To answer a few of your questions: 1. In my opinion the preppy look consists of the following: shirt: polo shirts (often with a lacoste/polo logo) and rugby shirts, often with bold colors or horizontal stripes and sometimes worn with collar upturned; button-down sport-shirts, usually in a white or pastel shade. pants: either shorts or chinos, almost always in khaki or white, though the more "adventurous" sometimes wear pale blue, nantucket red, yellow, or plaid, although they usually offset this with a white shirt. shoes: boating shoes, penny loafers, or sandals accessories: woven leather or colored canvas belt, sweater in similar colors/styles as polo shirts. I don't think its necessarily a bad look, but it can get tired pretty fast. It also tends to draw ire from a lot of people, see point 4 as to why. 2. As for baggy clothes; in America, the average person either tends to be rather overweight or bulky and muscular. To accomodate that market, clothiers have to make their clothes looser and cut them larger. It's feasible to take in a few inches on a suit or cut away some extra fabric and make a too-big garment look acceptable on a smaller person, but it's not possible to add extra material to something that's too small, so it makes more economic sense to cut clothes larger. Americans also are concerned heavily with comfort, and to some, form-fitting clothes can be perceived as confining and unnecessary. I don't think your average American would mock a Dior-type look; rather he'd say something like "why bother?" 3. I really hate the beige look too; my guess is just that it's just a non-offensive "color" that saves the average man the effort of coordinating a wardrobe. I see black a lot in the cities though, actually to the point where I think it's being overdone. 4. My take is that a lot of American guys hate fashion because they see it as pretentious and elitist (they have somewhat of a point, a visit to any major label's website will show you how full of themselves some designers can be). The general opinion is that since decent clothes (and Banana Republic et al, isn't necessarily bad clothes, just boring) can be had on the mass market cheaply and easily, there's no reason to spend a lot on clothes. Take a look at how Americans dress for interviews in such a bland manner. If you show up in a slim-cut three piece suit wearing a pocket square and french cuff shirt, a lot of people will get offended and think you're some kind of ostentatious prick. One possible explanation for this trend is that fine clothes have always been associated with wealth, and give off an aristocratic image. America has never taken kindly to the idea of nobility or aristocracy, and basically was founded as an agrarian/blue-collar protest to the European tradition. I think that legacy might have something to do with the poor perception of fashion in the U.S.