it's a bit easier if we look at it from the outside...
We are all so close to this issue. Maybe I just have been incredibly lucky:
My first shopping trip for Tina was with my wife, who was taking us out to buy a skirt and thigh highs. The choice was totally my wife's as this was all new to me. She picked out a short skirt (incredibly short, actually), held it up to me and proclaimed it should fit nicely. We then went to a different section and picked out some stockings. When we go to the checkout I paid and off we went. No one bothered us and I just filed it away.
So now when I'm in a store like Target or any other large general store, I see no reason not to purchase thigh highs, or peruse the racks for tops or even bras. After all, if I get asked if I need help I can just say, "no thank you, I'm just looking", or "I'm ok". If I'm asked who I'm looking for, it depends how far from home I am. I'm I'm traveling I have no problem saying it's for me. If I want to try something on and I'm in drab, I just take it into the men's fitting rooms.
Just seems so normal!
tina