James Franco's big break came in Judd Apatow's lost, lamented teen dramedy "Freaks and Geeks." In a series that masterfully dredged up memories of adolescence's most awkward moments, Franco's perma-baked Daniel Desario managed to look impeccably cool.

Soon the actor will be appearing as a grown-up stoner in the action comedy "Pineapple Express," where he will once again utilize classic rock 'n' roll styling, artfully disheveled hair and a beatific gaze to similarly effortless effect.

American Apparel Organic Fine Jersey Short Sleeve V-Neck: Often described as James Dean-like, Franco doesn't exactly shun comparisons with a personal style that embraces classic 50s cool. ($17.00 from American Apparel).

Levi's Capital E Hesher Straight Jeans: You can't really do this James Dean-via-James Franco look without some classic straight-leg American denim. ($178.00 to $195.00 from Levi's)

Find out more about the Franco look after the jump.

Kings Of Glory Trinity Jacket in Metal: Nothing says all-American rebel like black leather jacket over white T. Unfortunately, nothing says sweat stains and unpleasant odors like a black leather jacket in the summer time. A black nylon or cotton bomber, however, is both badass and practical. ($169.00 from RevolveClothing.com)

AE Leather Eagle Belt: ($24.50 from American Eagle)

PF Flyers Bob Cousy All-American Black: The other vintage, old-timey basketball player-endorsed canvas sneaker: dare we say it, just a little bit cooler than a pair of Chucks? ($64.00 from zappos.com)