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BTW, this whole idea that men have to wear suits or sport coats is BS. I don't get how some people wear a suit to work every day. I'd go crazy.

How did society ever develop this idea that "looking good" means "being uncomfortable"?

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@CarlCravens
The same way aristocrats wore big rings and unpractical clothing: to show that they were not doing manual labor.

@federico3 @CarlCravens The issue with this explanation is that decades ago people from any part of society were wearing the kind of clothing that today we associate with being uncomfortable (at different levels of quality and/or number of previous owners), even while doing manual work.

One hypothesis I have is that as things became something “special”, not worn every day, a number of things happened which includes them being made in a way that was cheaper, but less confortable, plus people are less used to them and thus no longer know how to buy them in the right size (if it was available, of course, see above) and are thus wearing things that are unconfortably badly fitting, and possibly other factors.

I suspect that at least some of the people who wear these things every day spend more on them to get them fitted properly, and are thus not so unconfortable.

Also, when in doubt, I would blame syntetic fibers. No really. Say not to those. (unless possibly in technical clothing where they are used to make things thermoregulate rather than just for the looks)
@valhalla @federico3 @CarlCravens the main reason is ''industry''. Just one century ago , if you needed clothes, you went to an artisan , or one woman in your family/big family capable to saw. The first thing this artisan would have done was to take your size, very very carefully.

If you buy a suit today you may chose ,like, 4/5 nembers to describe your body. When an artisan does your suit, it will take two measure for arm length, arm sizes, shoulder size, chest size, belly size and hips size. On legs , it would be your gluteus size, thickness of legs, length to the knee, knee-feet. You have no chance with industrial products to do this, unless you buy your suit from a high class atelier.

Same was for shoes.

Industrial ''casual'' products are fitting because the sport design is lousy and the look is very tolerant. But you cannot do it with pre-industrial design. This needs to fit your body pretty well.
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