What can you tell about a person by looking at their watch / shoes / car? I guess very little, other than that they are willing to spend (or borrow) sufficient funds to acquire things. There are some things that we feel passionate about, and passion in one area does not equate to passion in another area. My guess is that if someone is sporting a five or six figure watch, they probably have the resources to spend in other areas as well. That doesn't seem to be a stretch

The comment above about the number of cheap watches one sees in boardrooms is really another way of saying the same thing. Great shoes, expensive shoes, run of the mill (or worse...) watch. What does that tell you? To me, all it says that the person "needs" to be educated about watches.
As for the poster who would profile customers by way of their shoes... foolish move. I was on the wrong end of such profiling when shopping for my annual calendar PP - admittedly, not a high end piece. I was really taken aback by the treatment I got from the sales guy that I walked out and bought the watch elsewhere. 4 hour drive vs 40 minutes. A trip I made in my Infiniti M35x, while wearing comfortable but inexpensive shoes.