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I was unaware anyone thought preppy was a good thing since the early 80s...
I doubt that it was ever a good thing.
Prep is all about exclusivity and class warfare. It is "us" over here with this exclusive fashion that we use to signify that we are part of this exclusive club against "those" over there that are not. At the time Ivy League schools were exclusive and did not accept everyone in. People were paying cash to go to those schools and this was before financial aid opened it up to regular people with exceptional grades. The prep look was an indicator of pedigree, not just wealth.
People often confuse designer clothing, which takes elements of prep, and confuse it with what people in the scene actually wear, or in the case of the early eighties, what they wore. Yes there are aspects of Ralph Lauren, Polo in particular, Tommy Hilfiger, and Nautica that have that prep ethos. But they aren't "prep" in the classic sense in that they add and subtract from the look, which was narrowly defined in the seventies and eighties. Anyone that was truly in that scene wore clothing that cost far more and brands that were not as well known outside of that circle. Prep was never anything that ever needed to be advertised or commercialized. The closest thing to prep, so far as designer clothing, might be Brooks Brothers as it was the genesis for Ralph Lauren's earliest collections. They don't change and they do not chase the trends. You thought they would have after Ralph Lauren became wildly successful but that did not phase them.
Saying that those brands are prep is like saying that Marc Jacobs was grunge.
There is also an aspect where people want something to be prep, because they want to know that their closet meets the standard. But the truth of the matter is that prep is more anti-fashion than it is anything people really want to wear. It is more about communicating a message or an idea, than it is looking good. All of the brands considered thus far in the thread are just exploiting the idea of prep as a foundation to build their own looks upon, but falling short of truly going there as to not alienate their urban market.
Some of the clothing they make could definitely be considered preppy. It is dependent upon how and where you wear it. In many situations a preppy casual look could be acquired by wearing these three brands.
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