This is a fashion question but maybe it is my age - I just go for comfortable leather shoes, nothing fancy to look at - There is an Irish brand called Clarks that suits me plus they have a couple of shops that are handy for the "Surgical Strike Shopper" like me, maybe every couple of years I go in and say I'll take them, them, them and them size 10, five minutes, shoes to keep me going till next time.
Sketchers. Their shoes are great in every way. They are so comfortable and feel soft, they keep your feet dry in the rain and have so much traction in the wet even on painted lines on the road or wet metal.
Converse, they go with everything. Have some red high tops, and low cut blue ones with black trimming/laces. Also like DC and other skater trainers but the more plain looking ones, because they are so comfortable.