How to Dress the Part As an Entrepreneur The T-shirt-and-hoodie set is changing the rules of dressing for work.

Is it better to overdress or underdress?

Weird question, first of all. Because it implies that looking stupid is a certainty, so you might as well pick in which way you will look stupid. Also, it's a little repressive. T-shirt or suit. Shorts or khakis. Hoodie or opera cape. It's like having to pick salt or pepper. Or Salt or Pepa. Why must one choose?

Fine: It's better to overdress. Because by overdressing, you don't at first appear lazy. (If indeed you are lazy, why not push off the inevitable?)