I was in Seattle for work last week and we chartered a boat for some afternoon entertainment. Seattle is so pretty in the summer! The only time I think twice about what I'm wearing is with clients. I'm scarred from my college communication classes: "If you're too dressy, that sends the message you think you're better, too underdressed, you're saying they're unimportant." The conclusion I have drawn from this is that I will do the following: wear whatever the fuck I want and hope for the best.