The Brothers Winchester

Dean, played by Jensen Ackles, is four years older than Sam. He is the quintessential soldier, obeying his father’s orders even when the motives are questionable. Dean has been instilled with a deep sense of responsibility for the well-being of everyone around him, especially Sam; this frequently leads to unwarranted guilt when he is unable to protect innocents and loved ones. Despite these traits, Dean also has a fun-loving, womanizing, pie-obsessed side.

On the other hand, Sam, played by Jared Padalecki, is the wayward son who rejects the hunting life and instead chooses to study law at Stanford University. Although he enjoys a brief period of relative normalcy during college, he learns there’s no rest for the weary Winchesters. Sam’s girlfriend, Jessica, is killed by the same demon that killed his mother. Subsequently, he rejoins Dean on the quest to protect humanity from evil and discovers that he possesses alarming psychic skills.

Despite their differences, Sam and Dean are extremely close. The Winchesters are a formidable team, but their greatest strength is also their greatest weakness: each other. Their foes are quick to exploit this brotherly devotion.Over the course of the show, each brother has sacrificed himself for the other at least once.

Product Information: Jacket, Chambray Shirt, Tiger Shirt, Jeans, Scarf, Ring, Boots, Lip Tint

A life on the road doesn’t lend itself to high fashion. (Though I should note that Dean has occasionally proven to be a bit of a clothes horse..not that he’d never admit it.) When they’re impersonating CIA/FBI/other special agents, the boys suit up (yes, please!) but the rest of the time, they dress down to remain ready for action. At the start of the show, Sam sported typical college-boy hoodies, but his style has since evolved to resemble his brother’s. The two tend to wear layered button downs with jeans, although Dean also has a sweet leather jacket.