I go to therapy from work. However, my work clothes are pretty casual - usually jeans with a belt, and a polo or plain t-shirt, and always closed-toed shoes (sometimes steel toe boots, though less frequently at my current job).

Every so often T will comment and compliment - like ask if I'm wearing a new shirt, or something. She often comments/compliments when I get my hair cut.

We have discussed my wardrobe in general, that it is casual but clean, unisex, and not terribly memorable (by intent). I do think that if I showed up to her office in shorts/sweats/a hoodie, etc. she would notice and bring it up. I think she would also notice those choices over something either more formal and/or more gendered and ask different questions.