I could never imagine how putting all these colors together seemed like a good idea to this guy. However -- for me at least -- it really does work. I think it's the light-brown belt toning down the bright primary colors that makes it happen.

Prince Street, NYC, 2008.

While Chris Martin's attire at recent Coldplay gigs has left my husband thoroughly unimpressed, it has left me feeling quite the opposite. Maybe I'm just a sucker for a military look? Or his handsome face? Or his seductive voice? I don't know...but I feel pretty sure that I like his punky, colorful take an army clothes too.

Backstage at the MTV Movie Awards at the Gibson Amphitheater. Universal City, California, 2008.

At a press conference in Barcelona, 2008.

With Coldplay members Will Champion and Guy Berryman backstage at Carling Brixton Academy. London, 2008.

When I was a teenager, I was obsessed with my shoes having to match my belt and my bag. Part of me liked the put-together effect and another part of me was just a little overly perfectionist. As I've gotten older and my style has evolved, I've realized the opportunities that accessories present to show different sides of myself. The same goes for men. If you're a laced-up kind of guy, matching shoes and bag will do wonders to reinforce that. But on the other hand, if your style is a little of this and a little of that, accessories are a great way to tell people more about you.

Were it not for the retro bowling bag, this guy's seersucker and bucks would be a bit too literal for my taste. Spring Street, NYC, 2008.

While his shoes and bag don't physically match, the downtown casual message they both convey certainly does. 59th Street, NYC 2008.

We have a matcher, folks! I really like the more casual business feel of the shoes and bag. 60th Street, NYC, 2008.

I do think this guy's whole look is great -- although there's no doubt in my mind that -- regardless of its laid-back feel -- it was very carefully considered. 59th Street, NYC, 2008.

It seems the business guys like to match more than the creative types. By the way, have you noticed a distinct lack of hard briefcases around? The soft man-bag seems to be increasingly in popularity, even among more formal types. Madison Avenue, NYC, 2008.

The earthy/preppy message is well delivered here through both the L.L. Bean-inspired Whole Foods tote and the worn-in desert boots. Now he just needs to hang out near the Jonathan Adler store and he'll be all set. Broome Street, NYC 2008.

As you're probably well aware, I'm always impressed to see new, more nuanced takes on preppiness. So I'm happy that this look seems to be gaining in popularity. Uptown/downtown, white/black, young/old...no matter the demographic, I've noticed guys taking elements that are so preppy they're almost kitsch and toning them down with simple, solid colors and clean, modern shapes. I believe there are two men to thank for this new take on the predictable, moth-bitten preppy cliches that have been around for far too long. First, is Michael Bastian, a fantastically talented menswear designer who has taken New England menswear classics and updated them with new colors and more stylish proportions. Second is Andre Benjamin, whose Benjamin Bixby line of men's clothes enthusiastically nods to the dandier side of country club sportswear and prep school uniforms. My only advice to offer when trying these looks is...if in doubt, less is more.

Wearing all white to accompany an iconic classic instantly refines and updates this guy's look. Madison Avenue, NYC 2008.

O.K., I admit this guy's cute face may make me biased towards his overall success; however, the simplicity and casual styling of his dapper clothes isn't making me turn away either. Spring Street, NYC 2008.

Right out of the Andre Benjamin school, or should I say academy? Spring Street, NYC 2008.

I like that everything this guy is wearing besides his bold striped tie is mellow and neutral, giving the tie a bigger impact. 5th Avenue, NYC 2008.

I noticed the pants first. Everywhere I look, guys seem to be rolling up their pants -- does it make them cooler (as in temperature)?, I wondered. Or did they just get lazy about taking them to the tailor? Or is it a stylistic thing, a Thom Browne influence? So when I went to look at my stock of photos for answers, I also noticed how many guys in rolled pants were also wearing cotton summery versions of the plaid flannel shirts I saw around last fall...It was kind of hipster thing at the time, but now it seems that look has cleaned up its act (fewer beards -- it must be too hot) and taken on a slightly more grown-up feel. The great thing about these subtle changes is that the clothes are classic -- they're not going to look a step out of place at any time, no matter what the cool guys on the streets are doing, and it shows that small rolling and tucking tweaks here and there can really make a timeless look feel current and more personal.

59th Street, NYC. 2008.

Mercer Street, NYC. 2008.

Mercer Street, NYC. 2008.

Mott Street, NYC. 2008.

Spring Street, NYC. 2008.

I usually wince slightly when I envision a man in shorts — I just don't see guys getting them right often enough. But these guys (both past and present) are starting to make me think differently...their shorts are neatly tailored, and the simplicity of the button-down shirt gives the shorts a more dressed-up feeling than you usually get with shorts.

Mercer Street, NYC, 2008.

John Lindsay, future mayor of New York City. Washington, D.C., 1963.

Mulberry Street, NYC 2008.

Two men playing croquet, photographed by Slim Aarons. Bermuda 1970.

Rivington Street, NYC 2008.

Professional football player Shipwreck Kelly and his wife. Southampton, N.Y., 1940s.

Elizabeth Street, NYC, 2008.

Jacqueline Bouvier and Senator John F. Kennedy at the Kennedy summer house. Hyannis Port, Massachusetts, 1953.