In the 20th century, the jewelry that men wore seemed to change dramatically from decade to decade. Early on, such adornments seemed mostly contained (at least in first-world cultures) to discreet symbols of wealth and privilege--watch fobs, cufflinks, tuxedo studs--all worn in traditional contexts. The '50s then saw men experiment with ID bracelets and chains on their wallets; the '60s brought St. Christopher medallions out in force; it seems that the bigger and shinier the better was the attitude in the '70s (check out Fernand Legros in the matching large gold necklace and matching belt); and the '80s and '90s got us ready, with hip-hop chains and diamond studs, for the 21st-century focus on bling.

In this new century, therefore, anything goes. Today's spectrum ranges from dads wearing colorful, plastic bracelets lovingly made by their children to Britain's Prince Philip looking almost like a tribal warlord given the amount of medals he wears to a formal occasion. It seems to me that although jewelry will always be some kind of display of wealth and status, it is also a way to add some personal customization in an increasingly global world. And while I welcome rebels to run in all circles, just try to avoid using Jack Sparrow as your muse.

Paul Newman getting into the '50s feeling with his greaser haircut and a silver ID bracelet. 1956. (Credit: Getty)

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)

I don't own a raincoat for two reasons: First of all, I usually make due with the biggest umbrella I can find, and secondly, there are several dozen options in my husband Christopher's closet that are just better than anything made for women. It's mostly on the weekends when I feel free to grab one of my husband's 17 raincoats, and I know he likes how I look in his loose red Patagonia slicker. He has all these options because, frankly, he can't be bothered with umbrellas and, even if he could be, he'd lose one the first place he put it down. Furthermore, he rides his mountain bike around the city no matter the weather and keeps himself fully covered--he even has rain pants and rain hats!

Christopher's raingear is on the casual end of the spectrum, whether it be military-inspired or just a plain and simple slicker. But in my travels uptown, I kept checking out business men who want to, have to, aspire to look put-together when they go to work. I sympathize entirely: They can't throw a standard-issue anorak over a custom-tailored suit, so they opt for classic shapes--double-breasted trench coats, James Bond–style overcoats--but in technologically updated waterproof fabrics. Nothing seemed overly designed or too tech-y, everything was formal and functional. Now if I could just find one in my size.

When I think of men's raincoats this is the kind of coat that pops up first in my head. I'll bet it was made by London Fog. 1986. (Credit: Getty)

This guy's coat is the here-and-now version of Reagan's classic overcoat. You can't get more basic--in a good way--than this. Lower Fifth Avenue, NY, September 2007.

Was Edward R. Murrow born in this look? I feel like he's wearing the same thing in every picture I see of him. Clearly it worked for him, wherever he went. In this instance, he was in England to cover WWII for CBS Radio network. London, 1941. (Credit: Getty)

Does anyone know who this guy is? He looks so familiar to me. I feel like he runs an art museum or something. Nevertheless he has a great sense of style and proportion. Also did you clock the uptown beard? Madison Avenue and 61st Street, NY, October 2007.

American business man Harold Vanderbilt standing in the rain with his wife. My heart rate speeds up when I look at this picture. It's that good for me. 1935. (Credit: Getty)

A technical version of a trench. Very James Bond. Park Avenue, NY, October 2007.

Captain Mark Phillips, Olympic gold medal-winning horseman and former husband of Princess Anne of Britain, wears a traditional English sporting raincoat. You should know by now that I'm a sucker for any '70s photo of the British Royal family. 1978. (Credit: Corbis)

My husband Christopher, in a matching rain slicker and hat, walks our daughter Coco around the sequence of jumps at a horse show in England. She came in third. Heythrop Pony Club, Moreton-in-the-Marsh, England, June 2007.

Although I like the look of this coat, I would say it's good for drizzle at best. Union Square, NY, September 2007.

I can't tell you how many pictures I found of men who, like me, walk around in the pouring rain with an umbrella, but no waterproof coat. Stan Smith, Wimbledon, 1972.(Credit: Corbis)

I love the idea of a trench "jacket." Madison Avenue, NY, October 2007.

Eric Shipton, a Sri Lanka–born British mountain climber and explorer, stands with a Chilean glaciologist in their all-weather gear. Eric Shipton is hot--the fact that he's an explorer, his clothes, the way he's standing--it all works for me. Tiera del Fuego, Chile, 1962. (Credit: Getty)

This blog wouldn't be mine without a groovy Brooklyn dude thrown into the mix; and his military-inspired raincoat with the double-breasted "lip" is fantastic. Bedford Avenue, Brooklyn, September 2007.

This is what I call a dressed up casual look. He's wearing jeans, there's no tie; but the overall look is very pulled-together, raincoat and all. East 59th Street, NY, October 2007.

I can't really tell what these Haitian men are wearing. Are the coats always so shiny? Or are they just wet? Did the guy on the left drape a detached hood over his head? All I can tell you is that I really like the overall effect. 1974. (Credit: Getty)

I love a poncho--and I'm sure you know this but you have to be pretty tall to carry one off. Woodstock, 1969. (Credit: Corbis)

Some more contemporary poncho-wearers in Beijing rush hour traffic. Do you think purple is a standard-issue poncho color in China? I hope so. 1993. (Credit: Getty)

Sugar Ray Robinson stands outside Madison Square Garden during a rain delay of his match against Joey Maxim. Maxim defeated Robinson for the light heavyweight championship two days later. 1952. (Credit: Getty)