The most comfortable pair of shoes is NO SHOES. I like to sink my feet in sand and walk shoeless on a meadow till I realized the importance of shoes when I was 14... which I stepped on a piece of broken glass hiding between the grass
My black combat boots are my most comfortable pair! They're great for working in theatre tech (where you have to wear all black during performances) and for this one time I cosplayed as Jane Lane at school, but because nobody I know watches Daria, they just thought it was a really cool outfit. My favorite pair is my high-heeled sneakers because they make me feel really tall and fancy.