How do I/ should i grow shaggy hair? Do i need to cut my hair into layers to do this?

Ive had the same haircut since kindergarten, and frankly, its pretty boring and basic (EXHIBIT A http://i221.photobucket.com/albums/dd136... and http://i221.photobucket.com/albums/dd136... )

and this is how my hair looks today (EXHIBIT B http://i221.photobucket.com/albums/dd136... and http://i221.photobucket.com/albums/dd136... )

Yeah, i realize its a lil thin in the corners... thank you genetics on that one haha.... but its senior year so why not try a shag or something like that...my girlfriend wants me to and what can i say...im whipped...haha but i have no idea how to grow a shag hair cut... id like to but i have no idea how... can somebody give me some help here? or does my hair not work for a shag? i guess my main concern is do i need to cut my hair into layers or somethin crazy like that or just let it grow out? also, like the part of my hair closer to my scalp is soft and all but the top never gets as soft no matter what... any suggestions? thanks!

How do I/ should i grow shaggy hair? Do i need to cut my hair into layers to do this?

you have to grow some hair first then get it layered