I wear flipflops in the summer. My chickens peck pretty gently, so no worries about getting henpecked toes. I've got fake crocs, but everything I put on the front porch gets filled with spiders, so I prefer flipflops. The crocs fill up with nasty bugs fast.
For winter, I bought a pair of rubber boots, but I got them too small and they're hard to slip on and off. I'm going to get another pair, a few sizes too large, just for the coop. The spider issue isn't so bad in winter, so hopefully I won't be too afraid about putting them on.
As for clothes, I wear just about anything. I don't buy clothes that don't wash well, so I go in there in anything from pajamas to dressy work clothes.
I use a natural bug spray on my legs, because I'm in sundresses or running shorts a lot of the time, and I get tons of mosquito bites. I don't bother with gloves when I clean, just wash up well when I'm finished.