I'm in need of new shoes, but really hate shoe shopping. What are your favorite everyday shoes?

A few things I'm looking for:
-comfortable
-casual
-warmer (if possible)
-fits wide feet

I love boots, and wear those often in cold weather, but I don't need more of those at the moment.

My everyday shoe of choice are a pair of gray chucks, but my feet freeze in them in the middle of winter.

What do you wear and love??

Bonus points if you can give me suggestions on comfortable flats that work for wide feet.