Hollywood is mourning the loss of Christopher Plummer, who we'll forever remember as the dreamy Captain Von Trapp, as news broke of his death on Friday at the age of 91. The Canadian-born star, whose career spanned nearly 70 years and earned him accolades from the stage to the big screen, became the oldest actor to win an Oscar in 2011 at 82-years-old. And while his celebrated talent and memorable characters are obviously a big part of his legacy, it's also worth noting that the man himself was the embodiment of cool, both on-screen and off. Whether dressed-up and dapper or decidedly rugged with a cigarette in hand, this guy pulled it off effortlessly. And we've got the vintage photos to prove it.

[Photo via 20th Century Fox]