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I always took it to mean that an individual was comfortable enough in his (or her) own skin to push the envelope and bend the sartorial rules and have a bit of fun in the process.
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I recently read Tom Wolfe's account of a New Yorker attending a summer cocktail party dominated by New England blue blazer types, written sometime in the 1970s...he described the gentlemen as almost uniformly clad in navy blazers and odd trousers in "go-to-hell" (his term) colors, such as lemon yellow, red, or (if I remember correctly) Madras.If I'm not mistaken, the phrase was coined by the writer Tom Wolfe. FWIW, I also believe that the OPH "definition" of GTH clothing (specifically pants) is the first thing that comes to mind when I hear the term. Lilly Pullitzer pants, for example, are an obvious example of something that falls into this category.