Of course skateboarding in itself doesn't necessarily make one cool, but if you're already a smokeshow then yes it will probably add to your superficial appeal for a fair amount of people.
need I remind yall how Peter Parker used to look? Clearly there was a time when he wasn't such a snack. Liz here is even scoffing at the idea of inviting Peter to a dance because he appears so lame.
After the spider-bite, he started gaining confidence and grew into his looks. He was never ugly, but before he got his powers he had a kind of meek, wet blanket-vibe.
I'm not saying that Andrew Garfield is too hot to play Peter. On the contrary, I think he's a perfect choice. But if he's 27 years old and at his peak-attractiveness, maybe he shouldn't play the teenage wallflower version, but rather the later Peter Parker who is popular with the ladies? Like it's not just that he's good looking, it's that he's attractive like a 27 year old, in high school. But we're to believe that girls before Gwen weren't all that interested.