Question from Beginner

I'm a lawyer by profession and became a certified sommelier in my "spare" time. When it comes to wine, I'm always telling people to drink what they like, labels be damned. But I'm a snob (as are many somms), and I secretly judge people who rave about certain wines, especially the "famous" ones that are ridiculously overpriced (and quite frankly, not that good). Today, I cringe when I think about what I thought was good as a wine newbie.

Is it the same for watches? For those "in the know," are there watches that are considered gauche/tacky? Genuinely curious. Not sure what my first purchase will be but doing my research on Rolexes and a few others and checking out a few ADs in my area.