Speaking of Brianna hair: it really looks like an intentional jab that the picture is posted with this headline. Do they hate him at HuffPo, or just some editor just couldn't stop him/herself? He looks like his hair is unwashed and uncombed. With split endings. It looks like it never saw the inside of a hair salon.
Seeing many pictures of John, I think with a help of stylist he could really improve his appearance. (anybody can, and here is a huge room for improvement

)
First and foremost he should come to terms with the fact that his hair is too thin to keep it long, and either buy a high quality wig, or cut it to a presentable arm length bob.
Current styling doesn't look good with his pudgy face. He definitely should lose weight, and invest in some lip filler, just don't overdo it. His lips are nonexistent, to the point that lipstick just accentuates their nonexistence.
There was a lot said about clothes, and so I'm not going to repeat it. I'm going to focus on his face: one of the reasons that he is so obviously non-passing is that he did nothing to his bushy manly eyebrows. The current trend is to have rather strong eye-brows, he could use the trend for his advantage, to draw attention away from his less desirable features.
About make-up: he doesn't know how to apply it, that's obvious. But still, his eyes are not small, and it could also be used to his advantage. With skillful make-up, and daily training to stop open them up like a moron who got scared of a ghost, he might start looking presentable.
After all these improvement he would still look at best as a middle aged accounts payable, but at least he would not scare people on the streets.