I recently attended a Christening on the Connecticut shore. I had packed for the trip quite hastily, and ended up staying three more days than I originally intended.
As such, I found myself shopping near the drawbridge in Mystic – home of the nation’s second-largest stock pile of khakis, topsiders, and silly nylon belts with embroidered sea creatures (which come in adult sizes). The largest is, of course, in Cape Cod.
Luckily, I had packed my favorite shoes of all-time: the 2006 Sperry/Modern Amusement Portofino collaboration. I cannot be evangelical enough about these shoes.
They encompass all the good things about loafers, plus every single good thing about not wearing dress shoes when you travel.
For reasons that I cannot imagine, they discontinued these shoes four years ago, leaving fans to track them down on eBay.
On my third unplanned day on the shoreline, I headed to Watch Hill, Rhode Island to watch the surfers and read on the beach. However, I wasn’t about to take my last pair of Portofinos to the beach and fill them with sand. But would that mean purchasing flip flops?
Flip flops say to the world, "Frankly, I’d rather be barefoot." But they do have a time and a place at locations where it is possible, but not advisable, to go barefoot due to hygeine – in the shower at the gym, or walking around a public pool.
After, I met up with a dinner companion for Lobster rolls at the legendarily laid-back Abbots in Noank. He stopped off to change out of his bathing suit, and returned to the car wearing exactly what any normal person might wear on the Connecticut shore on a beautiful late-spring afternoon: shorts, flip flops and a polo shirt. "Think we’ll have a problem getting in?" he wondered.
We found our way through the massive hotel, and were seated and served right away. I suddenly realized he was dressed exactly as he should be on a weekday beach vacation to the Rhode Island shore.
I looked down at myself in my long pants, button down, and late vintage topsiders, and felt like the prissy city boy in Tom Sawyer, who commits a summertime crime: "He had shoes on – and it was only Friday. He had a citified air about him that ate into Tom’s vitals."
I realized that once you leave most American cities – basically, places you’d never appear barefoot – no one cares what you’re wearing on your feet.
Wearing flipflops in public might still be considered "lazy and ugly." But then, so is reading on the beach and sleeping in a hammock – things I enjoy whenever possible, regardless of context.
Leaving the city probably means that you are seeing something beautiful and relaxing, so who cares whether you’re wearing flip flops or proper shoes?