Remember when boat shoes were a trend? The finance bro's shoe of choice was all the rage back in streetwear's heritage workwear era, when A.P.C New Standards, chore coats and anything made by visvim were bona fide grails for style-conscious men.

The moc-stitched deck shoe, popularized by labels like Sperry, Timberland and Sebago, has long been a staple of Ivy Leaguers, bankers and other filthy-rich New England types. It's not really the sort of thing you'd immediately associate with streetwear, but aspirational preppy steez has been a cornerstone of street and rap style for decades. Just look at all the times Polo appeared on the backs of hustlers, rappers and gang members.

Pharrell and Kanye were big fans of boat shoes back in the day. Williams was regularly spotted in Band Of Outsiders' Sperry collab back in 2011, and deck shoes were the perfect accessory for Yeezy when he was on his prepped-out, suit-and-backpack tip.

Ronnie Fieg did a ton of boat shoes with Sebago — fringed ones, tasseled ones, ones with chunky Vibram soles — and BAPE even dropped some camo-patterned Sperry Topsiders back when NIGO was still around. Highsnobiety veterans will remember that there was a hyped Sebago, Sperry or Timberland shoe dropping pretty much every week at the height of the craze in 2011.

Needless to say, the hype didn't last forever — the streetwear world quickly moved on to Hood By Air and Givenchy, while the #menswear scene imploded in a shower of double-breasted blazers and embarrassing attempts at pronouncing sprezzatura. 

Yucca Deck Shoes



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You can still find elevated versions of the shoe, though. visvim is keeping the nautical dream alive — deck shoes have been in the brand's collections for years — and this season's version sports OG leather uppers with some calf-hair panelling, for a bit of a luxe bovine flex. Sure, they cost the best part of a grand, but that won't bother yacht owners with a taste for artisanal Japanese menswear.

NYC dadcore staple NOAH recently linked with Sperry, reviving the brand's staple Topsider in a trio of colorways. NOAH's founder, Brendon Babenzien, is as OG as it gets, and much like visvim, his brand is catering to grown-up streetwear kids — the kind of guy that's graduated from hyped sneakers and box logos, and is now looking for something a bit more refined.

GQ hailed the boat shoe as "an inescapable summertime staple if you're a man" (lol), so naturally they're hyped on NOAH x Sperry. Hitting up your local bankers' BBQ? "You'll just instantly be the coolest one there" they gushed.

NOAH and visvim are, by all accounts, great labels, but can they save the boat shoe from its WASP-y reputation? Does anybody want their shoes to make them look like they used to play golf with Dick Cheney? Apart from bankers and GQ readers, obviously.

If you're hell-bent on joining the nautical wave and copping a pair of boat shoes for summer, we recommend you steer clear of any Ivy League clichés, lest you look like a walking Brooks Brothers advert. Slim denim, crisp tees and plain hoodies will keep you on the right side of prep — avoid chinos, knits and fruity colors at all costs.

If you're looking to branch out into some non-sneaker footwear this season and the boat shoe doesn't take your fancy (we don't blame you), then there's plenty of other options to consider. If your spirit animal is a heroin-addled rock star, then look no further than the Chelsea boot. If a Columbian cartel lord is more your vibe, then the loafer is a louche footwear option to consider. Extra points if they're of the Gucci variety. Rock stars and drug barons are much more admirable than finance bros (style-wise, anyway).

Appropriation is what makes streetwear such a fascinating genre of clothing. The culture is built about cultural sampling: take something and make it yours. New Yorkers reworking the Hamptons' shoe of choice to their own tastes — as Ronnie Fieg and Brendon Babenzien have done — is a prime example of the sort of cultural sampling that makes streetwear constantly interesting. Maybe boat shoes don't look quite so #relevant in 2016's climate of high-tech running shoes, but they're a great example of what makes street culture so compelling.

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