All the time! I wear panties everyday, panty hose or stockings in the colder months and a bra whenever I can comfortably hide it under my clothes. I almost always wear womans jeans, my favorites are "old navy" ultra low rise size 10's. I wear womans top's when I know that I am not going to take my sweatshirt or jacket off. As for bed time, it's all the way for this girl.