More of a lurker here, but had to jump in on this one. My hubby is an avid skater...but he's 35...he'd be the plain jane beanie kind. The ear flaps would still be "cool"...however a younger skater I would say would love the beanies with a rim (someone posted some great links) or even a plain one with a pattern on it of sorts (skull and crossbones etc). Stick with darker colors chocolate, black, maybe a dark blue or even deep grey. He'll love it! My DH sometimes even wears his beanies in the summer as it changes the way his helmet fits. He'd prefer to not wear a helmet, but some skate parks require it, so he can still be comfy, not sweaty and "look cool."
I don't have any patterns as I'm a brand spankin new knitter, but boy does lurking here make me wanna knit like a pro right now so I can do some of this stuff too! Back to my blanket I'm practicing on.