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As a society we’ve figured out that dressing up is generally wearing uncomfortable clothes for no good reason, so we stopped

I wore a suit for years until the company I work for asked me not to.

When I was younger, I found them uncomfortable.

When I was in my late 20s, I started going to a good tailor and purchasing fitted shirts of 100% good quality cotten, suits of wool with no synthetics, and comfortable, quality shoes and it made all the difference. The only time I found suits uncomfortable after that was when wearing a year-round suit outside in the hottest days of summer, but even that can be mitigated with a summer-weight suit. If it were an option at my employer, I'd wear a suit every day.

I had to figure it out for myself, and it took a few years, but I found the additional cost to be minimal, but the difference in comfort to be almost profound. It's really a question of knowing how to shop for clothing.

But it's rare to find someone, even within the clothing industry, who knows what works. If you can find an older tailor and get his advice, it's minimal money well spent.

I’d never wear it. Part of it is regional, here in Tucson if you wear a suit and you’re not in the finance or funeral industries people think it’s weird. Part of it is just me. I’ve had good suits for weddings and yeah they were actually more comfortable than one would expect, but they’ll never be as comfortable as pants and a shirt, and of course there’s the noose. Never liked ties, it’s just a slipknot around the neck that falls in your food to me.

A long time ago Tom Wolfe wrote a brilliant article about the rise of Intel. A big part of that article was discussing the culture clash between two guys who grew up in farm country and went to CA and never wore suits or ties trying to scare up venture capital from New York financiers who’d never dealt with people not in suits before. At the time I first read that article I worked for a software startup and we interacted with investors all the time, and other than their much nicer shoes and watches they dressed like us. They didn’t need to impress anybody anymore, and we were used to impressing people with our brains not our clothes. Now I work on hundred million dollar software in comfortable pants and a t-shirt, clothes don’t make me more or less capable of doing my job.