[Go-to-hell clothing --- For this, it was very important I find a picture of someone wearing Madras (or, really, any Ivy League style of go-to-hell fashion) absolutely seriously, in its original context. This was very hard to do. The best I could come up with was this Rhode Island guy above, or Madmen's Pete Cambell, who is a serious actor in a show that attempts to seriously recreate the 1960s, playing a character that would seriously wear Madras (below). You see, now that it has become adopted by world-wide fashion, most pictures of people in Madras are either wearing it somewhat ironically, or wearing it as if it were merely a "wild card" fashion choice, or wearing it as an general appreciator of Prep fashion, or perhaps simply wearing it trendily. But all of these are not what Madras was really about the first time it was worn and adopted.
The Go-to-Hell article of clothing, most famously characterized by the Madras pattern, was an upper-class WASP invention that really began flourishing in the 1960s. Men who wore conservative business fashion throughout the week would spend their weekends dressed in also conservative Ivy fashion, except perhaps with the addition of bright Red pants (Nantucket Reds), or Madras coats, or something with a pattern of animals stitched on it --- items of clothing that author Tom Wolfe coined as having a "go-to-hell" air. And indeed, to clash so loudly, and alongside such a conservative non-clashing of colors and patterns, was a way of saying something much more complex than "Aren't these pants fun!?!"
Yes, it was soon adopted as a uniform, and quickly became yet another esoteric fashion language shared by the New England elite and other rich WASP families. (As Wolfe further put it: "The pants were their note of Haitian abandon… at the same time the jackets and ties showed they had not forgotten for a moment where the power came from.") But it was still saying something that is a natural part of human nature, especially the independent nature of Americans.
There is a strange thing that sometimes happens regarding irony. Things worn first for the sake of irony soon begin to be worn in all seriousness. Comedy musician Tim Minchin experienced this with skinny jeans --- first, he wore them as part of his over-the-top rock star alternative-ego. However, he soon realized he actually really enjoyed wearing them, and what it meant to wear them. Similarly, one today might start wearing madras ironically, but might soon actually really enjoy wearing them. What they being to enjoy about them, I think, is the go-to-hell attitude inherent in the pants.
Many people spend a great deal of time in their lives --- and in their fashion --- trying to not be ridiculed, or embarrassed. Especially in those areas of life where they are expected to conform to a certain code. If someone says "go to hell" with their fashion choice, they are saying, in a sense "I don't care what you think. I'm dressing the way I want to. And that makes me happy." It's very empowering, and that's a good feeling to have, even though the wearer of such a thing will have to stand up to, or ignore, ridicule.
(Though, note: Now, as modern culture has now made Prep go-to-hell fashion the norm, and you grab some madras pants, you're no longer really saying "go to hell." You might be saying "I enjoy prep fashion," which is perfectly fine, or, "These pants are symbolic of a go-to-hell attitude in fashion which I wish to honor by wearing them," which we here certainly appreciate, but again, not exactly "go to hell.")
Overall, modern sartorialists should learn what a real, true go-to-hell article of clothing means both in fashion and in life. We fashion-lovers spend so much time trying to make sure the patterns layer properly, the colors work well with each other, that it's not wrinkled --- all extremely important aspects to the art of dressing well. But I think that sometimes we forget we're allowed to dress the way we want, for ourselves and ourselves alone. How do we do so, without relying on the already mainstream examples of sartorially-admired, classic go-to-hell fashion? That's for each man to decide for himself, as was done by the first New England WASP who said, fuck it, I'm going to wear this blazer with bright red pants.
Because, even though doing so can be in defiance of many people's ideas of good dressing, saying "go to hell" with something in an outfit can sometimes be the difference between a good dresser and an exceptional one.