My most expensive watch is about $500 I bought several years ago. I have about 7 that I have accumulated over the years. The one I wear most often is a $20 timex I got at Walmart 3 years ago. I wear it to work as I have broken/lost too many watches to risk it anymore. I had a wealthy brother in law that was the epitomy of fashion. He was showing me a watch one time that cost him about $25K. I of course didn't recognize the name because I'm not into the status symbol stuff all that much and he was disappointed. He said he got that reaction from almost everyone, so he traded it in on a Rolex because most people knew that one.. This was a few years ago when Rolex was king.
I understand Coach wanting to buy something like that as a long lasting gift to himself. I wouldn't spend that much on a watch, but I've spent money on custom paint jobs, or classic cars that other people thought was a waste of money.. to each his own.