As far as first impressions go, do you read much into what someone is wearing and use the stereotypes for the style that they are going for as to what type of person they are?

I am meeting some new people next week and all they know about me is I love music and tend to be a hippy at heart, but I like to look nice and I think my choice of clothes might send the wrong message. I want to be myself and comfortable. EX: Does it really matter as long as my shirt doesn’t say “suck this” or my boots don’t have flames on them?