JC Penny for basic dress shirts and a few staples - good thrifting for the rest.
That depends on where one works.
It also does not cover weekend attire.
Respectable, but unremarkable. I've never heard a better description of a Rolex.
Regardless, I wouldn't wear one for dress. Certainly not with a suit. Regardless of popular opinion they're just too sporty, for my taste, to wear with actual dress clothes.
I thought "Overpriced POS that isn't remotely near waterproof or good looking as a dedicated dive watch" was the correct description.
Oh, be fair. Rolex has a long history, all the way back to its days as Unicorn, and holds more than a few patents on dive watch refinements. They're also well made, and a design classic.
And, since their move to in-house movements, they'd make a great $1500-2000 Swiss watch. Nice, and slightly above average. Genuinely a good watch.
But at their actual price, they're just massively overpriced, for what you get.
Patents are not an indicator of whether or not an invention works. A G-shock makes a better dive watch for the environment and money than any Rolex. Hell even a crappy Vostok makes a better dive watch.
I have a Vostok...and several Poljots, and a Raketa, and a Molnija. The domed crystal of my Vostok is designed to flex with increasing exterior pressure, and actually improve the seal. Amphibia series.
But the basics of the Vostok are remarkably similar to the innards of the in-house Rolex movement. It's actually a Swiss design that was sold to the USSR.
If you want to talk at this level, let's talk movement design, jeweling, lubricants, case design, and manufacturing tolerances, and finishing, both functional and cosmetic. And weak points as well, like the "wobble mount" of the Vostok crown on the stem, which has proven to be a decidedly weak point in their design.
Yes, I'm a huge fan of Russian watches...
The Air King - yes... but they do make good deep sea dive watches too.
I don't happen to like the technical dive watch look though - so, Omega/Rolex are good alternatives when found vintage (and thus more affordably).
Working men do not wear shirts and ties to work everyday, nor do they carry briefcases. This is more like the clothing a working man needs:
6x wifebeaters, not white because they don't stay white.
6x Navy coveralls, oil and grease stand out less on them.
Also 6X wool beanies. These are godsends.
I suppose it depends on how you define "working man."