I'm an "all or nothing" crossdresser; when I was getting ready for my first time out in public, I wore panties and tights or pantyhose under my pants for about a week, but that was just to psyche myself up. Never did it since.

There was one time in 7th grade when my mother mixed my sister's underwear with mine and I spent the whole day wearing lacy girls briefs, but that was a complete accident. It was also one of the most nerve wracking days of my educational career!