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MichaelVassar 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.
Shoes that are comfortable but are not sneakers cost about $400 but DAMN are they worth it if you have to wear shoes. In men's fashion in general, uncomfortable imitations of elite clothes are favored by the North Eastern middle class, who don't realize that by spending 5x as much they wouldn't be so miserable, and don't have the confidence of the Western middle class to rebel and wear sneakers.
There's an implied, but not necessary contradiction there. Maybe the middle class doesn't shell out for expensive shoes because they've tried and gotten uncomfortable ones. Or maybe it's easy to find comfortable shoes, so long as they aren't Italian. But that leaves the question of what's wrong with the Italian ones.