i don't worry about staying warm. doesn't get cold here until jan. we have some cold days in nov and dec but i just dont' work on those days since work slows down during leaf time anyways.
i don't wear facewear of any type unless i'm going snow skiing. lol
i use 3m foam earplugs all season long. i wear stihl or husqvarna sun/safety glasses when i'm mowing grass. during leaf season i don't wear glasses because they just get covered in dust and you can't see and you have to keep wiping them off. it's best just to not even wear them during leaf season in my opinion.
i don't wear gloves while mowing or doing leaves.
as far as clothing i wear khaki pants all season long. in the spring/summer i wear tshirts and in the fall i may wear a long sleeved tshirt if necessary. i wear tennis/running shoes all year long. boots are too hot and uncomfortable.
now if you are talking about working in the snow then that is another story altogether.