I think people do judge, but it definitely depends where you live. When DD was born, we lived in a relatively 'posh' area of SW London and everyone (apart from me!) seemed to have a Bugaboo Chameleon. I think it's also fair to say that a big price tag doesn't always equal great quality (see below!)
Roll on two years, I'm PG with DC2 and we're now living in the USA. Bugaboos are popular here, but there's a much wider range of prams and pushchairs available in general, ranging from really very cheap ($150) to $$$. Uppababy is massive here and have great products and fantastic customer service. I can't really judge too much as I don't know half the brands though and I'm currently looking on Craigslist for a second hand double - probably a Bob or Baby Jogger (v popular here). There seems to be a lot more selling on of baby stuff here than in the UK - even carseats, which seems crazy to me.
Personally, I bought an iCandy Cherry first time round and it was the biggest waste of money EVER. Wheels had a design fault, got replacements, they fell off every 100m or so... If I hadn't moved overseas in the meantime, I'd have taken legal action against iCandy as the whole contraption was dangerous, and given that including all extras, travel bag, bassinet, footmuff etc, we're talking the best part of £800, I would have expected way, way more. Conversely, my £80 Maclaren umbrella stroller is AMAZING. And interestingly, none of my Bugaboo-toting friends back home had problems with their products - make of that what you will. Sometimes a product's reputation and price tag is well deserved, other times it's a massive con.