My SO is very vocal about his new clothes; so he would say "how do you like my new dress?". Besides, he has so many that I wouldn't be able to keep track of them all. He doesn't like to wear lingerie. His focus is on clothes he can go out in public wearing.

As far as exotic outfits, he likes to wear "wings" at public events like festivals and street fairs. He wears a frilly dress with wings and hopes people will take his picture. He was thrilled at a Lady Gaga concert where he wore a really cute short front, long back frilly skirt (no wings) and women flocked to get their picture taken with him. The other night we went to an adult prom where he wore a beautiful prom dress and was disappointed that no one there took his picture (all the ladies were in pretty prom dresses so he didn't stand out).

He isn't shy about dressing up so I am used to it. He also lets me know how far he intends to take the dressing so I'm not in the dark wondering where things stand.

Yes we shop together, not a really big deal. I buy for me, he buys for himself.