I have a number of nice watches each representing something special in my life. My dad got a watch that he still wears from his 21st. I asked for the same on my 21st. I still have it and wear it
When I got engaged I asked my wife to buy me an engagement watch as she had an engagement ring.
There are a few more, but the point is the watches represents something personal and not about showing off.
In buying the watches, I have found that buying them duty free is by far the best for getting a good deal specifically when going through Hong Kong or Singapore. Being a traveller, the salesperson will give a cheaper deal as you are only passing through.