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)

This guy's doing his own street-style impression of plaid--hooded sweatshirt and all. It's rare that I like a shirt buttoned up all the way, but it works for me here. Union Square, NY, October 2007.

Controversial Brit artist Damien Hirst in a seemingly rare quiet moment. I like the larger-scale plaid. 1996. (credit: Getty Images)

Here's another street shot that Ned Martel, my MV editor, took in Copenhagen. The blue-and-black plaid looks excellent and you gotta love the bike basket filled with empties. The jeans tucked into the yellow socks would give me pause, except that bikers have to do that to keep their jeans out of the gears. August, 2007.

James Bond creator Ian Fleming looking distinguished in a plaid shirt. 1951.  (credit: Cecil Beaton/Conde Nast Archive)

This guy's new-wave, pastel-plaid look was captured on Bedford Ave. in Williamsburg, but my editor recognized him as the shopkeeper of UNIS, a great menswear store in lower Manhattan. Brooklyn, NY, September 2007.

The Sex Pistols' Johnny Rotten gave plaid a permanent home in punk iconography with his ironic use of the Scottish staple. 1978.  (credit: Corbis)

A typical downtowner wearing a rugged beard to make his plaid shirt more lumberjack than prep school boy. Howard Street, NYC, October 2007.

David Bowie, at home, looking effortlessly cool in a highly stylized look. My husband spent most of his teenage years in England desperately trying to look like David Bowie (eyeliner and all). So this one's for him. 1976. (credit: Corbis)

John Seeger, at my summer house in the Adirondacks, living out his salad days in Dress Gordon plaid. St. Huberts, NY, 1993.

Joseph Heller, writer of literary classic Catch 22, takes the prize for his plaid look. I'm most impressed by his ability to wrap a sweater around his shoulders (the horror!) and still look thoroughly rugged, not to mention hot!  (credit: Conde Nast Archive)

A plaid detail is a good thing. 42nd Street, NY, May 2007.

The Duke of Windsor, who was always up for the regal look if not the responsibility, in a full tattersall tweed suit. I'm not saying every man could pull this off, but he certainly does. 1967. (credit: Conde Nast Archive)

This picture comes with instructions: Take three fingers and place them over the highly questionable "murse" this man is carrying. Then you can appreciate the dapper plaid suit he is wearing. I wouldn't imagine that a plaid suit would have a home on the streets of New York City, but in this case it absolutely does. Madison Avenue, NY, October 2007.

My teenage crush Billy Boardman kicking back with a G&T on a camping trip. Upper Ausable Lake, NY, 1995.

From the neck down, Andy Warhol looks like he walked right out of my neighborhood. Whether or not they'd admit it, Warhol seems to be the one who Lower East Side hipsters are channeling today. 1981.  (credit: Getty Images)

I have a weakness for men in military clothes, and I'm not alone. I'm not sure if it's the clichéd "uniform" aspect of, say, army shirts and bomber jackets (I also can't keep my eyes off men in firefighting outfits); or maybe I like the offbeat, counterculture feeling of men buying them from less expected places like the Army-Navy store or an out-of-the-way vintage shop. Regardless, I guarantee that if you're wearing some kind of military-inspired clothing (the more original the better), a watchful woman will give you a proper once-over.

I couldn't find any pictures of men before the 1960s wearing war-inspired looks, unless they were actual soldiers--this must have had something to do with Vietnam. And while inspiration can be taken from the more official wearers, like former Chinese president Chiang Kai Shek, a forties British Royal Air Force pilot, or even Elvis Presley during his induction into the Army, it was actually peace advocates--John Lennon most iconically--who popularized the military look as an acceptable form of streetwear.

These days Army, Navy, and Air Force looks seem to be more popular than ever--Vietnam redux? The span runs from the most expected (but still great-looking) khaki-green multi-pocketed shirt or jacket to Freemans Sporting Club's double-breasted coat made from specially fabricated cotton developed during WW II to insulate pilots if they had to bail out into the cold sea. As if that weren't cool enough, it's also lined with a vintage-stock Army blanket. Regardless of the era or specific style, these clothes project an all-purpose uniformity--and the irresistibly masculine message "I'm a soldier: Don't get in my way."

A clean and simple interpretation of a nylon bomber jacket. Madison Avenue, New York, September 2007.

British merchant seaman George Meegan, the first man to walk the entire western hemisphere (it took him seven and a half years), wears an army jacket on the trail. 1982. (Getty Images)

An army jacket that could keep you dry--this one's rubberized. Brooklyn, NY, September 2007.

Filmmaker Steven Spielberg wears a leather Air Force jacket (with a Stuntman's Association hat to top it off). 1990. (Getty Images)

English journalist Julian Keeling wears a military-inspired waxed-cotton coat. I wish you could see the red flannel lining. England, June 2007.

William S. Burroughs, captured here by Allen Ginsburg, pairs the authenticity of an Army shirt with the formality of a tie. You can't do much better than this. 1984. (Corbis)

A modern-day, minimal interpretation of a uniform shirt. Spring Street, NYC, September 2007.

I don't usually include film stills because I feel that they project a character's style as opposed to a real person's. That said, this one of Robert Redford as Major Julian Cook in the World War II drama A Bridge Too Far is too good to leave out. 1977. (Getty Images)

Full disclosure: My editor Ned Martel snapped this dude in Copenhagen. He thought I'd like the fedora, but it was the jacket that caught my eye. September 2007.

Mexican General Pancho Villa wore a tailored, more formal version of a military coat in 1918. I hate to use the word chic to describe a man, but it's hard to avoid in this case. (Getty Images)

I've already used a version of this photo in my tie blog, but I'm putting it out there again to show how much personality his coat adds to his otherwise basic office look. London, June 2007.

Director Francis Ford Coppola was clearly feeling the war vibe on the set of Apocalypse Now. The Philippines, 1976. (Getty Images)

I like the addition of epaulets on an otherwise completely unmilitary denim blazer. Prince Street, NY, October 2007.

John Lennon, in his signature look of round glasses and military jacket, belts it out onstage in NYC. 1972.
(credit: Getty Images)

My friend Sebastian in his Marc Jacobs version of a street-wear classic. NYC, May 2007.

I don't know who looks better in his formal military-wear, Pancho Villa or Chiang Kai-shek. You decide. 1957. (Time & Life Pictures/Getty Images)

This guy seems like he walked straight out of an anti-Vietnam War film. Despite the outdated facial hair, he knows how to look good in clothes. Bleecker Street, NY, September 2007.

This is my favorite Elvis photo (I'm not a big fan of his rhinestone-studded jumpsuits). That's probably because his clothes aren't a costume--he was actually being fitted for his Army private's uniform at the Fort Chaffee reception center. Arkansas, 1958. (Time & Life Pictures/Getty Images)

This is the coat I talked about above that's made from super cool high tech WWII military fabric and lined with a vintage army blanket. It's hard to take my eyes off Martin, a member of the Freeman's Sporting Club posse, long enough to actually look at the coat. Chrystie Street, NY, October 2007.

I am a dedicated awards show junkie. I will TiVo just about any gala telecast for the chance to see what the ladies are wearing, and also to tear up during even the least touching acceptance speeches. Yet in all this fascination, I can't say that I ever had any interest in what the men were wearing. Until recently, men's red carpet attire mostly consisted of inoffensive classic tuxedos--black suit, white shirt, black bow tie--which are perfectly tasteful but hardly say anything about the man himself. And occasionally there'd be a guy trying to stand out by wearing something "whimsical"--a western bolo tie, a Miami Vice-style dinner jacket with a narrow lapel and rolled-up sleeves, or a red bowtie with matching cummerbund--all, unfortunately, come to mind.

As I mentioned in my fedora blog, seeing Nick Cannon at a dressy event in May wearing a black felt fedora and long black tie with his tuxedo made me curious to check him out. I have since found lots of photos of Nick in black tie outfits that mix old-school and new-school. He's worn, for instance, a black shirt with a white tie, a white fringed scarf over a white dinner jacket, and a perfectly folded pocket square. Another red-carpet trailblazer of late has been Brad Pitt. He debuted his Great Gatsby look at Cannes in May, complete with side part and low-scooping waistcoat, which seemed new and very handsome though a tad gimmicky. He has since toned it down, to greater success, with messier hairstyles and seventies-inspired three-piece suits. As good as Brad is at many things, I have to give the credit for his dashing new red carpet look to Tom Ford, who has been dressing Pitt of late.

Adding something personal to a penguin suit isn't a novel concept--in the seventies, Groucho Marx threw in a cigar, beret, and thick-rimmed glasses with his tux and, in the sixties, Terence Stamp played with proportion by wearing a double-breasted tuxedo jacket and an outsized bowtie. Maybe it's time for formalwear to be more intrepid, and I'll be there, my TiVo control in hand, ready to replay the feats of daring.

Nick Cannon (with then-fiancée Selita Ebanks) flip-flops the traditional shirt and tie colors to make a more interesting formal look. Cannes Film Festival, May 2007. (Getty Images)

Mr. Cannon again looks modern in an Old World look at the BET awards. June 2007. (WireImage)

Pakistani President Mohammed Ayeb Khan and his wife visit with President and Mrs. John F Kennedy at Mount Vernon in 1961. (Bettmann/Corbis)

Brad Pitt channels Robert Redford in The Great Gatsby with a Tom Ford three-piece tux. He looks undeniably great, but the side part is a bit literal for me. Cannes Film Festival, May 2007. (Getty Images)

Even the smallest anomaly, like Prince Michael of Kent's yellow rose, can add interest to an otherwise basic tux. 1984. (Tim Graham/Corbis)

Pitt again, at his most recent film premiere, in a mellower, yet still highly stylized, evening look. It suits him much better. September 2007. (Getty Images)

Musician Peter Wolf (with his then-wife, Faye Dunaway) looking dressed up in a dressed-down era at the premiere of The Towering Inferno. New York City, 1974. (Getty Images)

Photographer Ryan McGinley is the epitome of cool in his crooked bowtie, casual belt, and Ray-Ban wayfarers. It's rare that new pictures look as good as old ones, but this is an instant classic. The ICP's Infinity Awards Ceremony, New York City, May 2007. (WireImage)

Groucho Marx's tux adds a bit of formality to an already signature look. 1972. (Getty Images)

Brad Pitt yet again (this time with Casey Affleck) goes retro in a white dinner jacket. I especially like the black vest peeking out from underneath. Venice Film Festival, September 2007. (WireImage)

Joaquin Phoenix's worn-in boots give a rugged look to his straightforward tux. Pictured with Eva Mendes at the Cannes Film Festival, May 2007. (Getty Images)

Jean Shrimpton accompanies Terence Stamp, who's in a double-breasted dinner jacket and larger-than-normal bowtie. 1965. (Getty Images)

Blues musician Willie "The Lion" Smith looking seriously bad-ass. 1974. (Jeff Albertson/Corbis)

Even something as simple as a white stripe on a tuxedo shirt can make a formal look less predictable. NYC, May 2007.

Don't these teenage boys look amazing? They're wearing clothes they looted from a tux shop after the Harlem Riots in 1943. (Bettman/Corbis)

My man Nick Cannon once more, making me proud in his very simple but very elegant evening clothes. Cannes Film Festival, May 2007. (WireImage)

The definition of smooth: Ray Charles in a velvet dinner jacket. 1967. (Bettman/Corbis)

You can always count on Jack Nicholson (with Anjelica Huston at the Oscars) to do - or in this case wear - something amusing. They both have a great sense of their own style. 1976. (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)