If you have a weekend home at the Hamptons and you plan on a boat trip, by all means wear them. Seriously, they would look fine with a pair of rugged jeans and a polo shirt- for that outdoors look.
Nearly everyone in my city wears them (crappy little student's city!!!). Actually I kind of like them. I've got two pairs (the "real" ones and the ones with the flat sole). But I only wear them while walking my dog. For me they're just functional and NO fashion statement. So you would never catch me dead wearing them while walking around in the city... When it's raining I wear rubber boots and if it's not raining I wear Timberlands...
I love this eastcoast "preppy" outdoor style - but only when I'm outdoors. So no topsiders, longchamp bags and barbour jackets for me on the streets
I don't think that there actually exist something what is really called that way and I also don't think that someone living at the eastcoast actually dresses that way... well maybe!
But for me this style is one which a lot of people associate with the eastcoast or the WASP-style (White-Anglo-Saxon-Protestant) or just "preppy" something inspired from the british aristocracy.
Those people mostly wear brands like timberland, barbour, burberry (in europe male and female), longchamp, tod's... there're some different brands in the US. http://en.wikipedia.org/wiki/Preppy Wikipedia is quite helpful.
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