Ferrari is exactly the same. You first have to buy a starter Ferrari or two in order to get invited to Ferrari events which in turn might get you an invitation to buy a limited edition Ferrari. Gatekeeping all the way down to maintain artificial scarcity. One might have wheels and the other keeps time (poorly) but they're the same and the scarcity is the product.
A beginner watch is a Seiko SKX (now the 5 line) at US$200, one can also do Hamilton field watches, Longines, Stowa, Nomos, Omega or IWC, etc for a few hundred to a few thousand.
Watch Youtubers like The Urban Gentry, Teddy Baldassarre, etc, cover (and own) watches from all sort of price levels (as do folks in /r/Watches, where you'll see state of the collection (SOTC) posts that have Casio G-shocks).
https://www.hodinkee.com/articles/casio-ae1200wh-1a-world-ti...
[0] https://www.highsnobiety.com/p/the-pope-tyler-the-creator-wa...
Nouveau riche are notorious for buying things that they can't really use the way they were built to be used, and often wouldn't know how to use them when given the opportunity.
That's the disdain being mentioned. It's not being snobby. It's recognizing people with fake status symbols.
If your story to be told is about stacking girls, then Mustang it is. That's being honest.
Of course a status symbol works to a large extent, otherwise people wouldn't be spending money on them.
I'm nowhere near the social circles of "old money", but I'd imagine they're more amused with seeing people trying too hard to push themselves into upper society, than being insecure about their own status. I mean, I don't have to be upper class to find this behavior somewhat comical.
But if having a rolex means you have some money but nothing to say... What type of watch do real watch people buy? And what interesting thing are they saying through their purchase?
The most prestigious brand is Patek Philippe. The nerds of wall street often wear IWCs. Blancpain, Panerai, Vacheron Constantin, and Breguet all have interesting offerings. The right Rolex (eg a yachtmaster for a passionate sailor) can also say something interesting.
The point is that your watch and its style and complications should ideally reflect what you value and want to show the world. This is kind of the same as car people at this point - there's no right answer, but there are some wrong ones.
Watches, cars, ties, and all other kinds of mens' fashion accessories are all the same, it's about communicating who you are through what you wear. Women know a lot about this because it's pretty much mandatory to adopt that attitude about women's clothing. High-end menswear is the same: if you're going to spend the money, spend it on something that fits you.
By the way, nobody who cares about watches will ding you (in terms of social status) for not wearing a watch or wearing a non-fashion watch like an apple watch or a swatch. If you're not into it, you don't have to partake.
https://www.youtube.com/watch?v=gy4tXbm-HN4
Insanely difficult to make well, barely two or three people in the world are capable, requires a high degree of understanding of various wood types to select for springs, regulation, temp and humidty correction, etc.
https://www.keepthetime.com/blog/valerii-danevych-wooden-wat...
What does it say?
Hard to tell - if I had one, for example, it wouldn't say much beyond I appreciate fine craftsmanship, woodwork, horology, and could afford to spend a quarter of a million on a unique piece of functional artisanship.
Personally I have no watches, chains, jewellry, etc - I'm a don't like things that can catch type of person - but I do like timekeeping and have a sapphire cclock for the precision.
https://spectrum.ieee.org/for-precision-the-sapphire-clock-o...
Otherwise, real watch people buy vintage watches. Universal (tricompax), Longines, Zenith (el primero), Heuer (not TAG Heuer), Minerva (Cal. 48), Omega... And like with old cars, a real watch person accept a degree a quirkyness: less accurate time keeping (but honestly it's not that bad), manual winding every morning, a blemished dial and scruffed case, finding and befriending a watchmaker with the right skills to maintain it every 3-4 years...
It's part of the charm.
Like with cars, the current batch of watches - on top of being luxury items, when in the past it tended much more towards practicality and "toolness" - doens't have the same flair, style, history or fun.
At the end of the day what matters to 'real watch people' is that you are interested in and passionate about the watch you are wearing. If you can talk about the watch you are wearing and what makes it cool and why you love it, then people will think it's cool
Their magazine contained a review for a $26,000 decorative rock for your patio. Not a fancy sculpture, just a rock.
I wouldn't take anything they say seriously.