Maybe, but boots for sure are better and cheaper than 100 years ago. I think the only thing that makes this slightly confusing is that what were old mass-produced workwear have become limited-run fashion items, so looking at things like M1918 boots or cowboy boots and comparing to modern Red Wings or Luccheses it's tempting to say "Oh how much more expensive leather-soled brass-hardware hand-tanned full-grain leather boots are now", ignoring that Modern soldiers wear lightweight goretex running shoe-boots and farmers wear cozy neoprene pull-ons with anti-slip soles and carbon fibre toes, both of which cost half of inflation-adjusted prices of the objectively inferior boots of 1925.
You're right that modern work and military boots are generally better for their specific purpose -- they are certainly much lighter and usually cheaper than their older equivalents. They can also be more ergonomic and breathable while still being water-resistant due to modern materials and processes. But I will say that the durability of leather, metal-hardware, stitched/nailed-sole boots is unmatched. They can be re-soled and repaired unlike (most of) their modern counterparts, and will last generations if properly cared for. And there are still jobs out there for which they are the best option.
