Undeniably, fedoras can be one of the most affected things a man can wear. Anyone who wears one would probably admit to liking the cocksure look of a fedora more than the actual function of one: Sun shield? Hair-loss hider? But fedoras are also the ultimate test of individuality. You just can't pull off wearing one unless you are unusually confident, daring, and nonchalant. All that said, men who sport hats of any kind can get away with just about anything as far as I'm concerned.
This May at the Costume Institute benefit at the Met, where women parade around in couture like pretty peacocks and men serve merely to escort them, I walked away from that evening realizing that the person who had stunned me was Nick Cannon, an MTV host and movie actor. He was wearing a traditional black tuxedo, white shirt, and long black silk tie (secured in a thick Windsor knot—bonus points for that) and above all, he topped the whole look off with a sleek black-felt fedora. He was elegant, a little bit street, and sexy all at the same time. His look reminded me of a Bing Crosby photo from the sixties that I have long admired. A male friend asked me recently if I would ever want to make out with a guy in a fedora (were I not married, of course). And my answer was a resounding yes, given that the hat came off first. I'd never heard of Nick Cannon before the night of the Met Ball, but you can be sure I'll pay attention whenever his name comes up now.
Nick Cannon (with Selita Ebanks) at the Costume Institute Benefit at the Metropolitan Museum of Art, May 2007. (Getty Images; May 2007.)
Bing Crosby, pairing a fedora with a tuxedo in the 1961. (Getty Images; January, 1961.)
Sam Buffa, the co-owner of Freemans Sporting Club barbershop and also a member of the U.S. national motocross team, sporting the straw fedora that he almost never takes off.
A groovy Williamsburg dude, adopting a surprisingly conventional look. The striped ribbon keeps it from looking too straightforward. McCarren Park, Brooklyn, July 2007.
Brigitte Bardot with her then husband Gunther Sachs, in 1967. You can't do much better than that. Deauville, France, 1967. (Roger Viollet/Getty Images; January, 1967.)
Sunday Best at its best. Kansas City, circa 1955. (Getty Images; January, 1955.)
This guy is borderline too hipster for me: It's all a bit too cool for school. He pulls it off though. Just. Houston Street, NYC, 2007.
There's no question that Mick and Keith (captured here with eternally cool Anita Pallenberg) were trying very hard with their fedoras. It doesn't matter though. They look amazing, and they've got style to spare. Heathrow Airport departure lounge, London, 1968. (Getty Images; December, 1968.)
What I like about this guy is that he reminds me of someone working in an Italian meat shop (think Satriale's from The Sopranos) in the 50's. He looks authentically old-school even though he actually works the counter at Magnolia Bakery, a cupcake shop in the West Village. Bleecker Street, NYC, May, 2007.
I think this man looks cool in a very unassuming, unpretentious way. My editor at Men's Vogue, however, remarked that he could either look like a horse trainer at an English racetrack (good) or a Midtown OTB customer (bad). You decide. Fifth Avenue, NYC, July 2007.
Well, you already know how much I love Gregory Peck, and this candid shot of him with David Niven certainly doesn't disappoint. In fact, I can't find a bad picture of Gregory Peck. If you find one, please don't send it to me. On the set of "The Sea Wolves: The Last Charge of the Calcutta Light Horse" in India, 1980. (Getty Images; January, 1980.)
Ilie Nastase and Jimmy Connors in wide ties and fedoras. 1970. (Getty Images; January, 1970.)
