As the star and director of Easy Rider in 1969 in a role that made one critic say "no other persona better signifies the lost idealism of the 1960s than that of Dennis Hopper," the star was on everyone's radar in the '70s. Between this huge role at the beginning of the decade and his attention-grabbing performance in 1979's Apocalypse Now, Hopper strutted around Hollywood in rebel Western garb that originated during his upbringing in Kansas and Missouri.

The urban cowboy aesthetic was hugely popular in the late '70s and early '80s, and Hopper was definitely one of the main catalysts for this nationwide trend. We wouldn't recommend rocking cowboy hats in 2013, but back then Hopper was mining a look that was unique and naturally worked for him, and Western gear is definitely having its moment again. If you can look as good as this OG, then go for it.