Waterproof shoes for fall/winter walking
I wear my sneakers all the time. They are particularly comfortable for the 3.6-mile round trip that is home to daycare to work to daycare to home. We love this walk! We go through the University of Kentucky campus, which has interesting landscaping and lots of paths to explore. We've been doing this since we changed daycares in April. There's even a grocery store a few blocks from our route, so I can pick up emergency bananas if we run out. (Danger! Never leave the house with toddlers and without bananas!)
It rained on Monday and Tuesday this week, which reminded me that sneakers with mesh panels at the toe are not the best thing to walk in when it rains.
Can anyone recommend good urban walking shoes (mostly pavement, some grass and packed dirt paths) that are waterproof, have wide toe boxes, have good arch support (or removable insoles that I can replace), are comfortable enough for all-day wear, and are cute? I have a pair of Keen boots that I like a lot, but they are well-worn and probably should be replaced.
Actually, if you have recommendations for insoles, too, that would rock. I usually just get whatever brand the shoe store sells. Sometimes they work out and sometimes they don't.
ps. I loved all the great advice on the "what shoes do you pack" thread!