The Best Maxi Dresses for a Cruise

A cruise vacation is an ultimate way to de-stress and escape the long, hard winter. However, figuring out what to pack is anything but relaxing. I gave you a few ideas for cruise outfits when I wrote about What to Wear on a Caribbean Cruise.  Here’s one more thing to consider – a cute maxi dress!  Have a look at these fabulous maxi dresses that are ideal for cruising!


Cruisewear - Blue Tie Dye Maxi


Tie-Dye Maxi Dress

If you haven’t bought a maxi in years because you just can’t imagine yourself wearing one to your local mall or out to lunch with a friend, that’s understandable.  However, on a cruise, you’ll feel right at home wearing a maxi dress. Maxi dresses are perfect for sun and sail vacations.

Colorful, breezy maxi dresses like this Olina tie-dye maxi ( above) have an effortless look and feel and give off a relaxed holiday vibe. Complete your outfit by adding some comfy slides, a straw bag, and a small bag, and it’s smooth sailing ahead. This dress would be great by the pool ( it could be used as a coverup for a cruise swimsuit),  for sightseeing, or while having lunch at the ship’s buffet.

Cruisewear - Coral maxi dress styled by Fabulous After 40


Tropical Paradise

One of the joys of getting away in the winter is being able to slip into some lighter colors like this stunning peach coral maxi dress. Imagine what this would look like with even a hint of a tan! This dress is made of jersey, so it falls nicely against the body and has some lovely stretch to it. Plus, the design is really unique.

Don’t you love the shapely front gathering, almost like a sarong, and sexy leg-revealing side slit? To play up the tropical feel, I’ve paired it with a cool straw bag, gold flats, and these very fun earrings. A cruise is a great place to wear bigger earrings than you would typically wear. Dangly earrings are fun and flirty.

Cruisewear - Black and White 2 Piece Maxi dress

Two-Piece Maxi Dress

Here’s an interesting maxi, I have not seen before. It’s actually a two-piece maxi dress – a wrap top and skirt -but it looks like one. This is great for the gal with a trim middle who doesn’t mind a sexy flash of it showing through now and again.  It’s alluring in a classy way.

This would be ideal for a nice dinner on board the ship, and it’s got sleeves, that many maxis don’t!  If you want to wear heels, these chunky sandals are sturdier for walking around in than high, skinny strappy sandals. Flats sandals would be fine too. You see tons of flats on board. It just makes sense.


Cruisewear | Striped Halter High Lo maxi dress

Asymmetrical  Maxi

If you’ve ever been on a cruise, you know, they have casual dinner nights and fancier dinner nights. This pretty, striped maxi is as colorful as a tropical island and would be lovely for dinner in the dining room or at many of the specialty restaurants onboard ships these days.

This type of dress, with the high-low hem, really does look nice with a heel. So you could try something like this nude, low, open-toe pump. A slightly chunkier heel would be fine too.


Cruisewwear Navy and Blue striped maxi dress


Nautical Striped Maxi

You couldn’t get more nautical than stripes, making them everyone’s print for cruising. Stripes are sporty, which translates into fun, energetic, adventurous, and youthful, precisely the look you are aiming for when you travel.

No skinny, too bare spaghetti straps here! Short sleeves give this navy and white striped maxi the coverage you want when you are out and about during the day and don’t want to get too much sun on your shoulders. Rope sandals and a raffia tote with a magnetic snap are perfect for shopping onshore when you have lots of souvenirs to carry in your bag.

Cruisewear - Blue Cold Shoulder Maxi dress


Off the Shoulder Maxi

This romantic blue off-the-shoulder dress by Lily Pulitzer is airy and relaxing, just what you need to settle into vacation mode. Add a pair of lacy, crystal-embellished sandals to dress it up at night when you go for dinner.

Note: be sure to wear sandals before you board the ship. Your new sandals may be a bit tight at first, and you don’t want the crystals on the sandals rubbing against some part of your foot and doing damage.

For more ideas on what to wear on a cruise, check out these ship-shape ideas. And please, let me know if you have worn a maxi on a journey, and did you enjoy it?

Visited 24,317 times, 1 visit(s) today
Join the Conversation

12 thoughts on “The Best Maxi Dresses for a Cruise

  1. 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.

  2. 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!

  3. 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.

  4. 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.

  5. 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.

  6. 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!

  7. 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!

It's your life. Make it Fabulous!