I have wider feet and I hate having my toes smooshed, so for shoes I only wear Keens, they look chuncky but I have never worn a more comfortable shoe. They sell them at places like REI, an while they may seem pricey I still have my first pair I got back in 2001 and they are still wearable. I have a total of 3 pairs I have been switching between for the past 10 years and they are all still in good shape, so they really hold up and last.
For winter boots I found a pair of red quilted Sorrels I absolutely love! They are very comfortable and give my arthritic knees decent support.