As hipsters, rappers, and fashion junkies are decked out like the Kennedys at Hyannis Port, designers are flocking to the boat-shoe-wearing trend. No rendition of the classic sailing shoe is worth walking a wet deck in other than Cole Haan’s hand-crafted boat shoe. When fashion and technology come together, it’s a beautiful thing. In the case of Cole Haan's collaboration with Nike, it’s a comfortable thing. Cole Haan’s Air Blake boasts non-visible NIKE AIR technology in the heel (spring for the current Air Yacht Club Boat; $148). It’s a brilliant rendition on the summer classic. The more salt-stained, the better.