There's a book that came out last year called "Crap Towns" and they've updated it with a second edition this year. Funnily enough, Windsor is the second worst town, apparently, in England because people think it's snobbish and ostentatious.
I was pretty amused by this -- to me -- typically English reaction to Windsor. "Well, those chaps in Windsor all make too much money and have nice homes, it's terrible, terrible place to live." Since there's a town filled with people who are nominally successful, they've simply had to vote it down because it's too nice.
Reality, however, couldn't be farther from this so-called Crap Town truth. Windsor is filled with people who are very approachable and friendly (and far more so than a variety of snobby places I could name in the states) and homes that are not overtly flaunting their wealth (vs. some other nearby towns with what appears to be McMansions in 'em).
It's a bum rap -- but it's a keen moment of insight into the psyche of popular Britain where the average person believe Windsor to be "quite posh" and subsequently anyone who lives there needs taking down a peg or two, simply because they MAY have been a little successful in life.