Beauty is in the eye of the beholder, and some shoes reflect the budget a responsible person should wisely adhere to. Hence, someone with champagne tastes on a tap water budget may admire a pair of Manolo's like I gaze at a hundred million dollar Picasso in a museum. Lovely, but not meant to be mine. I can, however, get the postcard in the gift shop.
That being said, I've seen $2,000+ pairs of shoes/boots that I'd never get regardless if I topped the Forbes 400 list.
Some footwear lovers are constricted by foot ailments but nonetheless love the look of stilettos. So they wear what doesn't torture them.
There is a pair Marsell shoes that is hideous, but I actually like, even though they look like they've been run over by stampedes of tanks. Even at 60% off, they're still $300. Err...part of me says "go for it!" while the rest of me says "they're ugly, but in a kind of cool bashed-in-pug-dog-nose way".
On a side note, I hate flip flops. Really. For two reasons-I just don't like them, and they have sent countless people to emergency rooms by breaking, or catching on steps or other things. To traipse from my hotel to the pool, I use slide sandals. Apart from a pool destination, I don't even wear them.
There are lots of things I think are "ugly", or frivolous-like some collector's items, but then just move on. Who knows, a day may come when you begin to like what you used to think was unsightly.