The French guy earlier did it pretty convincingly, but not Pitt. It is definitely a look that people even beyond the forum love to hate. If you are a bit of a show-off anyway, then I don't see why not. I think wearing the ascot actually helps. So, perhaps if you aren't already comfortable wearing an ascot, this would be risky.
That said, the contrarian in me wants to support it. The hatred in this case is so predictable that it almost makes me want to wear my collar out and so long that it ends somewhere around the knee. So bored of Clooney and the praise of him.