Lazy Streetwear?

Guys, I need your help with this one. My little brother is a senior in highschool, and is on his way to his first semester of college. Good for him, right? Of course! Proud of him. Unfortunately, he dresses like the love child of a homeless man and an anime loving neckbeard. He wears pajama pants every single day, no matter what. He also wears the same ripped checkered slip-ons and hoodie every day. Now, he's an awesome kid and I don't want people to make fun of him in college for not knowing/caring how to dress himself as an adult. I'd also like him to be able to find a girlfriend if he so wishes.Here is where I need your help. I'm going to buy him a few outfits before his first semester, and he's agreed to give dressing like a functional adult a shot. The thing is, I know he isn't going to wear what I buy him if it isn't comfortable, or at least not uncomfortable. I need suggestions on pants/shirts/shoes/hoodies that are comfortable and look nice. My budget isn't anything crazy, but I'm willing to drop a few hundred at the least. I'd also like to retain some of his interests in his fits. He likes darker clothing and anime/Japanese style stuff. He's 6'1", like 150, and is a good looking guy underneath the homeless fits and unkempt hair/neckbeard. This sub has given me a lot of inspiration with regard to my own style, so I trust that you all can do the same for him. If this gets any support, I'll be sure to post an update with before/after pics. Thanks in advance for any suggestions/help received. via /r/streetwear http://ift.tt/2p2WV2P