I wear jeans, t-shirt, and a ball cap on backwards about 95% of the time. I get comments all the time about it because of my position. I own a company that employs 35 people and made a lot of money last year but I don't dress the part. I love the look on people's faces when they see me get out of my BMW or H2...it's classic. Most people think I'm a drug dealer!
My girlfriend suggested that I joined eMerge and start dressing in slacks and button down shirt. She even commented on a tie. She's an accountant so she's used to seeing people in monkey suits.
Starting this new year I think I'm going to ditch the ball cap and jeans and start dressing up. My employees respect me because I have a layed back personality but I honestly think it affects my professional relationships outside of my work.
How do you dress and does it represent you well?