I know that man clutch Gucci bag is just horrible, and I don't even know what kind stuffs you want to put in there, that your pocket cannot hold.
As far as the watch, I know that Delacour has been sponsoring some soccer players, so I guess that watch is free, so why not wear a free $20k watch?
Even David Beckham (some people refer him as the fashion trend itself) wore Jacob&co diamond watch. I don't really see if there is anything wrong with people wearing extravagant diamond watch with horrible movement or shape, as long as you love it.
I also think that Gucci leather jacket is actually looks pretty cool and badass on him. lol.
That pearl necklace might just be a gift from his loved one, because for more than $500,000 salary per-week, I probably wore a diamond necklace, not some pearl ones.