I have no idea if David Bailey was actually as coolly and aloofly hip and frisky as the character he inspired in Michelangelo Antonioni's Blow-Up, but let's assume so. After all, he was married to and/or sleeping with the era's great beauties including Catherine Deneuve and supermodel Marie Helvin. But, beyond his personal life, it's his seminal images that he's most famous for, though he did become as much of an icon of the swinging sixties as his celebrity subjects.
If I had about $6,000 burning a hole in my pocket, I'd be tempted to own one of his most famous works, David Bailey's Box of Pinups, a collection of stunning portrait photography of the famous (Mick Jagger), the beautiful (Bailey muse Jean Shrimpton), and the notorious (gangsters Ronnie and Reggie Kray).
I'll also be on the look out for back issues of the awesome and slightly more affordable magazine Ritz Newspaper that Bailey created in the seventies. The little known publication (at least little known today in the US) has been credited by The Times with inventing celebrity publishing. It may sound like a dubious honor, but celebrities were much cooler back then.
Bailey has said, “I've always tried to do pictures that don't date. I always go for simplicity”. He still works in the industry today and is known by admirers as the Godfather of Cool.