What to Wear on a Tropical Cruise

I’ve rather unexpectedly become a cruise entrepreneur – a career cruiser, you might say. I founded a comedy-and-music cruise called The Atlantic Ocean Comedy & Music Festival, and it’s brought hundreds of people like me – people who’d previously thought themselves more likely to read David Foster Wallace’s writing about cruises than go on one – out to sea. The benefits are many, like hanging out with awesome comics and great musicians, and enjoying unlimited free ice cream. The sartorial challenges, though, are significant. Here’s what I’ve learned.

Dress for formal night. On most cruise lines, one night of your voyage will be designated as a “formal night.” It’s essentially considered a dinner with the Captain, though the Captain doesn’t exactly sit at the head of a 2000-person table. On the relatively (though not extremely) high-end cruise line we use, they suggest black tie. I saw evening formal on women – dresses and gowns. On men, it ranged from real black tie to “my good polo shirt.” You’ll be able to get away with a suit, but honestly? Just go black tie. It’s fun, your date will appreciate it, and it’s nice to have a formal break from the swimsuits on deck. And if you want to do something fun, try a white dinner jacket, like the one I’m wearing above, in the middle of a dance circle that Dan Deacon threw me into last year.
Bring shoes for on-shore and shoes for the decks. You’ll be spending a lot of time in the ocean or a pool, so it’s a good idea to bring shoes appropriate for that purpose. Flip-flops are fine, but think about something a little classier, like leather sandals or espadrilles. They make a big difference. And if you are planning any excursions, remember to bring walking-appropriate shoes. I was glad I brought sneakers when I walked from the docks of Nassau out to the great food spots the ship’s comic told me about.
Bring two swimsuits. If you’ve got a swimsuit rotation, now’s the time to put it in effect. You’ll be in all kinds of water for the duration of your trip. Always good to have something dry when something’s wet.
Bring pants. Even in tropical places, night time is night time. Also: most cruise lines expect pants in the nicer dining rooms. So, unless you want to eat chicken fingers in the “4 Teenz Only” dining room, bring pants.
Keep your palette simple. Blue, white and khaki is a good one. Like any trip, it’s easiest to mix and match. You’ll be glad you brought clothes that are interchangeable through the course of your trip.
Linen is your friend. Linen wears lightly, looks good and dries quickly. A white linen shirt is an easy way to make shorts or a simple swimsuit look a little sophisticated.
Wear something nautical. My friend and colleague Lindsay wore a romper festooned with rope knots and anchors on last year’s cruise. I’m sure she’ll have something just as fun this year. When all’s said and done, it’s a vacation – so have some fun.