The second man has serious style, and his outfit could be tailored to a heavier man. However, if you're not a young, handsome guy who pays so much attention to your hairstyle that people will notice it before your epic static cling, you can't get away with the first man's look.
I don't think the first guy gets away with the first guy's look, it looks terrible. The trousers are a ghastly colour, texture and shape, the jumper is a different yet still unpleasant colour and a poor fit, the jacket is a nice jacket but a terrible fit, the socks are ugly and the boots don't go with the rest of it. That he is pictured in a sartorial blog is everything that makes me think fashionistas are making it up as they go along while laughing to themselves and pocketing stacks of cash into the bargain.
It doesn't go together, it doesn't fit, it doesn't look expensive and showy, it's not crowing designer labels, it's not bold and contrasty and awesome, the only redeeming feature it has is that he's obviously put effort into making himself look so unusual. And that's fine, he wins points simply for doing that instead of wearing jeans and a t-shirt.
Compare this young guy: http://www.thesartorialist.com/photos/12010TanLeather3822Web...
with this older man: http://www.thesartorialist.com/photos/11810DGscarf3456Web.jp...
The second man has serious style, and his outfit could be tailored to a heavier man. However, if you're not a young, handsome guy who pays so much attention to your hairstyle that people will notice it before your epic static cling, you can't get away with the first man's look.