I fancy myself in the top left. I'm an elite road racer and my team supplies me with my clothing and some of my other accessories if I race and volunteer enough during the season. No way I'm forking out premium $$$ for Rapha, Assos etc.
When I see people looking like they came out of a cycling clothing catalogue, my first instinct is that they are a poseur. Of course I've been around long enough to know that there are plenty of "skilled" cyclists that like that sort of thing, so I withhold final judgement until I get closer and get a good look at someone. I can tell more about them as a rider by the way they ride their bike, even a low cruising speeds. There are always "hidden savages" (as I like to put it) in layman's garb and baggy shorts that can put down some big watts for extended periods.
If I don't get something for free, you can find me in the bargain bin. I dig "the black bibs" for this reason and have worn through a few bibs. I need another pair actually.
The same applies to my equipment to a large extent, mostly heavily discounted, lent/borrowed from my team's shop sponsor to ride for a season, or bought from a buddy. Although I am putting together a new XC MTB from largely new OEM parts at the moment.
Bottom line is I agree with
burnthesheep, bikes are cool (All bikes), riding is cool, I might think these things to myself but I won't let that prevent me from striking a conversation with whomever I encounter out on the road. Between road, TT, track, MTB, BMX (younger years) and street fixed gear/fixie riding (also younger years) I can talk shop with most riders and encourage anyone riding a bike. More ridership on a bigger/macro level is good for all of us. I usually smile and wave
unless I'm in a bad mood or pissed for some other extenuating reason. If you wave at me - I'll always wave back!
Ironically it's the less experienced or lower category racing cyclists that tend to perpetuate the elitism and disdain that roadies are so known for in other cycling circles. They have the most to prove.