Well, make it fun. My wife calls the shots. When she wants me to dress she’ll have laid-out what she wants me to wear in the second bedroom (my closet) and tell me to “Go dress”.
And she inspects my makeup to see if I’ve got everything right.
As she says, “I’d rather be looking at a nice looking woman than a guy in a dress”.
My wife is in charge and it’s been that way for about 20 years. There have been times where weeks went by without dressing and there’s been times when she wants me to dress for her for a couple of weeks straight.
We go to the mall together and out to eat. She does the ordering.
It’s worked very well for us.
