What you've hit on is what anthropologists designate as the difference between vernacular and academic design. One of the things that our culture has lost along with the "skill" of garment sewing, is the comfort level that allows everyday people to just... mess around with fabric. (There's a whole 'nother braindump in there about Burning Man, but that's different.) Instead, we trust the taste of professionals, and so mainstream fashions become as stilted and identical as they have been lately.
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Argh, I think I need to go write an essay now.