T-shirt, $42 by Almond

Cotton bomber, $298 / $150 by Brooks Brothers

Glasses, $75 by Eyebobs

Loafers, $109 by Bass

Chinos,
$68 / $45 by Dockers

James Dean's Lucky Charm

James Dean played by his own rules. When director Elia Kazan told the actor he shouldn't wear his own watch on the set of East of Eden, Dean flaunted the timepiece—wearing it prominently dangling from his belt loop. It was an unusual way to wear such a watch, but this was no ordinary timekeeper. The keyless gold-filled Elgin pocket watch was his lucky charm. Made by Standard USA in the late 19th century (during the heyday of American watchmaking), the then-vintage timepiece was Dean's first big purchase when he moved to New York to pursue acting in 1951. He engraved the watch's engine-turned back with his initials and credited the lucky charm for his quick accent through theater and television to Hollywood. When Dean went to California for his first big film audition, he met with his estranged father, who gave James the gold chain off his own watch to prevent his son from losing his prized procession. Once he became a bonafide star, the young actor gave his lucky watch to Tillie Starriet, a Warner Bros. employee whom he called "Mom," as a token of appreciation for her support throughout his career. And now it can be yours. The pocket watch will be auctioned off by Antiquorum this weekend in Hong Kong and is estimated to fetch between $5,000 and $10,000. The Hollywood heirloom comes with the original fitted box, gold chain and a letter from Starriet attesting to the piece's provenance.

Up for bid on June 22, at Antiquorum