
He’s the quintessential crooner, the Sultan of Swoon and one of the sharpest dressers of his era. Strangely enough though, Ol’ Blue Eyes didn’t show off his string of number 1 hits on his wrist. In fact, mob connections aside, his watch action was rather subdued.
Sharp as his classic look was, Frank Sinatra eschewed the usual Patek and Vacheron dress watches of the elite in favour of a more unusual choice. His first watch in fact was a relatively sober pink gold Gruen, a company that went defunct around 1958.

Frank Sinatra’s Gruen Watch © Paul Boutros (TimeZone)
It was a decent watch but nothing flash, perfect for a boy from New Jersey just starting to making it large. And hey, at least Sinatra bought American. The watch got more interesting though when he passed it to his friend Al Silvani, the trainer of Rocky fame, complete with “To Al ‘Flight over America’ Frank Sinatra Hollywood 1945.”
Frank’s second watch was actually a gift and far more in keeping with his sartorial stylings. Ava Gardner, his second wife, bought him a yellow gold, silver dial Lucien Piccard. The brand still exists, but not quite in that kind of style any more. Think more openworked dials and almost too much detail for the eye to handle.

“Stranger” Musical Watch by Ulysse Nardin
All in all Sinatra’s own watch game wasn’t that on point, unlike his dress sense. That hasn’t stopped him influencing watches today though, at both ends of the horological spectrum.
On one, you have Ulysse Nardin’s Stranger, a music box on the wrist that played – you guessed it – Strangers in The night. It’s still one of the oddest pieces that Ulysse has produced, and they’ve made the Freak.

Raymond Weil Frank Sinatra Limited Edition
On the other hand you have Raymond Weil’s tribute. The Frank Sinatra Limited Edition was actually one of their earlier ones, though they’re all but innumerable now. Designed with the Sinatra family and released for what would have been Frank’s 100th birthday, it was a fair interpretation of one of the most legendary figures of stage, screen and sound.
Though his horological heritage may not stir the loins of watch lovers the world over, at least he did it his way.