I'll bump this topic.
I'm always wearing jeans, usually dirty looking from working outside / on cars / lawnmowers / etc but clean. Plain Tshirt or hoodie. I rarely wear shorts in the summer.
Footwear is always workboots in the inter. If it's spring / fall, possibility of work boots but usually sneakers. The sneakers are always what I can get cheap. In the summer, I wear sneakers, sandals or go around barefoot.