I think we can all agree TEETH is the biggest thing that stood out... that's the first thing that came to my mind when I saw the pic.
He needs to re-invent his style... he has many choices of what he can do to improve his fashion. I would first recommend a nice button-up ...
actually check out my good friend Erik Shirkey's (The Fashion Jerk) video. In this video he can learn how to improve his teeth (although I also recommend seeing a dentist too) and you can also check out Erik's clothes of what je COULD be wearing.
http://www.youtube.com/watch?v=bi_2_LkV ... Jg&index=8
but clothing style is part of who YOU are so I would advise him to model himself after a successful person of his choice... I can't tell him exactly what he needs to wear... he has to feel comfortable in it. I do recommend he gets rid of the clothing he currently has though!
As for working out... definitely... your friend looks like he's in decent shape especially for his age but working out simply makes you more confident, healthy, positive and focused. He doesn't need to lift huge weights or grow huge muscles.... simply doing cardio can make huge improvements.
As for tanning... tanning helps out but it's not absolutely needed. I'm a pale Ginger and I simply can't tan... I fricken glow in the dark but I date a beautiful black girl... so yeah... it helps but it's definitely not needed if your inner game is handled.
and that goes to the most IMPORTANT thing... he needs to develop his inner game immediately. If he's lost all hope and doesn't have confidence it doesn't matter how good he looks he'll always fail. He needs to fix up his inner game! Wayne Dyer's Audio Books are classic and they really transform your way of thinking.
but even though inner game is your foundation... PERCEPTION IS REALITY and fashion is very imporant.
Here's another example of a shirt he could be wearing... in fact search this website and see if there's something he'll like.
http://www.hm.com/us/product/15880?article=15880-A