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.

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)

The way I see it, nobody expects to see a man walking down the street holding anything other than a briefcase or maybe some piece of luggage.  There just isn't an accepted norm of what kind of bag a man is supposed to have. I know they have lots to haul around--iPods, newspapers, umbrellas, gym clothes, and God knows what else--yet we don't even have a name for the various lugging devices men make do with. I've heard all sorts of terms that don't seem quite right: man bag, satchel bag, and worst of all, murse.

I've noticed that men adopt mysterious rules to keep themselves far from the female leagues of purse-toters. My husband carries a black nylon tote with red straps and only ever in his hand, never over his shoulder--not exactly sure what that's about. I like how messenger bags look, with their cross-body strap, and when they're made out of leather, they look more grown-up than the original canvas or nylon--and one step away from the gritty bicycling tribe that popularized them. And sometimes I see bags men lug back and forth from the gym that are so big that it seems like a whole locker was dumped in there--these should look like gym bags, not body bags.

The newest thing I've noticed is men using bags to express an interest, an image, or a hobby. A vintage Lonsdale boxing bag made one guy look rugged no matter what else he had on, and I liked when I spotted someone with a small canvas bag with the logo of a cool gallery or out-of-the-way bookstore. Even a canvas shoulder bag with big stripes can turn a guy in a classic button-down and plain-front trousers into someone worth knowing.

 

When I asked my husband if he liked this picture of Bjorn Borg with his tennis bag, he said, "What's not to like about Bjorn Borg?" 1979 (Getty Images).

 

This is actually my favorite bag I've seen on the street. It's classic, it's functional, and I've never seen one like it before. Madison Avenue, NYC, July 2007.

 

British Heavyweight boxing champ Henry Cooper, with an old-fashioned gym bag, 1970 (Getty Images).

 

Sometimes it's cool to carry something that just works and is easy to carry, like this highly functional backpack. Bleecker Street, NYC, September 2007.

 

Prince Carl Gustaf XVI of Sweden on his way to school with his buddies. All of these bags are great. 1957 (Corbis).

 

French novelist Pascal Bruckner in his library with a good-looking and functional carry-all. I was really excited when I found this photo on the Internet--I love discovering people this way. 1983.

 

This guy is going for a more casual banker look (or I assume so: His bag said Morgan Stanley all over the trim). I just can't tell if his too-short pants are intentional or not. The bag definitely works though. Bleecker Street, September 2007.

 

London D.J. Johnnie Walker with a leather "doctor's bag." 1967 (Getty Images).

 

This guy was a cool cat. It's clever the way his overall look makes his L.L. Bean canvas tote seem NOT preppy, despite the monogram. Bleecker Street, NYC, September 2007.

 

The Twilight Zone writer and TV host Ron Serling with his family. By now, the TWA bag is a confirmed classic. 1962.

 

I love the design of this Filson bag but can't help but think of its original function, which was to carry home dead fish. To me, these bags look better in the country than in the city. Brooklyn, NY, September 2007.

 

A paper boy in England. Love the bag. 1959 (Getty Images).

 

A writer with a "message" bag. As it advertises a contemporary art space, I guess it tells us that he is up on his culture. Boerum Hill, Brooklyn. September 2007.

 

When Mick Jagger isn't busy being an over-the-top rock star he actually has great taste, as evidenced here by this very classic (probably old Gucci) carry-on bag. 1972 (Getty Images).

 

Highly celebrated war photographer Don McCullin on assignment with a nylon shoulder bag in the Philippines. 1986 (Getty Images).

 

When you are as glamorous as Egon Von Furstenberg was in the seventies (pictured here with then-wife, Diane), you can get away with carrying around your stuff in a brown paper bag. (Getty Images)

 

Somehow flip-flops have become an acceptable form of "mandal" for steamy weather, but I still know a large number of men who just won't go for open-toed shoes. What options does that leave for boating trips, beach excursions or even just walking around the city? Well, there are espadrilles, the canvas slip-ons with braided straw soles, and I know they might draw equal opposition. But hear me out, especially if you're an old-world kinda guy. I spent three summers of my late childhood in France, where espadrilles are what everyone—men and women—wear all summer, and I have vivid memories of my stepfather's well-worn version in navy blue. His clothes are always clean-cut, no-nonsense and accompanied by the coolest inherited accoutrements (a Breguet pocketwatch, diamond Cartier studs and countless engraved cufflinks are among his high-end hand-me-downs) and espadrilles fit right in with his style.

I had my doubts that I'd find any men at all wearing them on the streets of New York, but happily I came across quite a few, albeit in updated incarnations.  I saw canvas slip-ons, sans the braided sole, as well as Tom's shoes, whose proceeds help children-in-need get their own pair of Tom's. One breezy discovery was a crochet version of a slip-on, but you probably have to see them (below) to believe that they actually looked good.

At the other end of the summer shoe spectrum is what I have always called Top-Siders, or, as others may deem "boat shoes." In classic form-follows-function spirit, Paul Sperry designed Top-Siders in 1935 to keep you upright on the deck of a boat. Their boat-y relevance peaked in 1939, when the US Navy contracted Sperry to outfit thousands of sailors. And then in the sixties they resurfaced in abundance on college campuses. When I was Creative Director of Hogan, an Italian leather goods company, I was determined to re-invent the boat shoe and bring them back in fashion. The trouble was, they didn't need reinventing. So I just had to wait until the original makers like Sperry and Quoddy Trail in Maine realized what a classic they had and brought them back again. That moment has arrived.

A Slim Aarons portrait of 70's TV actor (and old money Philadelphia WASP) Samuel Chew Jr. in red espadrilles. 1975. (credit: Getty Images)

 

This guy's espadrilles came from Germany. He apologized for the socks, quite rightly so. Madison Avenue, NYC, August 2007.

 

JFK with his sisters in 1939. He's really going for it with the ankle straps.

 

My friend Kate Schelter sent me this photo of herself with Tom's founder Blake Mycoskie wearing their Tom's in Istanbul in July.

My stepfather, Will Stewart, on one of our many summer trips to France in the 80's.

A reluctant subject on his way to the gym. Before he ran away he dropped the name of a friend of mine at Vogue who told me that he is Diego Garcia, the lead singer of downtown rock band Elefant. Spring Street, NYC August 2007.

James Mason, reading a script on the set of Julius Ceasar. 1952. (credit: Time & Life Pictures/Getty Images)

These are the crochet slip-ons I was talking about above. Apparently they came from a Polish men's shoe shop in Brooklyn. I really like them. Bedford Avenue, Williamsburg, Brooklyn, August 2007.

Sam Buffa. Again. He happens to live AND work on my block, and he's got great style. He's wearing boat shoes from Quoddy trailshoes, a family owned, handmade shoes company in Maine. Freeman Alley, NYC, August 2007.

Ezzard Charles, heavyweight boxing champion of the world. 1950. (credit: Time & Life Pictures/Getty Images)

I've been noticing top-siders in new and different colors, like white. Williamsburg, Brooklyn, July 2007.

Famed Interior Decorator Albert Hadley in original Sperry Top-Siders. 1991. (credit: Getty Images)

When Ned Martel (my editor at Men's Vogue) heard I was including topsiders in my blog he showed up to lunch proudly wearing these black ones. I also noticed that he was wearing wayfarers and a white seersucker shirt too. At least somebody is listening to me. Bryant Park, NYC, August 2007.

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.)

In case you couldn't tell from my previous blogs, I have an obsessive habit of looking through vintage photos online. For me there's no greater thrill than looking through 67 pages of, say, run-of the-mill men in tuxedos when something out of the ordinary stops me -- jeweled studs! -- and speaks volumes about personal style.

So the other day I was walking on Madison Avenue, looking out for men who catch my eye, and I noticed in retrospect that I didn't clock any men wearing ties. I do like men in ties -- a lot -- but I wasn't really feeling it from the men I saw that day. So when I got home I went looking for inspiration online and did a men-in-ties search from 1940 to 1985. Looking through my selections, I was far more interested in the men who clearly wore ties by choice, as opposed to obligation or convention. Musicians like Bryan Ferry and Mick Jones, screen legend Michael Caine, sixties photographer David Bailey -- they all wore uncompulsory ties to great effect. These men had no real reason to be wearing a tie other than choice, and this choice alone brought something different and more personal to their look. A tie worn under a sweater, or with no jacket and rolled-up shirt sleeves, or even just a tie with a loose knot, all looked exciting to me.

Conversely, I also feel something for a guy who is a proper, devout tie wearer and wears one regardless of his location or situation. Coming out of my apartment the other evening, I saw a very attractive and elegantly dressed older man standing outside The Box, a scandalous dinner theater on my block that is more known for local Lower East Side hipsters than Upper East Side patriarchs. I asked a friend and learned that he was Lewis Lapham, former longtime editor of Harper's magazine. Even though his tie-wearing surely stemmed from convention, he certainly didn't need to be wearing one on Chrystie Street, no matter the occasion. Lewis Lapham is a rare bird, and hopefully not a dying breed.

 

I didn't get the chance to ask this guy where he was going but, judging from where this photo was taken (just outside the Ralph Lauren offices), I'd be willing to bet that he works there. He looks the part entirely -- to great effect, mind you. Madison Avenue, NYC, July 2007.

Filmmaker Wes Anderson looking rather underdressed in a tie at a film premiere in 2003.  (Getty Images, March 6, 2003.)

This picture from the eighties of Bryan Ferry's casually-worn tie gave me the idea for this blog.  (Lynn Goldsmith/Corbis, 1980s.)

A tie with jeans and sneakers can be scary, but this guy pulls it off by keeping it simple and clean. SoHo, NYC, July 2007.

Topper Headon of the Clash helped the uncompulsary tie become an iconic rock star look. 1980s.  (Getty Images, January 1, 1980.)

The American rock band, The Byrds, 1970. (Getty Images, January 1, 1968.)

A friend, set designer Sebastien Sergeant,who lives across the street from me. Forsythe Street, NYC, May 2007.

A white shirt and black tie and oversized sunglasses became legendary actor Michael Caine's signature sixties look.  (Getty Images, May 14, 1965.)

I love the Army jacket over the shirt and tie. The Automat, London, June 2007.

English fashion photographer David Bailey, 1967.  (Getty Images, May 14, 1965.)

Lewis Laphan outside The Box. Chrystie Street, NYC, June 2007.

I can't remember a time when Ray-Ban sunglasses have been out of style. Sure, their popularity comes and goes, but unlike Vuarnets, "goggle" glasses with blinders, and Oakley shields, Ray-Bans always look classic. In fact it's precisely the old-school shape of both the Aviators and Wayfarer styles that makes the look of forties aviation pilots, sixties movie actors, seventies rock stars, and eighties brat-packers still look relevant today.

Because we've seen Ray-Bans worn in such a high profile way for so long, I'm now most impressed by guys who have found new interpretations of the Ray-Ban look. I saw a guy on the street the other day whose sunglasses looked liked classic aviators in every way except the edge of the frames was shaped differently. I asked him if they were Ray-Ban, and he proudly declared they were "street" glasses he bought in Dakar. I also recently noticed a street vendor selling aviators in updated shades of electric blue, white, and bottle-green. You see, the logo really doesn't matter. The idea is basic and repeatable, the very definition of a standard. It's just a little American configuration of glass and metal (or glass and plastic, as the case may be) that has taught a world of men how to go incognito.

I almost didn't recognize Lou Reed looking so clean cut. If it wasn't for the headphones, he'd almost look preppy! 1981. (Photo: Corbis)

General Douglas MacArthur in original Ray-Bans during World War II, 1944. Ray-Ban Aviators were invented (in 1939) to reduce glare for fighter pilots. (Photo: Corbis.)

This guy bought his Ray-Ban-esque glasses from a street vendor in Dakar. Chrystie Street, NYC, 2007.

If you ever doubted that Clint Eastwood was one of the coolest guys of all time, I hope this picture will change your mind. 1956. (Photo: Getty Images.)

I love how this guy makes preppy look newer and sleeker, Wayfarers and all. Bleecker Street, NYC, 2007.

Jazz pianist George Shearing, 1958. (Photo: Corbis.)

Wayfarers, Vans, and a Strand Bookstore bag -- he knows what he's doing. Broadway, NYC, 2007.

Bleecker Street, NYC, 2007.

Black Aviators must have been the Ray-Ban of choice for seventies rockers (Peter Wolf from the J.Geils Band wore them, too). Mick Jagger, Paris, 1979. (Photo: Getty Images.)

A musician in Washington Square Park, NYC, circa 1955. (Photo: Getty Images.)