I am so flipping neurotic about what I wear to sessions! If T knew I think we would spend a week of sessions processing how crazy I get over it!
All clothes are washed, usually in their own load, the night before. I have one pair of designated T socks (I take me shoes off) that are a dark pink carhart sock (clearances at work, feminine but bulky wool blend). Either my sneakers or my blah leather flats (same brand T wears but a women’s shoe instead of his boots). I have two pairs of jeans, dark dye and a comfy but not frumpy fit. Winter is layers... lots of comfy, concealing layers! I used to wear bulky sweaters or a sweatshirt but then T complimented my sweater one session (appropriately) so it has been sweatshirts since. Summer is polos TUCKED IN!!

(see rant in what your T wears for why I emphasize tucked in). Sometimes I will be confident enough (or just too hot) and I will layer with a tank top with a super light cotton shirt (long sleeve) over the top and tied at the waist. It looks like it is going to be a really hot and humid summer here so I *might* have to break down and wear ankle length, loose skirts. Heat and I do not get along.