I'm 38. The Scrambler Icon I ordered will not be my first bike, and like JustKip I was considering a Monster before discovering the Scrambler. While I do have a beard (I've had it for 8+ years) and wear flannel (hey, I live in Minnesota), I don't wear skinny jeans and I'm not a hipster. I'm probably not far off their demographic though.
Stepping on my soapbox... I also have far less of a problem with people that might be labeled as hipsters as I do with the term and the people doing the labeling. I'm not sure why some people have so much hate and anger toward the demographic. I didn't even realize it was as bad as it is until the whole Scrambler whirlwind and the backlash to it that I see so thick in the comments on every single article. People need to lighten up and not worry so much about what other people wear, what music they listen to, and how they like to go about their life. Stepping down off my soapbox...
What pulled me in on this bike is what I see as the simplicity and casualness of it. I had Triumph before, but wanted something more sporty this time around (and specifically wanted a Ducati). I was pretty much all in on a used Monster, with my only hesitation being that it was just a tad more sporty than I had in mind. I was just waiting for early next year to start the real hunt for the perfect yellow one.
The funny thing is, since I don't really follow motorcycles much, I didn't even know the Scrambler existed until an article popped up on Jalopnik on December 11th. It only took me until December 18th (the day before my birthday) to go in and put down a non-refundable deposit on one. Maybe I'm a little impulsive, but I knew immediately it was the bike I wanted.
Now I have several months of Minnesota winter to endure while I obsess about it.