1 - Timex Ironman
2 - Old-school G-shock
3 - Quartz Pocket watch, faux gold plated.
... I jest.
So much personal choice here, so, I'm going generic.
A nice dress watch.
A tool watch (think diver, g-shock, ironman)
A fun watch of your choosing. I like Vostok for price and modding is super easy.