Interesting topic. When I knew I was going to discuss my feelings/attachment to my T, I wanted to wear more sophisticated kinds of clothes because that's what she always wears. I wanted to look my best so I would feel more "equal" to her. But when I had important issues about something else other than "her and me" I wanted to dress as comfortable as possible. I didn't care, as long as I was clean and neat. In general. I thought a lot about what I was going to wear to my session. Sometimes I wore something new so that my T would compliment me.