Summer or winter, the grass is always wet in the morning when I go out to feed the livestock. Sometimes it's just damp and sometimes it's dripping wet. And then there is the rain which of course, gets everything really wet.
Some sort of waterproof footwear is required unless you like your feet to be wet. Happily, I currently have three options. My tall waders are beautiful and soft and flexible. But they aren't wide enough at the top to easily go over my jeans. They are great in the summer when I'm wearing shorts because they protect my legs up to the knee from tall grass.
My muck boots are tall ankle height, moderately flexible and insulated so they are cool in the hot summer and warm in the cold winter. They require heavy socks or my feet tend to slosh around in them so I wear them all winter long with my favorite heavy wool socks. I love my muck boots and was sorry they had to cut the left one off my left foot when I broke my ankle last spring. Fortunately, they are pretty easy to replace.
My LL Bean waterproof shoes are new. I bought them when I was in Maine last month. They are shoe height and made of heavy rubber. They are only vaguely flexible. Wooden shoes would be less flexible but not by much. They are heavy and I need light socks if I'm going to do a lot of walking but I can get by with no socks if I'm just running out to the barn and back.
For now, I'm wearing my LL Bean boots most days. And I love them. Of course, next week I may go back to my muck boots. We'll see.