I'm 40, I run a bit, I've had plantar fasciitis and I have very wide (4E) feet, so I'm willing to spend a little money on shoes.
For work, I have a pair of Birkenstock Corvallis. I think they were about $120 3 or 4 years ago. I polish them once a year or so. For home, I have indoor shoes that are Birkenstock sandals. I think they were about $100 3 or 4 years ago. For out and about, I've got old pairs of Brooks Addiction running shoes ($120, every year or so).
I went through a Keen phase. They're great if you live somewhere warm and don't have plantar fasciitis. I had two pair, and they lasted very well through biking, hiking, etc. I also tried Kenkoh sandals as a house shoe (~$100) but I've found birkenstock's to be better and MUCH longer lasting.