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Piling on, but love it
My god, man, he can't even afford socks and you're telling him to buy a wristwatch?
But seriously. No socks with unlined shoes? Fine. Sockless in real shoes? The 2012 version of the mullet.
I think there can be a certain good humour in wearing a digital watch with a casual but tailored look. I think to get away with it, it's best to go really, really retro, something like the Casio F-91W. The G-shock doesn't come across as deliberate enough to me.
(I also think socks would help, and non-black shoes unless that tie & square are also black; I can't tell from the photo).