It honestly depends on your 'style' and what kind of look you are going for, and when you would be wearing them. In my honest opinion, I would prefer to see my man or even friend in a pair of DC's, Circa's, Puma's, Nike's or something along those lines. Comfortable & trendy. I do respect a sharp man though, with dress shoes and such, but it honestly depends on what else he is bringing to the table, and under what circumstances. Hope that helped. Good luck, but honestly be comfortable wearing whatever YOU like.
I vote buy. They're sexy, suave, beautiful, delicious, and any other synonyms you can think of for "pure sex appeal". More guys should be wearing Oxfords like these (they're not wingtips, I'm afraid, but they're still gorgeous), in my opinion; love the broguing on the toecap.
It depends on your purpose. They're a very classy, traditional style of dress shoes, sure to complement a very snappy suit or tux (although brown wouldn't go with a black tux obviously). In terms of a modern, stylish look I doubt these will go well. Get them for their historically classy look, but make sure you only wear them with traditional outfits, not modern ones.
I would say definitely DON'T buy them. Go for a cap toe, square split toe, or loafers. I say stay away from too trendy, but a little style is good. Wingtips aren't fashionable; haven't been for a decade.