Simple question: In your opinion, what should a guy's liquid net worth be before he can "afford" $500 shoes? (Your answer is a number) Conversely, below what level would your natural reaction to his $500 shoes be: What a jackass! First, please note the use of quotations above. This is not a literal question. (eg: When he has $500.01, duh!) That said, $500.01 certainly is a valid answer. I am using net worth and not salary because the latter can be a very weak gauge of one's financial solvency. Free Cash Flow (FCF) paints a more direct picture. I also deliberately picked the $500 threshhold, and not $300 for AE's, et al. $500 is a different pricing paradigm entirely, and is probably 3 SD's over the average shoe expenditure. At this level, one has deliberately groomed himself as a "serious shoe guy". So, at what point does a guy have no business wearing $500 shoes, and be viewed as a fraud/idiot? Alternate question: What other criteria would you use in deciding whether a guy can afford $500 shoes?