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Croc sandals or another rubber sandal. I always have flip flops in my car and desk drawer at work in case it rains so I can change out of my good shoes in the summer. I also keep a towel in my car so I can dry off my feet.
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Chacos. I took my Hunters with me to Chicago last week, and it was total overkill. I looked like a loon with them on. I didn't see another single person with rain boots on. We went back to the hotel and I changed into my chacos.
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Natives if I'm planning to get wet!
I have Keens too, but they get stinky and make my feet look like troll paws.
I have shortie Hunter boots if it's warmer and I don't want to get wet, but know the puddles are deep.