The Finest, Funnest, Most Freeing Footwear

Flip-flops have remained one of the most reviled men’s-wear items. Tom Ford regularly inveighs against them, and fashion magazines make special mention of their ghastliness. But in Orange County, where I’m from, flip-flops function in a way that’s only suggested elsewhere: They complete a tableau of carefree, sand-speckled revelry — an endless, almost utopian vision of joblessness and idle bliss. Even the PacSun and Hollister ads, set in an idealized Orange County, are too charged with a manufactured spring-break debauchery to accurately capture the mellow SoCal lassitude. In the O.C., flip-flops were flimsy foot skis meant to help people reach a secluded surf spot — for hopping in cars or treading lightly atop sand dunes.

Wearers bore them with pride as the sandals bent and warped — like a well-patinaed Barbour jacket or distressed pair of Levi’s 501s — indicating a life well lived. Southern Californians would proudly display their decades-old Rainbow sandals, worn into Paleolithic grooves. There were other, more short-term options: Reefs or Roxys cut in thin black slices of foam for ambling through dingy malls; glossy rubber Havaianas for cruising slightly nicer malls.

Flip-flops were the norm at my SoCal college. On particularly sunny days, campus looked like one giant longboard. When I left for graduate school in New York City, I packed my Havaianas. My mental image of the metropolitan flip-flopper was something vaguely from the early-2000s SamRon-and-Lindsay Lohan era — a certain off-the-rack, louche, bohemian look. Lines from Rufus Wainwright’s song “Poses” came to mind: “Now I’m drunk and wearing flip-flops on Fifth Avenue/Once you’ve fallen from classical virtue/Won’t have a soul for to wake up and hold you.”

Yet, especially once my graduate courses started, I realized I had made a grievous sartorial error. Well-manicured but broke humanities Ph.D. students, often opting for thrifted Issey Miyake or Comme des Garçons, underwent a mini-glitch when viewing my footwear. Even quasi-crust punk philosophy grad students, favoring the urban camouflage of distressed workwear and soiled white tees, seemed to regard them with skepticism. The unwritten rule, I learned, was that the inevitable splash and slime of the city, distributed unpredictably across one’s garments, was fine, to be expected. Having one’s unprotected toes a millimeter from the sidewalk: not so much. In flip-flops, the Southern Californian in New York feels like a waylaid patron of Club Med washed up in a world of impossibly chic, black-clad cosmopolitans.

There are few things more inviolate than a New Yorker in flip-flops. The scrunchie mentioned in a crucial miscalculation by a “Sex and the City” character; a fanny pack or vacuum-sealed dri-fit polo on a wandering tourist; maybe a Rangers jersey. These all pale in comparison to the unbridled disgust one receives from one’s toe cleavage being exposed in haute company.

Eventually, I acquiesced. I tossed out the Havaianas and opted for the sobriety of the loafer or the boat shoe. These were appropriate, dignified choices, I gathered, for going about one’s business during the stifling humidity of New York summers.