Dress Cool

Like your life depended on it.

When I was in college, all my friends worshipped David Letterman. He was quick, he was funny, he was snarky before anyone knew the word snarky.

As for me, I was fascinated by the band: Sure, Paul Schaffer was cool, but the band (dubbed "the World's Most Dangerous Band") were all at least as cool: Hiram Bullock (who played guitar barefoot), Steve Jordan (who'd go on to form the X-Pensive Winos for Keith Richards and bring a sense of pop structure to Richards' two solo albums from the late 80s and early 90s), Will Lee (who probably could slay dragons with his bass if he put his mind to it), Jordan's replacement Anton Fig (who looked like a community college professor who was secretly a superhero), and Bullock's replacement Sid McGuinnis looked like the guy your parents would love (who'd somehow always wind up knocking up your sister).

I should've been in that band -- and if it weren't for my complete lack of musical talent, I probably would've been.

In any case, I got this great job in the 1990s which (at the time) I thought was the best job anyone in the world could ever get.

A coworker from the job I was leaving gave me a piece of advice: the best way to stand out in your new job is to dress like no one else. You can completely redefine your identity with some new clothes. She suggested I start wearing Zoot Suits, then everyone would remember me as the Zoot Suit Guy.

But I didn't want to be the Zoot Suit Guy. Thinking about what I wanted to be in this new job, I kept flashing back to something I'd seen exactly once on Late Night with David Letterman. Because what I really wanted was to dress like one of these guys:


(In a more just world, this song would've topped the charts or at least gotten some decent radio play. I saw a copy of the record once for 75 cents in a used record store in Los Angeles, but didn't buy it. When I came back for it the next week, it was gone.)

Oddly enough, this was right after HBO had made the movie version of The Late Shift and I went to a wardrobe sale where they were unloading a lot of the clothes from that movie. I never quite got to be the Zoot Suit Guy, but I did wear a suit that "David Letterman" wore in the movie.

Years later, I realize I've fallen into my own style of dress, a timeless anti-fashion statement unconcerned with the latest trends (or with ironing). But every once in a while, I still put on "Letterman's" suit.

And I still look really cool in it.