New Balance extra-wide or Nike tend to fit my feet. I buy when I need a pair coming up, and I find a ridiculous sale online through slickdeals, usually ~$25-30 shipped. I've occasionally bought Skechers as well in store (checking for sales at an outlet), but I think I should probably stick to the former strategy.
I tried Target shoes once, didn't work out. I expect I'd have similar experiences with other bargain brands. Given the prices I've been paying for name-brand shoes, not much motivation to go that direction again.
For work shoes, I've settled on a set of Dockers that I can purchase through Amazon for about $50. Comfortable, long-lasting, and look good enough in brown or black.
Hiking/winter boots have been a different story. My previous pair of leather Vasque boots was expensive, a gift from parents, and lasted me about 18 years. Supposedly in the meantime they moved manufacturing from Italy to China, and the quality went downhill, so I didn't re-up. Ended up with a pair of Zamberlans, purchased online after showrooming a bunch of different boots. Again, expensive, but if I can manage anywhere near the life of the previous boots, I can't complain. 3.5 years so far.