I pined for a Rolex for many years, seeing many of my bosses wearing them and loving their prestige, history, and timeless style.I got myself a Bi-metal Oyster in 2004 and LOVED it.
Then I wanted a President and finally got one. Again, LOVED it. All for my pleasure and certainly not to impress anybody else.These days I have many CWs and thoroughly enjoy wearing a plethora of a mixture of watches, rather than always wearing the same watch. I don't think I could ever return to just owning ONE watch. It just doesn't make sense any longer. My mood changes often, often more than once a day. Many watches for many moods, seasons, events, weather etc etc and never a fear of being mugged.
Wear what suits the mood, your style, and your wishes.
Just be careful not to flash the kind of watch w*nkers are happy to relieve you of.
A SAD state of affairs, but there will always be envious/jealous people around. Enjoy wearing a Roley, but be conscious of your company/idiots around you