Recommend your favorite shoes for walking around in all day and still being comfortable. I'm talking pushing a heavy stroller for at least 2-4 miles, pregnant with lower back pain, comfortable. Recently I've had to start wearing my clunky white gym sneakers every day because my cuter shoes make my back and legs hurt immediately (not like the shoe is rubbing a blister, just tired achiness). And gym sneakers might look ok with athletic shorts, but it's not really the look I go for with comfy dresses.

Since it's almost fall, bonus if they will look good with leggings or skinny jeans and tunics, like short boots or something.

I used to wear Sperry's all the time, but my pair is pretty worn out and the new ones I bought aren't as comfortable somehow.