What I Wore on My Cruise: Cruise Outfits for Women Over 50

Planning what to wear on a cruise can feel overwhelming—especially when you want to look stylish while staying comfortable. As a woman over 50, I’ve learned that the key to cruise fashion is packing versatile pieces that work from day to night. On my recent cruise, I built a wardrobe around effortless style, wrinkle-free fabrics, and flattering silhouettes. Here’s a breakdown of what I wore and some cruise packing tips you can use for your next trip.
Daytime Cruise Outfits

For days spent exploring the ship or relaxing poolside, I stuck with lightweight fabrics and easy layers. My go-to looks included:
- The pieces I wore from Chico’s in Jamaica were perfect for the cruise. Yes, we actually had a master class while on the cruise that was so insightful.

- Wearing while taking a Master Class: Linen Embroidered Lace Tee with the Brigitte™ Seashell Motif Pull-On Skort that is perfect for a Caribbean cruise!

- This outfit was also featured in my previous post about Jamaica. The No Iron™ Palm Print Linen Shirt over a white Microfiber Tank and the Linen Scallop Hem Crop Pants. Unfortunately, the jewelry has sold out.
- Sleeveless top from Amazon with cropped jeans from Charlie B.

- My travel style consisted of linen pants, a sleeveless pleated babydoll top, and a cashmere wrap from Amazon.

These daytime cruise outfits made me feel put-together without sacrificing comfort.
What to Wear by the Pool

No cruise wardrobe is complete without swimwear and chic coverups. I packed:
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Classic one-piece swimsuit in a flattering cut
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A sheer kimono cover-up that could go from pool to lunch

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Oversized sunglasses and a wide-brimmed hat for sun protection

These accessories made my poolside look stylish while keeping me safe under the tropical sun.
Cruise Excursion Outfits
On port days, comfort was the top priority. For exploring Cozumel, I wore:

- Breathable cotton top with Chico’s Zenergy skort that I wore in Saint Augustine
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Comfortable sandals for walking
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A crossbody bag for sunscreen, phone, and essentials
This casual cruise outfit worked perfectly for sightseeing while still maintaining a polished look.
Evening Cruise Fashion
Evenings on a cruise are the time to dress up a little. I loved wearing:

Chico’s has a wide selection of great maxi dresses for your next tropical cruise. My red floral maxi dress is sold out, but I’ve linked a few dresses that are on sale. Lisa actually wore my Sleeveless Midi Tank Dress for the Scarlet Night Party.

Meeting the Captain and his crew in this Cabana Life Seaside Pique Tunic Dress.


For our final dinner, I wore this Cabana Life Bubbly Cabana Shift Dress. I love the wrinkle-resistant fabric, which is also UPF 50+, making it perfect for a cruise!


Lisa and I wore Soma’s Short Sleeve Scoop-Neck Sleepshirt and Short Robe for bedtime and the Pajama Party.


We celebrated a birthday while on the cruise, and I wore Chico’s Travelers™ Artisanal Chiffon Tunic over the Travelers™ Side Slit Tank and the Travelers™ No Tummy Pants.
My accessories were the Resin & Cubic Zirconia Bezel Bracelet, the Copper Charm Bib Necklace, and Patricia Green’s Malibu Kitten Heel Mule in gold metallic shimmer.
I love Chico’s Travelers Collection because they are travel-friendly pieces that don’t require ironing when you unpack.


Here is another outfit I wore from Chico’s Travelers™ Collection. The Travelers™ Tropical-Lily Midi Skirt and the Travelers™ Collection Tropical-Lily Crushed Jacket went perfectly with the Travelers™ Asymmetrical Top and Travelers™ Classic No Tummy Pants.

My red C.Paravano Women’s Slingback Flats Heels were perfect for the cruise because they were kitten heels. Use my code: ROBIN15%OFF on the C.Paravano website.

By mixing and matching accessories, I was able to create different looks without overpacking.
Cruise Packing Tips for Women Over 50
Here are my top tips for building a cruise capsule wardrobe:
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Choose wrinkle-free fabrics, such as Chico’s Travelers, for easy elegance.
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Pack versatile pieces that can be dressed up or down.
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Stick to a color palette so everything mixes and matches.
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Don’t forget accessories—hats, jewelry, and scarves can elevate even the simplest outfits.
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Comfort comes first—make sure shoes are stylish but walkable.
Final Thoughts
Whether you’re planning your first cruise or your fifth, the secret to cruise style is packing smart, versatile outfits that strike a balance between comfort and elegance. With the right pieces, you can look fabulous at sea without overstuffing your suitcase.
If you’re wondering what to wear on a cruise as a woman over 50, think effortless style, breathable fabrics, and polished accessories—your wardrobe will be as relaxed as your vacation.
Looking to book a cruise on Virgin Voyages? Book here.
Shop my Cruise Style
Until next time!
XXOOXX

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