I bought these Gap ankle booties last week and I have. not. stopped. wearing them.
While our quest for the perfect black booties is still ongoing, if you're not married to the color black then I would highly suggest these guys from Gap. They're super duper comfortable (as in I walk to and from work, almost twenty blocks each way, and don't want to kill myself) and have a sort of sophisticated Western vibe to them. Also, for whatever reason, Gap is totally underrated when it comes to shoes (in my opinion) so not everyone and her mother will have these.
Of course, I'd be lying if I said price wasn't a huge, if not, deciding, factor: These babies will set you back only $80 and, unlike a lot of under $100 boots, they're made out of 100% cow suede and leather. They don't look cheap and they feel sturdy. When I wore them out this weekend three people asked me where I got them. So yeah, now I'm telling you.
Go get them here.