Any surfer worth his wax will tell you those baggy boardshorts that hang down to the shins have come and gone. Go for a shorter style to ease mobility and a bold stripe to increase visibility. Ditch the elastic waistband for one that sits lower on the hips and laces up. Take along a pullover hoodie for when the sun goes down, and instead of flimsy rubber flip-flops, try a more durable leather thong sandal.

Swim trunks by Sundek, $120, at Saks Fifth Avenue. Cotton-cashmere hooded sweater by Autumn Cashmere, $190, at thetannery.com. Polarized Linford sunglasses by Oliver Peoples, $495, at oliverpeoples.com. Burnished leather sandals by Billy Reid, $195, at billyreid.com.