R EM E MB ER W HEN B OAT S HOES WERE A TH IN G ? 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.