Southern Conundrum

Should Guys Wear Flip-Flops Beyond a Beach, Pool, or Lake?

Menswear designer Sid Mashburn weighs in on the question of style

An illustration of people wearing flip flops

Illustration: LARS LEETARU

Nothing says Flora-Bama louder than a pair of flip-flops.

I’m a menswear designer and retailer originally from a small town in Mississippi, so don’t get me wrong—I’ve had many a great time down around Gulf Shores. But if you’ve ever been in one of my shops, you’re probably expecting my answer to the question of whether it’s okay to wear flip-flops beyond the water to be a big old heck no. Six and a half days out of the week, I’m comfortably in a coat, tie, and goodyear-welted shoes. Flip-flops, however, are more a state of mind, and I think you can pull ’em off in a way that can feel, against all odds, kinda refined. You’ve gotta be careful, though…in more ways than one. Jimmy Buffett gave us a relatively early education about the perils of the thong sandal, back in the summer of 1977:

I blew out my flip-flop

Stepped on a pop-top

Cut my heel, had to cruise on back home…

We’ve been warned.

I think we listened to that song about eighty-eight times on a five-day weekend at Lake Bruin, in Louisiana, where there was definitely something brewin’. But in addition to not providing much protection from the elements, a flip-flop can look sloppy pretty quickly. And sloppiness begets sloppiness, so when you’re taking the shoes out of the context of a swimming destination, to compensate you’ve got to keep the rest of your look tight. For me, that means a shirt with a collar and clean, well-fitting shorts, jeans, or trousers. No rips, no holes, no pre-distressing, no hems dragging on the ground. And I would limit those bottoms to ones made strictly with plant fibers. Flip-flops and wool never mix.

Hold on—what kind of flip-flops are we talking about? The only two varieties I can really get with these days are super-simple leather designs or rubber ones from Havaianas in Brazil, where they know a little something about the thong-th-thong-thong-thong. We made some great leather flip-flops several years ago at Santa Croce sull’Arno, in Italy—more Galilee than Galveston. WWJW? (The J can stand for either Jesus or Jimmy.) Those options make a pair of trousers more casual in an interesting way. If I’m at the beach for the week and going out to dinner: a chambray poplin shirt, linen pants, and a pair of flip-flops? Absolutely. In fact, I’m pretty sure I wore this exact getup at the Red Bar in Grayton Beach, Florida, with my sisters and my wife, Ann. Today I may even throw on a sport jacket. Imagine Gianni Agnelli in the country and swap out his probable espadrilles for a pair of flip-flops. Kind of elegant, right?

You can dial it back from there, too. Wheat jeans, a sun-faded polo shirt, and a pair of flip-flops will take you a lot of places, close to the water or not. If I’m running over to Whole Foods on the weekend, and my flip-flops are by the back door? Why not? Even though the only water there is canned, bottled, and overpriced. I’m more of a Publix guy, anyway.

So yeah, I’m cool with flip-flops. There have been times when I’ve seen people wearing them and thought, That ain’t quite right, but I guess this is my own change in latitude and attitude, which kind of speaks to the way I experience style. I like different things at different times. We all do. Not sure I’m ready to reembrace the rainbow stacked-sole wedges from the seventies, but who knows? Anything can happen.