Once upon I time I explored the philosophies of hipsterism on this little ol' blog. You can read that here if you haven't already. I also, in that post, asked the deep cutting question, "Am I A Hipster?"
I'm pretty sure the answer is no. Especially because of this experience I had recently:
I rode my bike to go put something in my friend's mailbox. She lives just down the street. I didn't want to go all the way upstairs just to get shoes, so I decided to go barefoot. Well, sockfoot. (Black with polka dots. I like them a lot).
I got there just fine, but then when I was going back uphill to my house I remembered how bike pedals are kinda spiky and like to prod into your feet in a really ouchie kind of way.
That will probably be the last time I ride my bike without shoes on.
I don't even know if it's hipster to ride a bike barefoot, but it seems like it might be.