Like everything else in T I tend to go thru phases. When I first started I went in casual work attire. I wanted her to think I had it together but wasn't arrogant or fixated on impressing the outside world. I was not very self confident at the time because I was depressed and very overweight. As I got my weight undercontrol and started to feel better about my body. The clothes got more form fitting and included some attention to accessories. Then I went thru a phase where I wanted to just be comfortable and be able to slip the shoes off and curl up on the couch. I never reached this level of comfort but I was ready :-) Now I go in whatever I'm wearing that day.