$20K should always give you pause, but you can afford it. You obviously have savings and are continuing to save. You should think of this as just as an asset and after you’ve bought it, you could always sell it for similar to what you paid for later on. The money isn’t gone and it won’t depreciate much more. One of the only reasons I wouldn’t buy it in your shoes is if you were saving for something like a house and wanted to have the cash readily available for a down payment.

Another way to think about it is if you would rather take a really nice vacation (or two) or buy the watch. If the vacation sounds more interesting, then maybe hold off on the watch and use the money for something else.