Having seen this thread develop, it seems to me that Panerai, Breitling, Hublot and Audemars Piguet (particularly ROO) are the most divisive brands.
They have as many devotees as adversaries.
In general there's not a lot of love here for extravagant and conspicuous watches like Richard Mille, U-boat, Bell & Ross or Jacob & Co.
I myself like only a few watches and I tend to go by design rather than just horological pedigree.
My other "rule" is that it should be a watch that I can reasonably afford in real life.
The Calatrava and the Nautilus are truly gorgeous watches I think, but financially off limits to me.
Most Rolex models are in that same category, but frankly I would never buy one, even if I could afford them.
I know many here are big Rolex fans, so what I am about to write may be like having a dump on the church floor.
Firstly, they are so ubiquitous and recognizable that they have become a cliché.
I quite like the Submariner for its classic design and all, but it is mostly worn by folk who could never ever afford to buy a genuine one (here in The Netherlands anyway).
Wearing any one Rolex model you're bound to be asked "is it real?", even by people who know bugger all about watches.
It's a bit like those Canada Goose coats, you just know that 99% of the ones you see are fake.
Secondly, and more a matter of personal taste, I think most current Rolex design is really rather boring and parochial, if not outright ugly.
They have revolting colour schemes and hideous two tone- and gold models, Bluesy's, Hulks or whatever they're called; I find them very unpleasing to the eyes.
I think Tudor, as far as design goes, has the upper hand on its bigger brother.