Even in Purgatory she's wearing distracting strips of cloth or mesh that she insists counts as clothing. He's gotten used to her offending his sensibilities that he can make eye contact without letting his gaze wander or anything else distracting him too much.

"If you were tired you don't need these. What if something were to happen to you while you were alone in this house?" Mr. 'there was a lot of opium' Holliday isn't going to say anything blatantly hypocritical about her newfound vice. He's never said a word about her drinking either and he appreciates that she has returned the favour. But this is too far.

"Wynonna, this place... we are unarmed. All manner of things have been trying to kill us. It isn't-- safe or good for you to be taking anything you don't need to be taking."