Don’t sweat it — sock it. We met with Natalie Cantell, Nicole Kliest, Jian DeLeon, and Brian Davis to see why they are fans of socking it up.

Moving to New York from Sydney many moons ago shattered more than one of my once tightly-held beliefs. I learned that the correct way to eat a slice of pizza is to fold it in half to create a sort of “pizza taco.” I learned that the acceptable number of floors in a building without an elevator is six (legally, at least). And I learned that while my strict “bare ankles 4eva” style philosophy was cute, it sure was impractical for a good chunk of the year.

I’d been living my life thinking my most effortless outfits relied on a breezy little flash of skin north of my footwear, but (cue Cher Horowitz voiceover)… did they? Was I simply stuck in my ways? Had I been stupidly denying myself the charm (and warmth) that came with the addition of a pair of socks, perhaps in a crisp white or a subtle houndstooth? If I wanted my favorite NYC-friendly footwear—from low-top sneakers to chunky loafers to classic boat shoes—to have a moment to shine between November and March, it was time to get with the program. With the abrupt realization that I’d never actually experienced winter (or even a convincing fall), chilly temperatures bumped me and my once-bare ankles firmly over to the cute and cozy world of #TeamSocks. And I haven’t looked back.

— Natalie Cantell, @nataliecantell

Natalie Cantell is the Executive Director of Who What Wear Brand Studio.

 

No offense to ankles but there is nothing that tickles my fancy quite like a well-styled sock. To think that for so many of my adolescent years I was hoarding an ungodly amount of ‘no-show socks’ in some misguided attempt to pretend my skin didn’t desire the soothing texture of a cotton sock (the horror!). I’m older and wiser now and am rooted firmly in the pro-socks category of human.

For starters, socks are comfortable and feel nice to wear—we’ve established that. But in terms of personal style, wearing them is a low-lift way to make a statement. For me, that statement is a mix between French-inspired dressing and something that, say, my grandpa might wear. Slouchy sleek.

I know what you’re thinking. Would you actually wear socks with boat shoes on a sea vessel, Nicole? No, probably not. But I live in New York City where the only boat I’m stepping on is the IKEA ferry once every nine months (or longer if I can manage). I wear my boat shoes for the mood they emit. Elegant, sophisticated Americana vibes that blend in well with my wardrobe of classic staples. And the socks? I add those in for that evasive quality of unexpectedness and effortlessness that can sometimes feel hard to nail down.

Winter, spring, summer, or fall—they’re relevant any time of year. If your outfits have been lacking that extra oomph lately and you’re ready to make a change, might I suggest you begin with a sock?

— Nicole Kliest, @nickliest

Nicole Kliest is a freelance writer and editor based in New York City with eleven years of experience in the digital publishing industry. She is an enthusiastic storyteller who enjoys travel, food & wine, interior design, fashion — and the people who exist within those realms.

I wear Sperrys year-round. Most people might think they’re purely a Spring/Summer shoe, but the siped sole actually gets decent traction in colder weather and icy or wet conditions. After all, that exact terrain inspired their invention. But I’m not going sockless in winter, which is why I usually wear my A/Os with an athletic sock. I’m almost always in some version of the breathable, versatile sock.

I’ve resigned myself to the fact that I will probably never wear these shoes on a boat. But even if I do, I can’t see any reason why I wouldn’t be wearing socks. Am I gonna go for a swim? Then I’ll take my shoes and socks off. What if I fall off the boat? Well, if the rest of me is soaked, I can’t imagine I’d be thankful that my ankles have one less layer of fabric around them. Basically any fit I have in my head with boat shoes usually has socks in it, and almost always a trouser.

In some ways, I characterize the boat shoe as an alternative version of the oxford. I wear mine with suits, jeans, and even sweatpants if I find myself going on a quick bodega run—or if the sweatpants are nice enough, which in 2022, I think is safe to say that universally accepted luxurious iterations exist. And you can be absolutely certain I’ll be wearing them with socks.

— Jian DeLeon, @jiandeleon

Jian DeLeon is an editor, writer, and creator based in New York. He edited two books for Highsnobiety: The Incomplete Highsnobiety Guide to Fashion and Culture, and its follow-up, The New Luxury. He is the co-founder of Muleboyz, an Instagram community built around a shared enthusiasm of backless shoes and clogs. He works in the fashion industry.

“Is something ever so wrong, it’s right? If there were ever a sartorial move that could evoke such an immediate, impassioned, and visceral response – the debate of socks with boat shoes might be at the top of the list.

There’s no gray area on the topic. You’re either in camp no sock or the presumably smaller camp pro sock. I’m not sure if it’s my natural contrarian ways or maybe just that I like to zig when everyone else zags, but the mere fact that the idea of socks with boat shoes is so controversial and off-putting to the majority of people makes me want to state an argument for it.

First things first – no “fun socks”. This is not a time for stripes, argyles, or novelties. Grab a crisp pair of white cotton socks and wear them with your favorite chino shorts (cut above the knee!) and pair with a worn-in polo, rumpled oxford cloth shirt, or breezy patch madras.

For a cooler day, substitute the shorts with a pair of chinos (not too slim, not too baggy) or lighter wash denim like a broken-in 501, and a vintage military shirt, cotton sweater, or chore coat.

At the end of the day, socks with boat shoes is a choice, not a necessity. Everyone knows boat shoes work well with no socks at all, but why not live on the edge, take a chance, and try something different – I’ll be right there with you.”

— Brian Davis, @woodensleepers

Brian Davis is the founder/owner of Wooden Sleepers, a New York-based vintage American menswear brand, online store, and showroom.