In short no, If you are taking me to a specific event or venue, please give me notice of what the dress code is going to be, black tie, smart, casual etc.

For other dates, if there is soomething in particular you like, do tell me, and i'll try and oblige but cant guarantee it! I.e. skirts, suspenders , boots etc.

For you, i'd just say a date with someone who is clean and wearing clothes he feels good in, is always going to work best.