Channeling a brand's heritage into clothing can work out marvelously (Porsche sunglasses) or tragically (Coca Cola clothing -- for serious, look it up). For gear backed by the OG'est of motorcycle makers, get Indian Motorcycle apparel.
The US's first motorcycle manufacturer (founded in 1901), Indian's seen it all: it's been the world's largest bike-maker, produced two-wheelers for the army, and dominated the racing scene long before the advent of "helmets", or "safety"; production ceased in the 50s, but the brand's just been resurrected -- and they've added clothing to the arsenal. While all the comfortably durable gear has a distinctive moto feel to it (note the six burly leather jackets, including the James Dean-ish "Ranger" and the high-collared "Scout"), it's not all chaps n' studs: there're weathered pima-cotton tees, beefed-up three-button henleys, and crewneck sweatshirts whose tasteful Indian patches'll will make you look tough even as you stagger blearily in your loafers for the morning paper. You can also snag two pairs of jeans, the rugged Hill Climber twill pants, and a smattering of shirts including the twill buttondown Mechanic, one of whose chest pockets gets authentic Indian rivets, locking in your pocket protector like so many gallons of gas
Rounding out the 'cycle theme're two pairs of full-grain leather boots: the mid-calf, buckled-out Biker, and the side-zippered Simple, which owes much of its cred to not being associated with the historically-loathed Complicated.