The other day, as I was walking down the sidewalk on a particularly miserable winter afternoon, I saw an old man stepping out for a smoke wearing a chore coat, sweats, and socks with flip-flops. Maybe even just a few years ago, I'd have instantly forgetton what was clearly an outfit of necessity. But it stuck in my craw, partially because of how cool he looked and partially because of how surprised I was that I thought he looked cool at all .
Maybe my brain is broken — okay, my brain is definitely broken — but in an era where every extant fashion taboo was smashed long ago, why not socks and flops? JNCO-sized jorts are good, Y2K-era low-rise is back, and the dogs have long been out, even when they aren't actually out. The flip-flop itself was famously redeemed in 2025. So, why not winterize 'em? Albeit with one minor caveat.
Socks 'n flops is one of the final frontiers of "bad-taste" fashion, up there with cargo shorts and the fake-formal T-shirts sold at Vegas wedding chapels. But when hardly any short remains off the table and it's downright swaggy to rep T-shirts sewn with faux neckties, socks 'n flops is no longer a shock. That's saying something, too, considering that there is no shoe that more overtly demands to be worn barefoot than the thong sandal.
But socks 'n flops is so left-field that it kinda works. They look borderline natural when styled by Stüssy, where they're often juxtaposed with a puffer jacket in a perfect reflection of Californians' godless approach to winter dressing. (even wilder: puffer, long johns, and flops.) And the pairing is only one level removed from toe shoes, another upsettingly emergent inclination that nonetheless makes more sense if only for the simple fact they're actual shoes. Of sorts.
Socks 'n flops were already on the cusp of normalization, an incidental offshoot amidst the overlapping Venn diagrams of Birkenstock's cool-ification and broadening interest in elderly footwear. You could also see the style as a side effect (or symptom) of certifiably edgy fashion pairings like sport socks worn with heels. But socks 'n flops are oil and water, two obvious opposites that only barely make sense as an intentional styling choice. The function certainly does not justify the fashion. But that's fine because when has fashion ever really cared about utility?
Let's say that it's OK to wear this once-verboten combo beyond walking the dog, which it basically is because nothing is off the table nowadays. Should you? Sure, why not. With the proper amount of devil-may-care 'tude, anything can look good. Recall that only a couple years ago, PUMA's superflat SpeedCat shoe was anathema to style. Now, it's the quintessential "cool" snekaer. This is not a matter of the runways saying what's right and wrong, either, because socks 'n flops are a classic eyebrow-raising catwalk styling technique demonstrated by labels as disparate as Kenzo and Acne Studios. But translating would-be trend into reality is the hard part and, let's be honest, this isn't really a look being pushed by fashion brands.
No, in the case of socks 'n flops, it's just a feeling, a sign of the times. And in attempting it, there's a razor's edge between success and, er, flop. It's one thing to wear them to take out the trash. It's another to wear them as a proper look. The trick is to affect the same indifferent ease as an old dude stepping out on a smoke break, for whom socks 'n flops is not a statement but a means to an end, an act of self indulgence. It's just socks 'n flops. Don't overthink it.
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