HughRistik comments on Why Real Men Wear Pink - Less Wrong
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In general, T-shirts aren't optimally fashionable in terms of high fashion, but they can be fine for normal cool guy fashion when done right. Graphic print T-shirts are great for the day, usually accessorized with a necklace, watch, or wristbands. They need to be reasonably tight, because a baggy look evokes high school and fails to show of your shoulders. At night, T-shirts are great fine for most clubbing when worn under a blazer, jacket, or sportcoat.
While I find this hypothesis completely plausible, I do think that a lot of these uncomfortable items are simply aesthetically superior. Pointy-shoes just look more elegant to me, and I don't think this is because they are uncomfortable.