ok, the rain boots is a bit extreme but a FEW of the outfits are actually ok (by themselves). Once you hit the age of 35-45 + and you roll around the crowds of men who pay 15+ to join private tennis clubs etc, it's not uncommon to see some of the sherlock homes clothing style.

I admire his will to just go for it but he's taking a lot of this too far. There's some great touches but he puts too many of them in a single outfit. Less is more.

He also looks like some of his clothes don't fit too well. His Gucci coat up top for example looks a bit too big and a bit too long.

Either way...trying MUCH too hard. There are way better dressed dudes around.

Or the NYC socialite type.