What am I missing here? It looks sloppy and disproportional to me.
I don't know, but this is one of the best fits I've seen in a day or so. The jacket definitely has some features which are not on your normal straight forward wind breaker that make it stand out. Everything fits really well. He's a very skinny guy and dresses to his body type very well.
Not getting "waiter" at all - that is excellent. The full-cut pants look really great, and the mandarin collar is fantastic. Simple, but really, really, really good. It helps that the photo context is perfect. I think you should start adding some fabric close-ups, though.
a slouchy DB jacket would look really good on top of it all, I think - MMM has done a few, and *duh*yohji*duh*
maybe you could do something in the way of some different (funkier?) shoes to push away from the waiter-esque vibe. It does have that resemblance a little but still looks cool. btw... I have a few Mandarin collared shirts and always dig them!
lotto is mad taxable, and some winners are retarded and get all the money at once, instead of getting installments over the years + interest. Yah, at certain interest rates it might be better at face value, but taxes really complicate it in the long run.