Well, if I'm going running, I wear running shoes.  I almost never wear the girly ones unless I have to dress nicely for an interview or some bull shit.  During summer and fall, all I wear are my Reefs or Quiksilver flip flops.  When it's raining or really cold, I'll wear a pair of the skate shoes.  Different pants fit better over different shoes, etc.  I don't know, I usually just grab what's in front of me and bolt.