My brain gave him a cane at first glance too

I think I recognize the background. That's Churchill Downs. If I'm correct, I would also surmise that this was taken on Derby day. Which is all to say that he's actually rather conservatively dressed for the event.

He looks like Jim Carrey in The Mask after a kid need with the colors on the TV.

The Evil Sinatra look

Tom Brady, Walter Goggins, and James Spader walk into a bar...

I think I recognize the background. That's Churchill Downs. If I'm correct, I would also surmise that this was taken on Derby day. Which is all to say that he's actually rather conservatively dressed for the event.

Carol-anne, step into the light. fatha is here