I've been considering my WIS journey of late and found this article quite thought provoking:
http://www.ablogtowatch.com/point-co...st-nice-watch/
Some of the comments in the 'IWC vs Rolex' thread are also in a similar vein ("I'm just like anybody else: I want to be a nonconformist too)."
Personally I started out with some 'avant grade' choices such as a Christian van der Klaaw and a copper dial Sinn 356 but eventually decided to move them both on. More recently I tried a steel sports Rolex for a short while and it just didn't feel right for me. My Grand Seiko quartz could be considered conservative but it has subtle design features (such as the razor sharp hands) that just make it 'pop' for me. My latest purchase will be a Sinn 556i (with the sunburst anthracite dial). I seem to be returning to more restrained/classic versions of the watches that I was originally drawn to.
I guess that so long as the choices we make truly reflect our tastes then either path is valid?