JAMES DEAN

Of the people who have worn a pocket watch, James Dean is the most intriguing. Best known for the iconic film Rebel without a Cause, Dean embodied the outcast he played. So, a pocket watch seemed both out of place with and apropos of his image.

On the set of East of Eden, his breakout film, he would often be seen wearing his gold timepiece, which hung on a chain from his waist. Dean was said to have considered the watch his lucky charm, crediting it with the success he received in his short life. Later, it was gifted to a friend named Tillie Starriet, an older woman whom Dean had taken to calling "mom." After his fatal car crash in 1955, the watch remained largely forgotten until the auction house Antiquorum announced its sale in 2013.

Dean's hunter pocket watch was built in the late 1800s by Standard Watch Co, featuring an Elgin movement and his initials engraved on the lid. While initially estimated at somewhere between USD 5,000 to 10,000, Dean's good luck charm sparked worldwide interest and resulted in bids that ended up at roughly USD 42,000.

WINSTON CHURCHILL

Those who knew Winston Churchill swore that he was rarely without his pocket watch. The "Turnip," as Britain's wartime prime minister called his golden Breguet, always hung across his waist.

Churchill's preference was indicative of his old-fashioned ways—choosing radio over television, for instance—even when modern wristwatches had become the norm following World War One. The chain of his pocket watch was adorned with a case for holding gold sovereigns, a "V" emblem for "victory," two gold hearts that were gifts from wife Clementine, and the image of Napoleon wrought in silver.

Still completely functional, Churchill's Turnip is now owned by his descendants, a valuable keepsake from the man considered one of the greatest wartime leaders of the twentieth century.

This story first appeared in Vault Magazine Issue 17 2014.