I like tshirts and shorts, worn with sneakers or sandals - preferably comfy boys' sandals. My favourite denim gardening shorts started to go in holes, so I covered the holes with applique/embroidered flowers. Now I look like a failed and faded flower power refugee from the 1960s.
When I go out I'm a bit posher - I put on a better Tshirt and linen-look trousers. I did get a nice skirt and a silk scarf for a wedding recently, but the dog chewed the scarf, and I daren't wear the skirt again till I buy some new knickers: well, you don't get the fear of them falling down when you wear trousers, and most of my knickers have dodgy elastic, and I've lost a bit of weight too. I know I should buy some more, but I always forget.
My dress sense is non-existent, and my clothes budget is more or less zero so I'm unlikely to ever get it right. Just as well I live in the subtropics where you wear a lot less, so there's less to get wrong.