He just needs to start dressing like an adult.
Different haircut, ditch the dookie rope.
Acquire some attitude, take some risks.
Currently I swear he looks just like this kid I knew in 8th grade.
Yes, Jameister needs to learn how to dress himself by the Styleforum code.
Here are some starting points:
CP Achilles/MMM Gats/Those Boots That Make Your Foot Look LIke A Giant Thumb
High End Japanese Denim/Some black pants with a zipper on it.
An assortment of Wolf vs Goat shirts
Several waist-cropped 100% wool sweaters knitted by the hands of elderly danish fishermen.