It’s not fucking rocket science.

If you’re invoking the bad tropes then you’re invoking transmisogyny.

If your character is dude coded and wearing a dress the following tropes are going to be a fucking problem

1. Absurd Joke Character That Is Rarely If Ever Serious (this will make the dress wearing a joke to the audience)
2. Character Is Wearing A Dress To Fool Someone (deceptive trope)
3. Character is Predatory at any point during the course of the series even when not wearing the dress (predatory trans woman trope)
4. Other characters find it funny (trans women as jokes trope)
5. The character wearing the dress finds it funny (trans women as jokes trope)
6. Other characters find it disturbing (combo of predatory trans woman trope and revolting trans woman trope)
7. Character is normally revolting or gross or has gross out humor as a main character trait (revolting trans woman trope)
8. Character wearing the dress finds it disturbing (revolting trans woman trope)

There’s more too but those are typically the only ways you see a dude coded character in a dress so don’t fucking pretend please.

And with the context of our shitty society, you’re going to need to be pretty blatant about this being a serious and important and needed exploration of self for a dude coded character to wear a dress. Something the other characters take seriously and find important to that char. 

And even then it could still backfire if you fuck up a little.