To my eye, I would agree with 7a28

Vital to have the right tool for the job

In my mind this the quintessential watch. As simple as it gets by the brand who brought wristwatches to the masses.

"Also maybe holding off on a Rolex until i’ve earned one"

There's your answer. Give your rolex acquisition a special meaning and you'll love it all the more.

There's no substitute for what you want so if that's a rolex then the tudor won't cut it.

Watch of Theseus

Boring today perhaps as the watch world has diversified its designs; but they are classics for a reason. They (along with a few others) carried us into the modern Era and that's pretty cool.

Your examples have matured nicely, I'm envious

Absolute knockout. Heavy hitter in its own right