The most comfortable shoe i have ever owned is the Air Jordan Retro 2 Low Top. The width is slightly wider than most other Nike shoes and you're basically walking around on air all day. Every year they come out with a new color combination so they are easy to find.



I have also been buying late 80's early 90's retro shoes from other manufacturers. Diadora/British Knights/Lotto/Fila/Puma/Troop. You can usually find these on amazon for $20-50 a pair. They are all what i would call "skate shoes". Obviously nowhere near the comfort level of the Jordans but they fit well and are usually light weight.

Some of the shoes that were popular when i was growing up...