Do we really want to get into a discussion of efficient market theory and price and labor theory?
But to answer your short question, the answer is yes. Price does equal quality (until what von Mise describe as "technology" is able to lower prices by cost saving manufacturing processes). But even then, when all other competitors adopt these cost saving manufacturing processes, all companies are once again at the same starting line in terms of cost and the higher quality company is still the most expensive. But you can still find deals if you behave like arbitrageurs and recognize that most companies incur the most cost from marketing and real estate (von Thunen anyone?)
Understand this and you can find very good deals for very high quality goods (many good tailors from Thailand and Hong Kong with very low overhead due to cheap real estate and labor costs in Thailand and Hong Kong make flights to the US to cater to US customers. A suit can go for as cheap as $400. Sure it isn't bespoke, but it is MTM and better than anything you can find at Nordstrom or even Neimman Marcus). A true bespoke suit from Hong Kong can be had for as cheap as $1,500 compared to beginning prices of $4,000 from the houses of Savile Row in Mayfair where real estate is the primary cost (you'd think the suit would be the primary cost of a suit, but you'd be wrong).
Another example, there are many watch companies that will use the same mechanism. However, a brand name that is very well known will require more money for a watch with "mechanism A" than a less known brand name with the same "mechanism A." Getting Tiger Woods to wear your watch makes your watch more expensive. And psychologically, Tiger's endorsement "adds value" to the watch. So Tiger Woods adds value to a watch literally (it is more expensive due to marketing cost) and figuratively (you think it is better). This is a situation where price = quality but only psychologically. But is psychological value still value? I would say no but only because I would know better. But to the person who loves TagHeuer because they see it in the Olympics or at golf tournaments, who cares? All the best things in life are the least well known.
As for the comment about watches lasting forever, even Mercedes break down. Watches, due to the miniaturization process, have very weak parts. These weak parts can't store a lot of potential energy. After years of grinding away, eventually, something gets stuck. A cheap watch will get stuck easier than one that has a quality mechanism. Even large, cheap, Chinese wall clocks that don't undergo the miniaturization process break down.
As for whether your watch is covered: only half your watch is covered and to the astute eye, will be seen. If you use hand gestures while speaking, the entire thing may be seen. But normally, half is concealed by your shirt (if the shirt fits correctly). Your watch shouldn't be flaunted or be a conversation piece. It is simply a sign of someone who respects time. Every time we had project meetings, the people who were always on time were those with watches. In a world where most men don't wear watches, it is always good to stand out. That is also why I am going with a simple white pocket square.
A good watch and well cared for shoes are not to be conversation pieces (I guess they could be). They are simply signs indicating other qualities.
As for the IWC being ugly, to each their own.
What is so "eco" about a sun-powered watch? So you're telling me there is current flowing through that watch? Automatics are still the paragon of good quality when it comes to watches.
Did you guys know that koala bears have fingerprints that are almost indistinguishable from that of humans?