Not many women are going to feel sexy in underwear that brings to mind a balding man with a beard and plentiful body hair.

This is probably true.

Most guys aren't that into all of that anyway, but they'll buy it for women it it makes them happy.

The absence of these peripheral details is rarely a deal breaker.

Not many men are going to feel turned on seeing their girlfriend/wife dressed up like a balding man with a beard and plentiful body hair.

Man are generally goal/target oriented. It's unlikely they'll be thinking of the foolish weirdos wearing similar things.

If a man sees a woman in a revealing outfit, he's definitely not recalling a weirdo in drag who may have worn something similar.

However, I could imagine a woman making that connection to someone else wearing a similar outfit.
I've seen "Who wore it better" in magazines, so maybe that concept applies here.

Instead, the weirdos will buy it and wear it themselves in private, or around other weirdos. Unspeakable things will occur, and it won't be cool.

And perhaps they'll also wear it at the library while reading books to the children of tragically negligent parents.