radicaldog
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This is true of 99% of menswear, including things on the CM side of the board. Nearly all of menswear derives from work, sport, and war. The Norwegian split toe was originally a work shoe worn by British railway engineers, and yet people here pay thousands of dollars for them. Peacoats and chinos were military garments. The penny loafer has its roots in fishing shoes.
This sometimes makes me think that we--fashion-minded folks--are behind the curve. It seems as though in order to dress well in simple, practical clothes one has to go to great lengths and great expense to find reproductions of vintage designs, or "takes" on those designs. I'm guilty of this all the time, with both bespoke CM and expensive denim and such. I often think I'm doing it wrong because of a lack of guts: perhaps to be "effortlessly cool" one just has to break norms like those who wore jeans outside of manual work contexts did in the 50s or so. Whereas most of what I wear is perfectly socially acceptable.
In that spirit, a hypothesis, for lack of a better word. I passed a building crew in the street the other day. They don't wear jeans to work. They wear dark synthetic (I think) trousers with many pockets--not quite cargo pants though, as the pockets aren't on the sides. They look tough as nails and very practical. Maybe one should experiment with that sort of thing. But see, I'm already overthinking this. I'm hopeless.
My spouse is an artist and she and people in her circles wear a lot of cheap vintage or random hand-me-down stuff, and often look very good in it. That's another way to do it, but again, it has to come organically from your circumstances. Basically I think the SF mindset can get you from bland business casual to interesting and well put together clothes, maybe even fairly stylish, but it can't make you particularly cool, except maybe if you reach some sort of Aufhebung whereby you also delete your SF account. Light at the end of the tunnel and all that.
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Edit: this sort of thing, which seems to be in the price range of cheap Wrangers and such.
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