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jkaufman comments on Procedural Knowledge Gaps - Less Wrong
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I still have not figured out how to find work shirts that won't ballon when tucked in. I may be smaller than most people who give their clothes to the thrift store, or it may be there's something about this I don't understand.
Most shirts are "classic fit" or something along those lines. Well fitting shirts for slim people are "fitted" or "slim fit" or some such. "modern" is usually in between. The same goes for tshirts and pants. http://www.primermagazine.com/2011/field-manual/how-to-wear-a-tucked-in-shirt-without-looking-like-an-old-man
You can also get a tailor to slim your shirts. This runs about 30 USD/shirt at a tailor shop but sometimes you can find people offering such services on craigslist for less.
shirt stays
They will change your life.
That is an excellent concept: reverse suspenders.
I go barefoot a lot, including walking to work, so I'd need to figure something out with that. Possibly just putting on the shirt stays when I put on my shoes, socks, and dress shirt at work.
You can wear shirt stays while walking barefoot if you leave the bottom disengaged, because the elastic pulls them up into your pantlegs. Also, there are different types. Some clip to your socks like they do to your shirt; some loop around the bottom of your foot. The latter type would be possible to wear completely engaged while (aside from that) barefoot, if you really wanted to. They also have the advantage of not leaving deep, red, itchy, clasp-shaped impressions in your ankles.