This is the question my wife told me to ask myself when I first started buying things after coming out to her about 5 years ago. Of course, as a newly released-from-the-closet cross dresser I bought too much, too often and discarded so much (always to 2nd hand stores). I think this is a really common phase for cross dressers. As is hoarding of clothes. Somehow clothes become trophies.
I haven't been in that mode for some time but as I was culling out my closet, something I do three times a year, I started to think about what my wife told me to ask myself years ago. "Where will I wear this?" it's a great equalizer. All of the things I removed I had worn planty of times. I don't think more is the answer, but better is. One thing you can wear many times. So now, when I feel like a change up, I head to Rent the Runway, otherwise, I ask myself the question.
So, do you ask the question or is it more of a, "screw it, I want new stuff in my closet"? And if the latter, do you ever ask yourself, "why did I buy that?"