I've always been a sucker for a show of originality in a man's outfit. Whether it be a thoroughly modern young fellow rockin' an aristocratic bow tie, Sammy Davis Jr. throwing a cape over his tuxedo, or Le Corbusier--the man himself--wearing his quirky round black frames so convincingly that they became his signature, these flashes of distinction unfailingly show me a man's inner confidence. You might assume that men who have their own style spend more time than others getting dressed, but most snappy dressers I know are men who are unafraid of what others think and walk the line between standing out and not looking like a freak with relative nonchalance. It's not the time spent in your closet putting together the day's get-up that counts toward showing personality. It's the more important, bigger-picture endeavor of knowing who you are and how you want to present yourself to the world. Simply said, these men are not scared to experiment.

One of the things I love most about spending a month in England each year is witnessing the relative freedom English men have in getting dressed, as compared to most American men. Having spent my eleventh consecutive summer there this year, I am now accustomed to men--fathers, husbands, bachelors--in brightly colored floral shirts, velvet jackets worn with sneakers, large family crests emblazoned on sport jacket pockets, and three-piece tweed suits. I suspect it is because these men are so intimately acquainted with tradition that they can so freely break from it. That said, by far the most impressive exhibit of eccentricity came walking at me down the street not far from my lower Manhattan home just a few weeks ago. He was an African American guy dressed traditionally in a humble yet well-tailored brown corduroy jacket and grey flannel trousers. But he had on scuffed wing tips, the collar on his jacket was standing up, his fedora was casually tipped to one side, and there was a pink handkerchief tucked into his breast pocket. What made my jaw drop was that he didn't look like he was trying to hard, he just knew who he was. I think the English would have been impressed.

If I had to nominate a man I saw on the street for best dressed of the year, this guy would win hands down. He has great style but looks entirely at home in his clothes. LaGuardia Place, NYC, September 2007.

If you're familiar with Tom Wolfe's dandy style, you might agree with me that he overdoes it sometimes. But here he has just the right amount of groove (his three-piece suit) and polish (his matching tie and pocket square). 1966. (Credit: Getty)

Wes Anderson has a very strong sense of aesthetic identity--in his movies and in his clothes. He often takes risks (a velvet bow tie can make you look like a clown if you tie it too neatly), but always within the boundaries of his confirmed old-school preppy gentleman style. Venice Film Festival, 2007. (Credit: Corbis)

I love how, throughout their history, the Stones have taken iconic pieces of gentlemen's clothing (boater hat, bow tie, schoolboy jacket) and mixed them into their otherwise rock 'n' roll wardrobe. Paris, 1970. (Credit: Getty)

You can't beat dreads and neatly tailored tweed as a combination. Madison Avenue, NYC, October 2007.

General George Marshall's mix of the formality of a bow tie with the informality of shorts and slippers is original and revealing. Fire Island, N.Y., 1939. (Credit: Getty)

When I think of an Englishman in a velvet jacket, I can't help but think of the silk ascot and monogrammed slippers that might go with it. Not for this guy--the grungy hair and worn-in sneakers make him stand out--especially on Savile Row! London, June 2007.

I made the mistake of asking my sister if she liked this picture of Le Corbusier in the "Philip Johnson" glasses. She said. "Do you mean the picture of Le Corbusier in the 'Le Corbusier' glasses?!?" Here he is--looking dapper in a three-piece tweed suit, bow tie, and the glasses he made famous. 1944. (Credit: Getty)

I love how this guy (obviously a Ralph Lauren employee) mixed a conventional tweed jacket and striped tie with ironically casual jeans and a bandana pocket square. Madison Avenue, NY, October 2007.

Most men would likely choose between the large polka-dot tie and silk handkerchief (if he were even to wear either), but Yves Saint Laurent boldly wore both. 1972. (Credit: Getty)

This guy made me laugh--in a good way. He walks the line between classic cuts and a seventies disco vibe with great results. I'm not sure he'll appeal to everyone, but I like him. East Sixtieth Street, NYC, October 2007.

Wearing a morning suit and a top hat to work as a garbage man (or "dustmen" as the British refer to them then) brings the height of white collar style to a blue collar job. Hounslow, London, 1958. (Credit: Getty)

I was compelled to include Wes again, in this carefully curated casual look. Even though I believe he's a true original, if there was one man in this blog that I suspect may take a while to get dressed, it would be him. Berlin [CK] Film Festival, 2005. (Credit: Corbis)

I've mentioned before that I usually avoid using film stills as examples of personal style, because I can't help but assume that the clothes of a given character are more about the fictional portrayal than the man inside them. But in rare cases--such as this picture of Jason Robards in The Iceman Cometh--I can't resist. I'm impressed by how masculine he looks, despite being decked out in accessories--the watch fob, the flower in his lapel, the boater hat. Regardless of whether the credit goes to the costume designer for creating the look or to Jason Robards for completing it--it's completely great. 1960. (Credit: Getty)

Being a stickler for authenticity, my husband, Christopher, would only ever dare to wear these highly stylized grouse-shooting clothes--sock pompoms and all--on the moors of Scotland. I sometimes wish we lived in Scotland so I could see him dressed like this everyday. Cawdor Castle (of Macbeth fame), Scotland, August 2002.

Sammy Davis Jr. wearing the aforementioned cape over his tuxedo. 1971. (Credit: Getty)

Christian Louboutin's otherwise straightforward outfit is a given a breath of new life by the exotic crest on his breast pocket. Gramercy Park Hotel, NYC, September, 2007.

The Impressions, a seventies doo-wop/gospel/soul band, doing their best to look slick. 1977. (Credit: Getty)