I'm under a lot of social pressure to vary my shoes.
Bottom line: I doubt most males would care what sort of footwear they have on if not for the awareness of how chicks judge them by nothing other than their caliber of shoe. It's as though High School social stigmas never entirely vanish from adult life. Eventually you will be maligned and sneered upon based on how un-hip your shoes are. Indeed, the shoes I wear mark me for the unwavering nerd that I am.
I actually do have trillions of different shoes but I always gravitate back to these (conspicuously in pairs):
-because they are light, inexpensive & extremely comfortable. ...I know, I know, it's crazy.
*The good news is that if you keep wearing anything long enough, the fashion cycle repeats itself and you will suddenly attain "Mr. Awesome" status every 20 years or so. So you never actually have to change your underwear ever again.