It depends on the situation.
For instance, Dr. Bonnie Jones normally wears a lab coat and glasses (with the four eyes perk i'm roleplaying that she needs them to see) because she's a doctor/scientist.
However if I am in a situation where I need to dress classy for whatever reason I might wear something else for funsies. Maybe I need a speech boost so I wear something with that stat boost.
With my other character, the rogueish smooth talker (I need a name.

) I'll wear fancy suits and what not.