These days, being retired, I am usually in a comfortable dressing gown, and slippers or just socks, for a good part of the morning. I usually get up at 3 or 4 AM to spend a few hours writing fiction. Then shower, breakfast, reading in bed, and a quick nap. So it is close to 10 or 11 AM by the time I put on trousers and shirt, LOL. And comfort is the key factor. Old khakis, T shirts, and shirts, usually kept on hangers or folded, but unironed -- often polo shirts, OCBDS or broadcloth. Birkenstocks are standard wear, but now and then I will wear loafers.
As the weather begins to change, I start wearing sweaters and sweatshirts at home, and if I have lunch with friends, or appointments, I often wear a sports jacket. In the late afternoons there is a change of clothing to go out biking, and there too, shorts and T shirts are now slowly giving way to long pants and sweatshirts of some kind, although it is important to be able to remove layers if one gets too warm on a hard ride.
Evenings, I am back to comfortable shirts and trousers, often listening to music or the radio while making and eating dinner, and a dressing gown or old bathrobe afterwards to watch a film or a bit of news.
So that's my cycle of clothing daily. Naturally, being in Wisconsin winters, one's outdoor wear changes dramatically! And it's coming, but first this lovely Fall, and many more bicycle and car trips through the woods.