I'm 37. I've been riding since I started with dirt bikes at 7. I've always had a variety of motocross and woods bikes. Interestingly, all of my street bikes have been designed by Tamburini, beginning with a 748 in '98 and including a couple 916s, a couple MV Agusta F4s, and two Cagiva Mitos. My dad has always had a variety of bikes that I also ride, mostly Triumphs, a couple Harleys, a Monster, etc.
The skinny jeans crowd is younger than I am and never understood it. I'm not sure what generation are doing the new "lumbersexual" thing. The whole "land of joy" hipster marketing campaign turns me off. I didn't think that that crowd would be into bikes, actually. However, it's no a big deal and I tend to agree with a comment I read somewhere that all of motorcycling outside of 3rd world countries is a lifestyle thing of one sort or another. What's worse, Ducati marketing towards hipsters or Ducati marketing towards squids?
I ordered an Icon in red because it looks like a fun simple and elemental bike to use around town. It also kind of reminds me of the Yamaha DT250 enduro that my dad had when I was born. Whatever the marketing, the bike looks like it should be fun.