Really interesting topic!
I usually go to my T right from work, or I have very little time at home after work before heading out to T, so I'm almost always in my work dress clothes. I've noticed that I have been making a conscious effort not to wear the same thing twice, but my wardrobe is only so big - so that's about to end!

I did wear jeans and a casual shirt and sneakers once. My T never comments, one way or the other.
I usually wear contacts, but I'm wearing my glasses today - I'm curious to see if T will notice and say anything. I think I may have chosen to wear the glasses today because I want to tell T about a breakthrough of sorts I had over the weekend, and I'm wondering if I might tear up when talking through it. But I'm happy about the breakthrough, and I chose to wear a brightly-colored shirt - probably not a coincidence.