This is Tsubasa Senpai from Gakuen Alice.
He has the Alice of "Shadow Manipulation" like Shikamaru from Naruto. HA!
He first shows up in Volume 2 and meets Mikan Sakura.
This picture takes place when he's in the tree just woken up from his sleep by shouts made from Mikan, Natsume and some seniors.
In the picture he's holding his hat but I didn't bother drawing a hand or an arm so whhatever.
To me he looks like Hotaru in my picture (Get Hit)
I don't mean he looks like a girl...just in my picture. (Gets Punched)
OW! That HURT!
-runs at light speed.-