Hipster: Teenage Wasteland

Game description from the publisher:

Strategy is the name of the game as you compete to be the coolest in town in 'Hipster: Teenage Wasteland'. Collect your gear and play against others in your quest to be hipper than everyone else. But watch out, because once things become too cool they're no longer cool. When stuff becomes too cool it goes away, replaced by newer, cooler stuff no one is into. If you're gonna win, you gotta be on the cutting edge! Can you be faster, can you be cooler, can you be Hipster?