I do get that the specific type I called out might have some functional equivalent that's simply a different style & material but is just as good, but not that cheap, they don't. Under $150, probably, sure. Under $50? No.
This suggests that the cost of clothing has inflated at more like 3x the nominal inflation rate, despite the existence of $18 (or cheaper!) shirts—the inflation was eaten up by worsening quality, rather than showing up in prices, but like for like, even with a generous "functional equivalent" accounting, the change was more like $0.79 -> $50+ than $0.79 -> ~$18—your "equivalent" dollar under the latter calculation in-fact buys less.
Your own example is an interesting one because a) it’s very hard to compare clothing by objective quality b) you’re changing the goal posts. I’ve found a carhart product that nearly exactly matches your specification and msrp’s for $40. I’ve seen discounters selling it for $25. Which is getting very close to your specific target.
My pet peeve is automated checkouts and ordering kiosks. These save stores and venues on labor costs by making the customers do the work for the store. For free, and disproportionally wasting customers' time.
(In many cases this applies to self-service in general.)
Based on what I’ve heard, it may be wasting time somewhere like Germany where the staff are scanning your items at lightning speed. However, here in Poland self-checkout is where you go to save time. Human-staffed checkouts are and have always been slow like an iceberg. Now and before self-checkout was ever a thing. I was relieved when they were introduced, precisely thanks to the time saved. I hate waiting in queues.
All self-checkout machines are moody and lock up if you so much as look at it funny. It would be somewhat acceptable if there was always a dedicated employee delegated solely to assist and unlock the machines, but stores cheap out even on that.
Now, you just need to deal with individual people being slow partially because it’s not their job and partially because it’s a lot less efficient to have a little kiosk vs a conveyer belt. Not to mention if you want to buy something that a store locks up you need to wait for them to go get it. Progress?