It's hard to figure out what to wear this time of year. One day you're in shorts thinking summer is here, and the next you're dramatically underdressed and running across the street to find some sunshine. Taking a cue from temperature-varying sports like skiing and hiking, the best solution to this problem is to dress in layers. Throw a light sweater on between your shirt and your blazer; add a scarf over your T-shirt and put a cardigan on over that; or, as one guy I saw did, wear a shirt and tie with a sweater over that, with a cardigan over that with a sweatshirt over that. I'm sure that sounds crazy, and I acknowledge that you would need an accomplished sense of proportion to pull that off, but trust me, he did.

Aside from matters of temperature, wearing layers can also be an opportunity to show more sides of yourself through your clothes. My favorite example of this is a photo of Richard Gere from 1980. Had he been wearing only the denim shirt and tweed blazer, he would have looked like your average prep school throwback. But with the addition of a pink zip-up sweatshirt, he looks sportier, younger, and less predictable. Wouldn't you love to give a first, second, and third impression all in one look?

It's hard to believe that this guy has four tops on and still looks good, but he does. Mott Street, NYC, January 2008.

Growing up, the only time I heard of William F. Buckley, Jr., was when I overheard people telling my stepfather how much he looked like him, and how they had the same "Long Island lockjaw" accent. It wasn't until I was older and read the newspaper regularly that I got my own sense of who William Buckley was. There's no doubt he was a talented writer and an influential political figure, as all the obituary writers celebrated when he died a few weeks ago, but what they failed to mention was how stunningly well dressed he was. Upon first glance you may just think, "Oh--classic preppy WASP," but actually his style was more nuanced and subtle than any simple classification would suggest. Yes he was preppy and classic and WASPy, but he had the knack for wearing one thing to give an outfit some personality (plaid shorts or a striped tie) without adding anything to distract from that (no monogrammed belt to match). Today many preppy guys I see in Palm Beach, Southampton, or Greenwich wear old school classic pieces as status symbols, like logos. They'll wear the Ray-Ban sunglasses with the Nantucket Red shorts with the yacht club belt with the polo shirt with the braided rope bracelet. Yikes! In my twenties I decided I really hated the preppy look for men--it had become about overstatement instead of understatement--but I realized recently that I just hate what it has become. If we could get the preppy look back to the elegant restraint of Bill Buckley I'd be proud to say I was a fan.

William F. Buckley, Jr., at home in Stamford, CT, August 1965. (Photo: Getty)

I do know men who can carry off wearing a fur coat. My stepfather, for instance, has a coyote parka that he wears at his house in the Adirondacks. I also have a more scruffy friend in his thirties who looks utterly convincing in a vintage beaver overcoat. But beyond that it's challenging for me to think of many cases where men pull off wearing an abundance of fur. However a bit of fur, most popularly a fur collar, is a different story. There are tons of options--a bomber jacket with a shearling collar, a down parka with a raccoon collar, or an overcoat with Persian lamb collar being among my favorites. And while an uptown man looks great wearing a fur-trimmed winter coat with a polished business look, I tend to think downtown guys look better if they dress down their fur with jeans and sneakers for a younger, more laid-back look.

This is a fantastic coat. I've never seen one like it. I like everything about it--the color, the fit, the combination of materials. Also, it's hard to pinpoint--it could be from the army-navy or from a very expensive designer. West 13th Street, NYC, January 2008.

As you've probably noticed, I have a thing for guys in military clothes, and bomber jackets are no exception. Maybe it's a holdover from a Top Gun obsession in my teenage years, or just that uniform thing I've talked about before. Regardless of whether you look like Tom Cruise--or not!--men look great in all incarnations of the bomber jacket--from the most authentic version worn by the Alaskan Air Force during World War II to edgy downtown reinterpretations created by forward-thinking designers. There are also lots of fabrics nowadays for grounded wingmen to choose from. While I am personally most partial to the teal nylon Army-Navy version with a fur collar, or the straight-out-of-the-war-photo shearling version, I do in fact like most kinds I've seen on the street and online, including Axl Rose's leather version (complete with Guns N' Roses logo) from the nineties.

I like this down puffer / bomber jacket combo - it's a sporty, but warm, look for winter. Noho, NY, January 2008.

Double-breasted coats and jackets don't have to look as country club formal as you might assume. Of course, if you choose to wear a navy blazer with brass buttons, you might have to work extra hard to add a playful dose of irony to its conventional aura--or maybe sometimes it's a relief to leave well enough alone. But in most cases, the traditional connotations can be overridden with new shapes, contrasting references, and a healthy sense of your own style. I often see my friend the designer Phillip Lim looking thoroughly modern in traditionally cut double-breasted blazers in fire engine red or cobalt blue, while Prince Harry boldly reinforces the old-school style of his double-breasted suit jackets by tossing a bowler hat into the mix. Perhaps most imaginative of all, though, is Andy Warhol, who threw a black leather motorcycle jacket over a classically cut black double-breasted blazer. But then again who was better than Andy Warhol at mixing references and identifying icons?

Phillip Lim, (pictured with Anna Wintour), looks entirely contemporary in his boxy blue double-breasted blazer. 3.1 Phillip Lim store opening, NYC, July 2007.

When it comes to jeans, for both men and women, I am a purist. The closer any pair comes to looking like a pair of Levi's 501s the better. I don't like any funky pocket details or weird colored stitching; and certainly any kind of contrived whiskering is out of the question. I am especially picky about the cut and fit, particularly for men. While there are always new trends in women's denim, I am most attracted to a traditional cut for men. Although you won't believe the number of men I see these days wearing jeans that are "skinnier" than most of my girlfriends would dare to wear. At first I found it confusing and odd--if skinny jeans were too trendy for me (and I'm often a sucker for trying out a trend), then how could so many guys be more adventuresome than a fashion chick like myself? But then I started to see the very rare guy whose skinny jeans really suited him. My favorite sighting was on a guy, must have been in his twenties, who had an otherwise laid back schoolboy look--Polo sweater (logo included), scruffy hair, and Docksiders--but his jeans were tapered. I would have passed him off as too predictable if his narrow jeans hadn't given me something to look at. I think they worked because they stuck out from the rest of his look. They were so unexpected. And doesn't every guy want to catch a girl off guard??

My favorite skinny-jeans wearer mixes a street trend with preppy classics. August 2007, Bedford Avenue, Brooklyn, NYC.

It's not a foregone conclusion that corduroy will make you look like a preppy schoolboy or a college professor. Of course if that is a look you aspire to, just throw on some wide-wale trousers and a cable-knit sweater and you'll be good to go. That look really does work for some men. But it's the less conventional sixties-and-seventies-vibe corduroy that captures my attention most. I've spotted guys on my block in vintage fine-wale Levi's corduroy pants, and, once upon a time, Steve McQueen in a strict corduroy blazer and Paul Newman looking the epitome of American style in various forms of corduroy -- they all revived my interest in this wintery staple. But its probably a 2002 picture of modernist architect Phillip Johnson -- the ultimate minimalist -- that took me the furthest away from the preppy connotations of corduroy. It always takes someone who is able to look at something for what it is, not for what it conjures, to truly reinvent a classic.

I have a very ambivalent relationship with Birkenstocks. While I would never wear them, I do occasionally like them on guys. They work especially well here to give a groovier look to his cord pants. Bleecker Street, NYC, September 2007.

When I look at pictures of men wearing scarves, I notice what a big impact they make on a guy's overall look. It's not really the actual scarf that makes me wanna take a picture of someone--in fact, I've never made a folder of scarf photos, which I often do when I find a recurring theme that I like. But then when I looked at all the recent photos that I do like, I noticed that most of the men were indeed wearing scarves. It seems that a scarf is this cozy, organic-shaped piece of cloth that adds a sense of the unexpected to an otherwise neatly tailored or put-together look. There's the navy scarf that reinforces the classic yet minimalist effect of one man's matching navy overcoat and wool cap. There's the brown tweedy-looking scarf that gives one guy's jeans and seemingly inexpensive overcoat a more together, grown-up feeling. And then there are the more colorful striped or patterned scarves that transform basic clothes into a statement of "I'm not Everyman. I have a way I like to look. And this is an easy way to express myself." An extreme version of a "statement scarf" was worn--successfully, in my opinion--by English photographer Norman Parkinson in 1970. It's a long length of leopard fur casually tossed over his shoulder, worn with a white sweater and white trousers. It's not a look that would suit many people, if any, but it certainly represents the enjoyable outer limit of how a scarf can make an impact.

I love this man's all-navy look. Madison Avenue, NYC, December 2007.

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)

If you look into the history of men's clothing, you'll see that so much of it originated as athletic gear. What we know as the polo shirt was actually invented in 1929 by Rene Lacoste as a tennis shirt. Even Gucci, from 1906 to 1938, was a leather saddlery shop that made high-end equestrian gear before it slowly diversified into a full service fashion house. Maybe men are most comfortable, when they've left the workplace, feeling close to the ball field even when they're not breaking a sweat.

Sometimes the competition-ready origins of these clothes are not so noticeable off the playing field. And on the other hand, clothes like sweatpants, tracksuit tops, tennis sweaters, baseball hats, and even snowboarding jackets have also made their way into the mix of acceptable streetwear. I see dads at my son's school every morning dropping off their kids in Converse All-Stars and their favorite European soccer team sweatshirts. I notice my husband wearing his cricket sweater both on and off the pitch when he's in England. And I even saw Ralph Lauren recently at a formal event wearing jodhpurs with a tuxedo jacket. While it worked on him, I may have to put a "Don't try this at home" label on that one.

Peter O'Toole, always the English gentleman, in a cricket cap. 1990. (credit: Corbis)

Bad boy Dennis Hopper looks unusually classic in his sport jacket layered over a rugby shirt. 1982. (credit: Corbis)

Count Carl von Bismarck exercises his royal entitlement to wear tennis clothes at the lunch table. 1982. (credit: Getty)

I love this guy's Bjorn Borg-inspired tennis shorts. I'm not sure New York City is the best place to wear them--maybe Venice, California or Miami? He looks great nonetheless. Bleecker Street, NYC, June 2007.

Millionaire playboy Gunther Sachs wearing a bobsled team jacket in Saint Moritz. Switzerland, 1970. (credit: Getty)

Two dads at my son's school reconcile early-morning drop-offs with easy-to-throw-on athletic basics such as a soccer sweatshirt and a loose Lacoste tennis shirt. Sullivan Street, NYC, October 2007.

Rod Stewart takes to the street in an Adidas soccer warm-up top. 1983. (credit: Getty)

My brother-in-law Charlie loves to play golf, and he collects shirts from the different courses he plays to wear in his everyday life. Because he's English, I think of him as gentleman jock. Dragon School family picnic, Oxford, England, July 2007.

While it's hard to imagine that Truman Capote actually played any sports, it's clear that he at least wanted to look the part. At home in Long Island, NY, 1965. (credit: Corbis)

This guy caught my interest for wearing basketball sneakers in the most unsportsman like way possible. He looks more like an English D.J. than a basketball player. Bleecker Street, NYC, September 2007.

Although we're used to seeing David Letterman in a double-breasted suit every night, I've heard he is actually a huge fan of sweats, as shown by the customized ones he's wearing here. 1984. (credit: Getty)

My husband, Christopher, hangs around our English cottage in his 20-year-old cricket sweater. Can you tell that he doesn't like having his photo taken? Oxfordshire, England, June 2007.

Bryan Ferry, making a departure from his tailored rock 'n' roll look, yet again confirming the old-school appeal of a cricket sweater. (Just to be clear, what started in England as the cricket sweater became, in America, the tennis sweater.) 1974. (credit: Getty)

I'm sure there will be a great divide on the success of Brad Pitt's look in this early photo of him. I think he looks super-hot, in a tacky eighties teenager sorta way. 1988. (credit: Getty)

Ralph Lauren (with wife Ricky) in jodhpurs and not a horse in sight. CFDA Fashion Fund awards, NYC, November 2007. (credit: Sherly Rabbani and Josephine Solimene)

I just can't help it. When I think about men wearing cardigans, Mr. Rogers pops up in my head, hanging up his sweater at the start of every show. It's a wholesome look, for sure, but that's all the good I can say about it. So needless to say it wasn't my idea to do a blog about cardigans. It was my assistant Chelsea's idea, and when the subject first came up, I'm sure I made a suspicious face. But because Chelsea's instincts are usually spot-on, I promised her I would keep cardigans on my mind while man-scouting.

I've now had a few months of cardigan observation, and I have seen enough guys doing it well to convince me that it's a look that absolutely works in today's context. A Fair-Isle sleeveless cardigan worn with a button-down shirt was toned down by rolled jeans and flip-flops; a shaved head seems to do wonders to counteract the inherent fifties "ideal husband" look; and, in one case, silver Vans (I know it sounds weird) worked to lessen the overt preppiness of a primary-colored striped cardigan.

It may have been Kurt Vonnegut who, once and for all, sealed the deal on cardigans for me. A picture I found of him in the seventies made it clear that the disheveled cardigan is by far the most masculine cardigan. And while it is possible to look good in a tidy, buttoned-up cardigan--as British jockey Billy Cook did in the late forties--it does require you to keep Mr. Rogers out of your neighborhood.

   I like how casual and not overly considered Kurt Vonnegut looks in his clothes. I don't know what he wore all the other days of his life, but this would have made for a good daily uniform. There's something very attractive about men who know themselves well enough to figure out what suits them and stick with it. 1970s. (credit: Getty Images)

Just from looking at his athletic build and shaved head, I would have never suspected this guy would be a cardigan wearer. He looks great though. Mercer Street, NYC, October 2007.

I LOVE the sweater-as-jacket idea that this 1950s school boy has adopted. (credit: Getty Images)

A friend sent me this picture. It took me a moment to see why this guy's look was remarkable. Then I realized that his tux jacket was actually a knit cardigan. I've never seen this before. I'm really into it. Ludwig Heissmeyer at the Metropolitan Museum of Art, November 2007.

David Hockney shows a more artsy side of the cardigan look in his studio. 1978. (credit: Getty Images)

I can't quite figure out what this guy was trying to accomplish with his hairstyle, but I like his outfit a lot. Spring Street, NYC, October 2007.

Legendary Penn football coach and Heisman trophy namesake John Heisman shows us the masculine extreme of the cardigan spectrum. 1920. (credit: Corbis)

This guy clearly has his own think going on--prepster on top and hipster on bottom. I can get with it. Broadway and Prince Street, NYC, June 2007.

I love this guy. It's Ian Gillian, lead singer of a band called Deep Purple. I've never heard of him or his band, but his layered sweaters with the contrasting long hair and classic watch look particularly good. 1971. (credit: Corbis)

Famed Art Historian Meyer Schapiro stands for his portrait in a more academic layered-sweater look in 1981. (credit: Getty Images)

While I wouldn't necessarily recommend wearing a wool fisherman's cardigan with nothing underneath, Elliot Gould (shown at his opening of Drat! The Cat! with his then-wife, Barbra Streisand) stands out from all the other pictures of men in cardigans--so I felt he deserved some attention. 1965. (credit: Corbis)

My editor, Ned Martel, is a confirmed cardigan enthusiast--although I didn't know that until recently because I rarely see him in his office. So I made the trip to catch him in action. The Conde Nast building, Times Square, NYC, November 2007.

Prince Philip leads his carriage team back to their paddock at Windsor Castle after the Royal Windsor Horse Show. His look is about as old-school English as you can get. 1973. (credit: Corbis)

Thomas Ince, the silent film director and producer who died mysteriously onboard the yacht of William Randolph Hearst, shows that the cardigan-as-jacket idea goes way back. 1918. (credit: Getty Images)

This guy's look is somewhere between Chariots of Fire and a Prada store salesman. I hope it reads as more the former than the latter. Prince Street, NYC, July 2007.

Legendary Blues musician Little Walter defines sixties cool. Its the soul version of classic menswear. Theresa's Lounge, Chicago, IL, early sixties. (credit: Getty Images)

This guy was better in person. He must have been frightened by having his picture taken because he looked great walking down the street. I hope his modern take on preppy comes across. Lafayette Street, NYC, August 2007.

You must know by now that I love Bing Crosby's cool cat style. Seeing him in a cardigan AND standing next to David Bowie hits it out of the park for me. 1977. (credit: Getty Images)

Australian jockey Billy Cook (in a sporty fully buttoned-up cardigan) with trainer Walter Nightingall watch an exercise session at Epsom Race Track, England, 1949. (credit: Corbis)

There's one thing that might finally topple the so-called rules of seasonal dressing: global warming. I'm already beginning to notice the absurdity of men feeling like they can't wear white or linen or shorts after Labor Day when it's 80 degrees out in late October. And while the dictators of convention may not be ready to make an official change in the etiquette book, I like the idea of men prolonging summer in their wardrobe (or maybe getting an early start on spring?) by wearing unseasonably bright colors.

A lavender sweater, for example, has a different feeling when worn in June than it does in October. The common perception is that if you're wearing bright colors in warm weather, then you are joining the masses, becoming part of the norm. It seems like a bigger commitment, however, to wear, say, red pants on Madison Avenue after Labor Day. Did someone say dandy? I hesitate to label it that way because--while there's nothing wrong with being a dandy if that suits your style--there is a way to be colorful in the later months of the year without feeling like a peacock.

The most obvious way to wear color off-season is to add just a hint of it--an emerald-green pocket square, a duck-egg-blue tie, or if you're a free-spirited artist like David Hockney, even two different colored shoes! The men who wear full-on jolts of color--a tangerine sweater or a fire-engine-red military coat--look best when the rest of their outfit is toned down and neutral. Mind you, there is the rare exception, like the sixties image of English photographer Patrick Lichfield looking confident and enviable in a purple shirt with canary-yellow pinstripe pants. But take on looks like that with caution--even if you're dressing for springtime at Thanksgiving, you still don't want to look like an Easter egg.

The shopkeeper at Richard James in London (my favorite men's store) knows how to wear intense color to his advantage. Savile Row, June 2007.

I love seventies pictures of the British royal family--obviously the Windsors were never trendy, but a laid-back vibe seems to have seeped in. Note the longer hair and the orange sweater. 1978. (Getty Images)

My friend Carlos Mota, in color coordination with my daughter Coco's riding chaps. Oxfordshire, England, 2007.

Charles Dana, the founder of the Lyford Cay Club in the Bahamas, in a preppy linen blazer. 1983. (Getty Images)

This Ralph Lauren employee would look pretty run-of-the-mill without that pop of emerald. East Fifty-ninth Street, NYC, October 2007.

British one-hit wonder Whistling Jack Smith wears a recycled bright red military jacket. The cloudy fall weather makes a good backdrop for the intense color. 1967. (Getty Images)

Before he brought the world Cosby sweaters, Bill Cosby fought the winter gloom with a yellow turtleneck. 1966  (Getty Images)

Have you noticed that I have a thing for dark-skinned guys wearing bright colors? On a white guy this outfit would be too preppy for my tastes, but this guy's interpretation of color, proportion and attitude makes me a fan of the whole package. Madison Avenue, NYC, October 2007.

This guy does a whole other thing with red pants--to equally strong effect. Williamsburg, Brooklyn, June 2007.

British-born painter David Hockney in his trademark mismatched shoes. The guy behind him in red pants looks great too. 1980. (Getty Images)

This guy has a good combination going on--the colors are bright but they're not screaming at me. Also, I've been noticing men wearing their ties shorter and shorter recently. What's that about? I'm not complaining. Spring Street, NY, October 2007.

The amazingly stylish sixties and seventies supermodel Twiggy is followed here by her equally stylish manager and then-boyfriend Justin De Villeneuve. He manages to suggest a Nantucket tradition in a laid-back, not-taking-it-so-seriously way. 1970. (Getty Images)

Sometimes wearing a less obvious color, like the tangerine linen shirt my stepfather, Will, is wearing here, works to great effect. Wainscott, NY, October 2007.

I'm not suggesting that you make like James Brown and wear a pink shiny cape--but I do like the example of how great adding a flash of color can be. 1969. (Getty Images)

 I would never have thought this guy's look was remarkable without the green pocket square. Broadway, NY, October 2007.

Douglas Fairbanks, Jr., looking great in not one but two loud colors. It helps that the blue shirt matches his eyes. 1967. (Getty Images)

I have to admit to you that this guy had knee socks on below his cut-off green shorts. I'm just pretending I didn't see them because this part of him looks great. Brooklyn, NY, October 2007.

If I momentarily suspend my attraction to Neil Armstrong's good looks and awesome feats, I notice how much I like the simplicity of his red cap.  Houston, Texas 1969. (Getty Images)

British society photographer Patrick Lichfield looks contemporary in this picture. I would never have thought a man could pull off a lavender shirt with yellow pants. But he does. That's the amazing thing about having your own style--when you believe in it you can do things that no one else can.  Port Ercole, 1968.  (Getty Images)

I've been surrounded by plaid in some form or other throughout my life, but my teenage years at a New England boarding school and summers spent in the Adirondacks stand out the most. L.L. Bean Stewart plaid flannel shirts, Lands' End black watch plaid pajamas, and J. Crew barn jackets lined with Kerr tartan wool all contributed to the idea that plaid was the trademark of a sporty, preppy life. So when I went to college at Brown and moved--geographically and aesthetically--away from that lifestyle, my taste for plaid got left behind. I was more attracted to the Euro dude driving a brand new Beemer than the Connecticut WASP in his messy flannel driving his mother's old station wagon seeming all too familiar.

After a long hiatus, I'm not sure if it was seeing a late-seventies picture of Bruce Springsteen looking very sexy and totally rock 'n' roll in a plaid button-down shirt or if it was the decidedly not preppy guys in my Lower East Side neighborhood who have decided to bring plaid back in a personal, less obvious way that has gotten me excited about it again.

What I'm seeing now is that same old plaid flannel shirt worn with a more rugged lumberjack-style beard, or a subtle plaid lining in a vintage motorcycle jacket. It is in these interpretations that plaid has taken on a new meaning and made me realize, as with everything else, that it's all about the context. And maybe I've gotten older and wiser and more secure, because I'm starting to find those sporty, preppy guys pretty cute again too.

My childhood friend Sam Byram fishing in a Royal Stewart plaid flannel. Long Island Sound, NY, 1994.

You might think plaid causes things to clash, but in Bing Crosby's case his jacket pulls the rest of his look together. London, 1961.  (credit: Gettty Images)

This is my second-favorite vintage photo of Bruce Springsteen. I love the plaid in pink(!) and black. You'll see my absolute favorite one of him in an upcoming blog. 1978. (credit: Corbis)