Could we get a bit more context or explanation for, "Playing dress up doesn’t make you a lady"? I don't know what your intent was but on its own it comes off as transphobic, and you don't strike me as that kind of person.
Actually, it does not come off as transphobic because trans women are not “playing dress up.” Clothing is not what makes them women; they are still women even if they aren’t able to dress in traditionally feminine clothing.
You should bite your tongue for suggesting otherwise, then you should bite it again for trying to put those sentiments in my mouth.
Though you are not owed an explanation, I’ll include one for your edification. All women are not ladies, and the comment was meant to highlight the importance of behavior over attire.