Chic Maxi Dresses for a Cruise: Elegant, Breezy & Ready to Sail
When you’re heading off on a cruise, you want outfits that feel easy, elegant, and a little glamorous—without trying too hard. For me, maxi dresses are always at the top of the packing list. They’re breezy and comfortable and help you get into vacation mode whether you’re exploring a port, sipping a cocktail on deck, or heading to dinner.
If you’re wondering what to wear on a cruise that will keep you cool but still look pulled together, these maxi dresses check every box. They’re flattering, travel-friendly, and make it simple to go from day to night with just a quick accessory swap. Let’s take a look at some chic options that are perfect for your next getaway.
What Makes a Maxi Dress Perfect for a Cruise?
Not all maxi dresses are cruise-worthy. The best ones are:
- Lightweight and breathable (think cotton, rayon, or jersey)
- Wrinkle-resistant—you don’t want to iron on vacation!
- Easy to dress up or down with sandals, a wrap, or jewelry
- Comfortable for walking around ports or ship decks
Bonus points if the dress has pockets or comes in a bold tropical print!
My Favorite Cruise Maxi Dresses
Here are a few standout styles that are ideal for cruise life. Many of these are machine-washable, packed beautifully, and flatter midlife figures without being frumpy
Contrast Piped Maxi
Here’s a modern maxi for all my minimalist gals. This all-cotton, contrast-piped maxi is loose, flowy, and incredibly comfortable! You can wear it as a dress or a beach cover-up, but either way, it exudes a clean, sophisticated vibe. I think it looks perfect with these thin two-strap sandals, which mimic the piping down the front. Sometimes, less really is more.
Check out these other ship-shaped ideas for what to wear on a cruise. Please let me know if you have worn a maxi on a journey and if you enjoyed it.
Palm Leaf Maxi
If you like tropical prints but find most of them too wild and colorful for your taste, then this Hawaiian Kalaini maxi dress is for you. It’s fun and exciting, but the simple brown and cream palm leaf print keeps it grounded and easy to wear.
Satin Floral Maxi
Some nights on board a cruise ship is designated dressier than others, and that’s when a satin slip maxi dress is a great choice. This gorgeous, slinky maxi dress for a cruise dinner is perfect for the occasion. It has tiny spaghetti straps, an alluring cowl neckline, and a sleek, sexy fit. Here’s a similar satin floral maxi in lighter colors. Are you wondering about a bra? I love the Wacoal Red Carpet Convertible bra ( strapless) to keep the girls in place.
Breezy Halter Maxi Dress
One of the joys of getting away in the winter is being able to slip into lighter colors, like this dreamy green floral print maxi. It’s such a fresh summer color, and the washed print gives this breezy halter dress a soft, lovely, artsy vibe.
These chunky woven straw sandals are right on trend and very practical for walking around on a ship. The neutral color is a perfect choice because it doesn’t compete with the dress for attention. Add a straw bag and a touch of jewelry, and it’s smooth sailing ahead.
Scarf Print Maxi
Breezy is beautiful when you are strolling around on deck, and the sea air is blowing through your hair. This elegant Scarf Print Maxi is light and airy, making it a perfect look and feel for a cruise vacation. I love the modern mix of florals and stripes, as well as the understated combination of light blue and cognac. Beautiful!
Tiered Yellow Floral Maxi Dress
Hello yellow! Here’s a cheery-looking maxi sundress that screams ‘vacation’ to me. The bold pink and blue blooms against a yellow backdrop are fresh and feminine. I like the way this Yellow floral maxi dress is tiered without looking flouncy and boho. Elegant and Ladylike!
Cruise Style Tips for Maxi Dresses
- Throw on a denim jacket or a lightweight wrap when the air conditioning blasts inside.
- Keep your look polished with simple accessories, such as gold hoops, a straw clutch, or a pop of color sandal.
- Bring dressier sandals for evenings and flats or wedges for day outings.
Bon Voyage!
A maxi dress is one of the easiest ways to feel confident and comfortable on a cruise. You don’t have to overthink your outfits—you just slip one on and go. And with so many flattering, modern options out there, you can find one (or two!) that suits your style and keeps you feeling fabulous at sea. Bon voyage!
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I love the looks and feminine aspects of the outfits.
What are the best cover-ups to wear with the maxi dresses? I have a similarly stripped maxi, and sometimes I get chilly. I have a black crop 3/4 sleeve sweater, but it seems too dressy for the striped dress. Thank you.
Hi Rose, Have you thought about a denim jacket, white or blue? This post may help: http://bit.ly/2171oh7
On a recent cruise to Greece and Turkey, I took three maxi dresses (one was the black and white stripe!). They were indispensable! I was relaxed and comfortable for daytime tours and added a shrug to cover bare arms when needed. They were also perfect onboard the ship at poolside and dinner!
The outfits are great, but flat sandals for us over 40 ladies for walking around all day? Even 20-somethings need some cushion in footwear if they walk all day.
I LOVE maxi dresses and can’t wait for the weather to warm up enough to start wearing them!
Does anyone know a good place to buy petite maxi dresses? Thank you.
I love the outfits you put together! Maxi dresses are a godsend. My legs are victims of KP, and I rely on maxi dresses to stay cool in the summer, and they look great. I have several, and I also have maxi skirts. My go-to is a maxi skirt + tank top+statement necklace+jean jacket and flat sandals. I hope these maxi dresses stay in style forever.
Maxi dresses are my favorite thing in the world to wear. I will be 50 in a couple of months, and while it is necessary to find the right style to flatter one`s body shape, they are versatile, comfortable, feminine, and timeless…need I say more, lol? We are in mid-autumn here in New Zealand, and they are perfect for this time of year.
I love your website, Deborah! On behalf of all 40+ women, thank you for this continuing resource.
I would be thrilled if you offered some suggestions on places to shop as one’s figure continues to change (thickening waist, “bat wings” under the upper arms, and so forth).
Regarding the maxi dresses and many other dresses and tops that you profile, I wonder if you could consider those of us who are unfortunate enough to have aging upper arms that we’d instead not showcase? The sleeveless look isn’t for all, and it would be great to profile sweaters, jackets, scarves, etc., that provide upper arm coverage.
Again, thanks for all your work to support 40+ women!
Hi Roxie. I’m touched. Thank You for your lovely compliment! I posted on maxi dresses that cover your arms, so look at this and see if there is anything you like.
I’ll work on more posts about coverage too! Cheers, Deborah
I love both of these looks. I have two questions, however,
While I love the idea of a maxi dress, and I love how it looks on models and on other people, I always look dumpy and short when I wear one. Flats make me look dumpy too. So what to do? Wear heels? That’s uncomfortable when doing a lot of walking. Get the dress shortened? Even when I do that, I still look dumpy when the dress hits my ankles. How short to go without defeating a maxi dress’s whole purpose (comfort!). I’m 5’4″
Second question. The blue/white look is adorable. However, whenever I wear a separate top and skirt or pants with a belt that doesn’t have any belt loops to go into, the belt rides up when I sit down, and the shirt pulls out and loops over the belt. When I stand up, I have to re-adjust the whole thing. Unattractive and sloppy! What do? I do want to know!