For me, as far as comfort or looks... most of the time it's comfort. It depends on the situation.
I'm a quasi-shoe slut. I like to have many pairs of shoes, but I've been able to dwindle them down in the mass moves the past few years. in High school I have about 40 some odd pair of shoes... between all the activities I did ... they were almost all well used.
Right now I have maybe 10 pairs... three that are still in Arizona that I probably will either replace on my own or pick up when I go out there. And the others I have here... I've got sandals, flip-flops, tennis shoes, and a couple of nice pairs to wear with decent out fits that I don't wear often.
I mainly just wear sandals and tennis shoes. Though I've really grown to dislike wearing shoes at all... I still have a weird thing for owning a few more than I really need.
Most of the time I just like to slip on something that's comfortable and easy.... so sandals and flip-flops are primarily what I wear.
I need to replace my doc sandals though....
Just too expensive to replace right now. I really want to get a pair of thigh-high doc boots... but that will come in time. If they only had Rocky shows here in Richmond... I'd be set. "sigh"