Resort wear is the umbrella drink of the fashion world. It should be fun, colorful and a tad sweet. You wouldn’t order a Blue Hawaiian in a Manhattan wine bar. Nor should you wear grays, dark colors or muted prints in Tahiti.
Men’s resort wear is best when cut in classic styles from whimsical, preppy and occasionally loud fabric. The classic lines are important as they keep you from looking like a Day-Glo clad Daytona Beach tourist. The color is important because it keeps you from looking stodgy.
I love the wacky, bright preppy summer clothes of the 1970s. Think vintage Lilly Pulitzer. Or new Lilly Pulitzer. I also like to see a man in seersucker or madras patchworck pants.
I’m not a big fan of shorts. But since most men don’t have the option of wearing a skirt or dress, I’ll give a pass. Beach vacations are exactly where you should be wearing shorts. Pack at least one nice pair. You’ll have room for them in your suitcase once you throw away those jeans shorts, because there is never a time when jean shorts are right. I am an absolute believer that it is possible to wear the right shorts with a shirt and tie, soft loafers sans socks. Really. Meow.
Try on shorts of different lengths. That lingering trend from the 1990s of wearing really long shorts makes most men look as if they have extremely long torsos and short midget legs. This goes for swim trunks as well, the too-long swim suit being the least sexy thing I personally can think of seeing on a toned body. Boo.
Don’t rely too heavily on T-shirts. Boring. Instead pack a few light-colored dress shirts to pair with shorts. This is an easy look for even the most fashion illiterate. Roll the sleeves up to the elbows or wear them unbuttoned with swim trunks.
A lot of men wear golf shirts for dressier resort occasions. I don’t like golf shirts but I recognize their place in the canon of men’s fashion, so I won’t say any more. Except to say that horizontal stripes, especially on a knit fabric, will make you look chubby.
Be sure to grab a tropical tie. And some nice sunglasses. And a summery, lightweight belt.
Ooooh, one last thing: I suggest a banana daiquiri.