I maybe have shopped for casual clothes 2 or 3 times my whole life. I didn’t have a mirror in my room until a few months ago. I love sweatpants, t-shirts, and hooded sweatshirts – mostly hand-me-downs. All this presents an interesting contrast with my other more Polo minded friends: me, in my ripped sweatshirt, Ecko sweatpants (my Mom sometimes buys my clothes at Goodwill and doesn’t know which brands are "black" so I end up with lots of getto apparel), and unbrushed hair, and them, button down shirt, nice shoes, etc. All this is very ironic because with my BlackBerry, pretentious eye-glasses, and loud mouth, I am most unlike my clothes.
I’m told on the east coast the fashion scene becomes even more egregious, with 19-year-olds wearing boat shoes, pink Polo shirts, and brown belts every day of the year. Yuck.
For my business appearances, I DO care a lot about how I look, since I think it makes a big impression. But even in business, I’ve gone decidedly casual since I don’t do sales pitches anymore. But – be careful – give me an opportunity to wear a bow tie, and I won’t let you down.