There are some stereotypes that are perpetuated by older films, photographs, and cartoons—images of a university professor with a tweed jacket with elbow patches looking contemplative with a pipe instantly come to mind—people instantly think of an intellectual; older gentlemen are often depicted in older films with pipes, so it's ingrained in the culture in the US (and beyond) that pipe smoking is not something younger people indulge.
I must admit, the times I've seen some twenty-something hipsters wearing 1940s period clothing and smoking a pipe it seemed like they were trying too hard and was an affectation. But, who am I to talk? I have a handlebar moustache and waist length hair. Does it really matter? As long as people are enjoying themselves and not hurting others, it's all good. It's a good thing when people are confident enough to not care what other people think. I'm currently shopping for a fez to wear.
When I would see groups of young guys smoking expensive cigars in public, puffing like freight trains and making huge clouds of smoke, it would bother me. I wanted to explain to them that they were carbonizing their tobacco and not getting the flavour they had spent so much money on. I do think there is an association with status when it comes to cigars, again much to do with film media over time and collective memory.
I mostly smoke my pipes at home. I'd be too worried about dropping and damaging them on a sidewalk. The few times I've gone to a pipe club meeting, I've brought less precious pipes (not quite beaters or baskets) with me. I find it's easier to have a conversation with a cigar than a pipe. I share pictures of my pipes here because I suspect there will be an appreciation for them. But, generally speaking, my pipe smoking experience is a solitary one—no one sees or cares about the pipes I have or smoke except me. Sure, my girlfriend and a friend or two might see me smoking, but for all intents and purposes it's just me.
Just one look at the membership of this forum and you'll see a wide range of people from disparate backgrounds, and interests. The biggest common ground is we enjoy pipe tobacco and pipes, with many differences within.