The only time I think about what I wear is if I haven't been bathing, it is cold outside, and I have the option of putting on a hat to cover my unwashed hair. Otherwise, I don't think about it.
I am not at all observant about what people wear and couldn't tell you what the therapist was wearing one minute after I left her office. The only exception might be if she wears boots that I like. Oh, and I have noticed a leopard print jacket hanging on the back of her door that I think is hideous. I haven't seen her wearing it, though.
I don't recall her every commenting on my outfit. One time C went to therapy right after going to traffic court, and the therapist said she had never seen her in heels. We don't dress up for therapy and being an undergrad requires no special outfit. So when it's warm, we tend to be wearing a pair of Nike Tempo shorts and a t-shirt. When it's cold, the shorts get switched out for sweats or leggings. Due to wild fluctuations in weight caused by going on and off new medications (or failure to take thyroid meds), none of our jeans ever seem to fit the way they should. We do have dresses, but it does not appeal to me to wear a dress to school or therapy. Living on the coast means it is often windy and wearing a dress would carry the risk of having a Marilyn moment. Very occasionally, we'll wear a pair of stretch jean shorts or stretch jean capris and either a t-shirt or blouse. Today, for instance, I am wearing the jean shorts and a blouse. I don't know why I switched it up today, but it isn't because I have a session later - although I probably would have picked something ill-fitting and ratty if I was planning to stay home all day.
Shoes are usually my black Converse low tops, but sometimes other sneakers, sandals, or boots.