I try my best to not judge others by how they spend their money so I am not really anti-anything whether it be BMW, Rolex, or Omega. For the record my wife and I have only owned 2 Subaru Outbacks in the past 20 years because we really do not fall into the car as status symbol thing; It is a tool to get us from point A to point B.
I own a Rolex because my father was gifted one by my mother when they got married and then another one for his 40th, my grandfather wore one, and my older brother got one from his wife for his 40th. As such, it is a family thing and not to impress others. I purchased my first Rolex when I received my first significant promotion and salary increase not that long after college. I got my second one from my wife for my 40th. I also bought a Submariner in the past few years but sold it because I did not really connect with it and noticed everyone had one which is not why I enjoy Rolex.
IWC is a wonderful brand with great history and they make fantastic watches. If you can find a pre-owned one (most people hang onto them) the Mark XVIII is a great all around watch that can span beach to boardroom. You are wise to start early so you do not feel pressured to get anything the appears to be a good deal but may not be since there are literally thousands of great pre-owned and new watches to choose from.
In the new and possibly under $2k category,
Oris is another great brand with history that has been making some really cool stuff lately. And it is hard not to love the
Sinn 104 which is a classic and well regarded amongst watch collectors but not really known to the general public.