wouldn't buy.

Pack comfortable shoes. No one is looking at your feet. One night I wore heels because I was feeling myself, but I had backup Birkenstocks in case. And the other heels, even though half as high, I never wore because it didn't matter. I wore my Teva Hurricane Drift sandals 90% of the time.

Even if you don't eat more than usual, you may find your clothes are tight. More sodium, possibly some alcohol, a change in time zone, there are a lot of reasons why your clothes may not feel the same as they did at home. Prepare for this and leave at home anything that may make you feel restricted or uncomfortable.

Protect yourself from the sun. Bring a sunhat… or even two. I brought two bottles of sunscreen, plus facial SPF, and this Supergoop stick to reapply on the go. I saw folks in rashguards, those hats with the drape in back to protect the neck and back, in zinc oxide, in visors, carrying parasols, wearing arm shields… You will be in good company, and there is nothing that ruins a vacation faster than sunburn.

Packing Hacks for Cruises

For this Virgin Voyages cruise, I flew into Miami and caught an Uber to the port, which was about 20 minutes away. I was able to drop my luggage and check in and get my bracelet (Virgin Voyages use a scanner bracelet for everything from your cabin door to cocktails) but my registered check-in time was a few hours later. By the time I got on the ship, my luggage was waiting outside my cabin door, but some folks had to wait for their luggage.

• Not only do you want your Virgin Voyages luggage tags on your suitcases (print out at home before arriving, they come in your email), but also have sturdy and easily recognized luggage tags with at least your first initial, last name, and phone number. This will ensure your luggage arrives in the right place on the ship.
• Keep your carry-on bag, which should have a change of clothes and basic necessities to freshen up after your travels. In case your luggage is delayed, you can still get in your room and get off the travel sweat and grime. In there have a change of shoes (flip-flops will suffice) and your swimsuit in case you wish to take a dip before dinner.
• Virgin Voyages provides shampoo, conditioner, and body wash in the showers, but I found all three to be drying. Additionally, I'm not comfortable using large refillable bottles in such a communal setting (people can be gross). I love these reusable pouches for TSA-sized toiletries; they have never leaked for me, and some of mine are five years old.
• Bring a reusable water bottle and if you're a coffee fan or want to keep your poolside cocktails cold, bring insulated cups for those drinks. Inside, pack intimates, socks, and other small accessories.
• Purses are good pouches to store jewelry and small accessories. I also put purses inside purses to keep them protected and reduce luggage space.
• Instead of trying to pack my sunhat, I used a Toptote on my carryon bag to secure it. Once on the flight, I disconnected it and placed it on top of the bag under the seat so it wouldn't be crushed.
• Bring a bar of Ivory, laundry sheets, or single-use detergent pouches and handwash in your sink. I handwashed the dress I wore on the flight, used a towel band to secure it to a chair on the balcony to dry, and had it later on the cruise to wear as a swim-coverup. I also handwashed intimates so I didn't have to pack as many.
• Bring at least one fun red thing. A sequined mask, a fascinator, a pair of statement earrings, a bold lipstick. You may find once on board you're feeling more festive than how you packed.

Cruise Wardrobe Tips for Fellow Grown Women

Virgin Voyages does not allow garment steamers, but if you feel you need one, you can request one. That being said, cruises are not a time to look pristine. Pack easy-care fabrics and don't freak out about wrinkles. This is a vacation, not a runway. Yes, even me, a fashion influencer believes that a cruise isn't a fashion show! Have fun, be relaxed and a bit rumpled. You will fit right in.

The ship is well air-conditioned, but outside will be humid. Breathable fabrics and clothes that offer airflow and movement will be your friend. Linen, gauze, cotton voile, and viscose are all good choices.

You can rewear looks. I did, and if I knew how much, I could likely have kept one suitcase at home!

• That orange dress that made such a statement on Fancy Night? I changed into it the last night, styling it more casually with turquoise earrings and my everyday glasses, and I don't think anyone noticed.
• The red dress I wore on the first day I wore for the flight home.
• My white linen pants were worn to Bimini and to dinner the following night. My off-the-shoulder striped sweater was worn with shorts to breakfast one day and with linen pants in the evening.
• And my white linen shirt was worn with the white linen pants, with activewear shorts for my excursion, and on its own for a day at the pool.

Don't try to look younger, cooler, more fun, or more anything than you actually are. The happiest people on a cruise are those who are being themselves. And on a Virgin Voyages cruise, you are celebrated for being exactly who you are.

The key to a successful cruise wardrobe is to focus on comfort and joy. The clothes you bring should be comfortable to wear both physically and emotionally. When you feel good, your look is automatically elevated! If you found this helpful, do let me know in the comments!