Thick Beanie in 90+ degree weather that clashes loudly with a suit that you shouldn't be pairing with any beanie in the first place. 
Suit either poorly fitted or not tailored to fit at all.
Ultra Casual suede loafers that also clash loudly
Buttoned up bottom button 
Best of all, Tim has this look that betrays that in his own he's absolutely slaying it with this look. I'd put money on a bet that the suit is probably from some over hyped designer brand (likely Armani because ...... Tim).
The fact that he is so insanely rich will not stop being astounding to me. Most efficient system of distributing resources btw
I didn't know this at all. Did it come from streaming or old money ?
He's made millions from streaming, somehow
Streaming, and his "journalism" (he was paid by fascist billionaires to run stories on how evil auntiefa is, about Muslims in Europe and how they're replacing white people etc. He then pivoted to commentary (which his audience calls "journalism" too) and reacting to shit from the daily mail, cnn, fox etc to whine about the "left" etc. He does it while being a whiny little beanie boy. I'm not sure how he's maintained and audience, but I guess posting pro-bourgeios, pro-fascist propaganda pays well.