There was an episode of the Bob Newhart Show (the one with Suzanne Pleshette as his wife) where she bought him a $10,000 watch. His response was "if you were going to spend that much money and after buying a piano, ypou had $20 left over and bought me a watch..... Well, you can't buy a $20 piano".
Similar to my belief that while it is seldom a wise investment, everyone should own at least one new car in his or her lifetime, if somneone wants to own a higher quality watch (and it makes economic sense), he or she should do it.
I own quite a few reasonably good watches (nearly 20, cost anywhere between $300 and $650 , accululated the collection over a few decades), but for more than a yer (due to the benefit through my health insurance of having a watch that counts my steps) use almost exclusively the least expensive watch in my collection.
I can speak of the benefits of the watches that retail for less than $1,000 but at this point I could also make an argument that it would have been better served owning fewer watches at a similar cumulative cost as better watches do hold their value.
Take your time making the decision. Whether it ends up being a good or bad decision will depend on the time after the purchase, not necessarily the purchase itself.
