Can you help me work out this fashion-ish problem?

My head is spinning with a whhahht? question. During a ping conversation with a woman I learnt s have a particular manner of dress. I also learnt that prostitutes have a particular dress sense. The latter is based on the clean smart manner of dressing and so not as the thinker umes. What's going on in our imperfect world that people imagine a style of dressing holds these meanings?.