Im not sure I understand some of your points
I wear the same clothes year round. I dont wear shorts or t shirts to be fair. I wear trousers only and tops/shirts
I have lighter clothes for warmer weather but I feel the cold terribly and have poor temperature regulation. So I go out with thermal vests on quite a lot of the time, even when in Spain. I nearly always have a scarf with me, gloves and often a jacket
So last night, I had nice lightweight wide leg ankle length cullottes, a vest, a shirt, a smart jumper. I had gloves with me but forgot a jacket, I was cold coming home, we sat outsicde in the restaurant garden. I didnt have a scarf either and regretted that.
Yet in the day we had been swimming, with a rash vest and then my wet suit over the top so I had my loose viscose flowy trousers on the way there , and then the dry robe which I travelled home in.
In doors yesterday I wore a different pair of loose trousers and a sweatshirt as I was cold after swimming and then turned to boiling later.
I had about 4 changes of clothing yesterday
I wear mostly black although today is based around navy blue. I dont know what I'll wear tonight, I dont want to wear the same thing as last night.