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.