Silent Bob
If you’re interested in chain smoking and silence then Silent Bob is your man. The other half of Kevin Smith’s duo, Jay and Silent Bob, he is one of the few people that has managed to make wearing a duster look kind of cool.
Jay
With his foul mouth and fondness of marijuana, Jay made his presence known in many Kevin Smith films as one half of the duo Jay and Silent Bob. His style is much like his attitude, laid back with no concern of what others think about him. Snoogans!
Joan Holloway
The original queen bee of Sterling Cooper, Joan ran the secretarial pool with vicious efficiency. Although men concentrate on her va-va-voom image, she’s smarter than she lets on and isn’t above using sex appeal to advance her career. A smart move, it seems, as she’s gotten a partnership in the firm.
Betty Draper
With her Grace Kelly good looks, house in the suburbs, successful husband and two-point-three kids, Betty Draper was supposed to be the epitome of a 1960’s happy housewife. Too bad she and Don made each other so miserable. However, even after leaving him, Betty still struggles within the confines of conservative suburbia.
Eli Cash
From the Royal Tenenbaums: The crickets and the rust beetles scuttled among the nettles of the sage thicket. “Vamanos, amigos,” Eli Cash (Owen Wilson) whispered and threw the busted-leather flint craw over the loose weave of the saddle cock. And they rode on in the friscalating dusk light.
Phil Robertson
Phil Roberston, better known as “The Duck Commander” is the patriarch of the Robertson family, featured on A&E’s reality TV show, Duck Dynasty. Phil is so devoted to his craft of making duck calls that he even gave up a chance to play in the NFL because it interfered with duck season. With gems such as “She may be an ugly woman but she if cooks squirrel and dumplins, that’s the woman you go after”, who can resist watching to see what he’ll say next.
Jamie Hyneman
Jamie Hyneman co-hosts Mythbusters with Adam Savage, as the more serious and responsible half of the special effects duo. He’s also been a dive master, boat captain, linguist, animal wrangler, and chef, but he’s still best known for looking like a walrus.
Prince
If you don’t think Prince is sexy then you probably haven’t seen Purple Rain or maybe you have no idea who Prince is. If the latter is the case you should Google him now. Considered by some to be the king of androgyny, Prince continues to impress the world with his fashion choices which almost always includes heels.
Joey Ramone
While you might have to make iconic music in order to be as authentically cool as Joey Ramone from The Ramones, it’s easy enough to copy his uniform in order to at least look as cool as him. All it takes is a leather jacket over some jeans and you are good to go, but fronting a band might help too