@considermycat I did this (dressed as a woman for Halloween) in... 2010.

I'm nonbinary, not a woman, but still.

@ryanc @considermycat ditto. I did this in the late 90's and early 00's, and now nonbinary.

With that said, depending on where the person is in the "exploration" phase I would say offering transition info could put them into defense.

I would probably rather just compliment their outfit, etc... Give them the possibility to swim in some gender euphoria. <3