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HughRistik comments on Why Real Men Wear Pink - Less Wrong
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Yeah, it sounded like you were looking for t-shirts, not fashionable clothing. T-shirts aren't fashionable unless you're in college. In high school, they signal that you take metal shop and smoke cigarettes. After college, they signal that you still live in your parents' basement.
(If you can't find the t-shirt you want on the internet, you're not looking hard enough.)
If you'd said digital watches or shoes, though, I'd agree. Damn, digital watches and shoes are ugly nowadays.
I'm more intrigued by the unwearability of some fancy clothing. Look at any Italian shoe costing over $400. You will find they are all unwearable: pointy toes shaped nothing like the human toe that trip you up; floppy sidewalls that make you look like you're wearing galoshes when you walk; painfully narrow yet overly long; polished leather soles that make walking on anything slicker than concrete impossible. Women's shoes are even worse. I think that making painful, difficult-to-wear clothing fashionable is a way of winnowing out people who aren't truly dedicated to fashion.
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.