I have several pairs of EG that were around 420 gbp on sale. I have looked at more expensive shoes and liked them, but struggled to feel comfortable paying the 600 - 900 GBP price
I have a pair of Handgrade Sutor that someone gave me...what's that run? $1K? A pair of Church Consuls that are about $600 and a pile of Gucci/Ferragmo that run in the $400/500 range.
Bear in mind, I didn't actually spend any real money on any of that...
$1,200 for a pair of Lobbs I believe. I know I would spend more, but the MTO maker I am after won't be visiting Los Angeles so I guess I won't be spending more just yet.
Shoes - two pairs of BNIB EG Chelseas, for which I paid about $325 a pair (or so) - definitely under $400. Budget was tight for a month or so afterwards, but oh, so worth it. I wore a pair yesterday.
Other (SF-approved) "good" shoes would be my C&J Canterbury brogues, and my PS spectators. I paid about $200 for each (PS specs were seconds).
Everything else (AEs, etc) I have cost me $150 or less.