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The Sperry Boat Shoe Renaissance Has Arrived—Heres How to Style Them

Before my secular private school allowed sneakers into the dress code, I wore boat shoes every weekday for four years. I would see them each morning, sitting by my front door, and think of a half-deflated football with that soft, burnished brown leather a sorry contrast to the cream-colored lacing. When they came undone, as they often did due to haphazard tying on my part, the tendrils were rigid enough to coil like unruly horns but were still prone to dragging. I never liked them, representative as they were of the tanned Connecticut country club culture from which I felt alienated as a pale and sickly pubescent. The second I was able, I traded them for New Balances and didn’t think about them again for a decade.

This season, I didn’t pick up a pair of bleach-white suede boat shoes from Sperry by Todd Snyder in preparation for some sailing excursion down my native Atlantic coast, nor was I looking to spend all that much time in the WASP nests of my youth. Truth be told, I was feeling contrarian. I like to dress with a sense of humor, and the prospect of whiling away a Brooklyn summer in a pair of Sperrys amused me, in part because I had just read Bret Easton Ellis’s The Shards and was also considering a pair of Wayfarers (not yet purchased). The joke wasn’t on me in the end, though—the shoe I once considered lame prep is now my summer staple for its supreme comfort and carefree spirit.

Todd Snyder x Sperry Top-sider Suede boat shoe

Starting with color—because Sperry has been around forever, it’s easy for one’s imagination to get stuck in the rut of reddish-brown. The shoe is born anew in ivory, as though washed clean. I immediately envisaged pairing them with some tube socks pulled taut over my calves and up into a pair of similarly crisp linen pants. If going for this white monochrome on the bottom, I figured it would be best to go black up top with a simple T-shirt tucked in and belted. I wore this to work the day I secured the shoes, and felt like Christian Stovitz from Clueless.

My afternoon saunter around Brookfield Place and the North Cove Yacht Harbor that day wasn’t heaven just because I looked good, however, but also because I felt great. Looking out at those boats with the breeze rustling my hair, I felt pulled to leap aboard one and start tying knots and setting sail and the like. It would have been easy because the shoes are so soft and supple and flexible. They bestowed in my step a veritable spring! Before I knew it, I was wearing them all across the city—to pick up my dry cleaning with a pair of track shorts and, yes, high socks; to happy hours galore, always alfresco. They will imminently accompany me to Miami Beach for a travel conference, where I will be quite comfortable moving from my many meetings to evenings oceanside. They peekaboo out of my ballooning black Acne jeans just as well, by the way, lowkey and polite as they are. They can also accompany you, sockless, to the hotel pool.

Sperry Billfish 3-Eye Nautical boat shoe

Make no mistake, the ivory color and suede of the Todd Snyder number are not functional. I lead a life of leisure and have already scuffed mine up quite a bit, in a way that I love because it shows that I’m alive and having fun. If you’re a sailor or actually working on a dock or deck but have come here anyway to get permission to wear boat shoes, be advised that a more traditional option is likely more suitable for you—this guy, for example, will take splashes of salt water much better.

How I’m styling my Sperrys

The location: Around Brooklyn

Abercrombie & Fitch cropped graphic button-up shirt

Todd Snyder Champion Mesh short

Lady White Co. Our T-shirt

Casio Collection A168WG Watch

The location: A work trip to Miami

Scotch & Soda short sleeve linen shirt

Brooks Brothers Modern Pleated chino pants

Ralph Lauren The Iconic Cricket Sweater

Ray-Ban Xan Bio-based sunglasses

The location: At the office

Corridor Canvas Leisure pant

Calvin Klein Supima cotton crewneck t-shirt

J.Crew cotton-blend basket-weave socks

J.Crew Italian leather dress belt

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