re: Best watch $1,500-$2,000

Don't get one for that much

Here you go:
Reactor Watches

Once you get above $1,000 or so you are buying the watch more for the name than anything else because you can get a great Seiko watch that keeps time and never breaks for $200.

There are good, Swiss made mechanical watches in your range. The problem is that most people won't know the name unless they are really interested in watches. I think Tag Heuer and Longines are going to be your best match in terms of quality and name recognition in your range. Personally, I like the classic look of most of the Longines watches. And it's a known Swiss brand that has been around forever. Even the non-watch aficionado will likely have heard of Longines. If you are looking for a more modern design, then Tag is probably more your style. Another brand I like is Frederique Constant. It's a Swiss brand and their watches are relatively affordable. The brand hasn't been around that long (less than 50 years), but IMO they really make some beautiful classic looking dress watches.

You're almost assuredly not getting well known brands such as Omega or Rolex in that price range.

The OP didn't mention a particular style which makes recommendations more difficult.

Some people are also talking about grey market pricing and most people giving a watch as a gift want to buy from an AD (authorized dealer).

There are quite a few watches in this price range and the one that calls out to me most is Nomos but to a degree it is a watch guys brand just like Grand Seiko but a Nomos would probably be my choice, a lot of watch for the price. Sinn, Longines, Oris, Ball, Baume & Mercier, Rado, Bell & Ross, Eterna, Ebel, Victorinox, and Tissot are just a few of the brands that will have solid watches in the range.

I think you get the most watch from Nomos, but Sinn, Ball and Oris are also value leaders in the price range.

I would avoid Tag OP. I like most of the other watches listed including Stowa, Fortis, Sinn, Longines, nomos, Breitling, and Omega. You can't go wrong with any of those. If it was my money I would pick up a used Omega or Breitling which should be enough money to get within your parameters.

I bought a new watch yesterday, Broke.

Had to order it. It'll be here tomorrow.

LINK

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A lot of people hate the DSSD due to thickness and diameter

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I bought it because of those two things.

RGM is a great american made brand. My RGM 250-P is about 3K.

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I bought it because of those two things.

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I don't mind chunky dive watches, I also have 2 Panerai 44mm Submersibles and 2 Omega Ploprofs which are even chunkier. The DSSD has simply the best dive bracelet on the market and the one all others should be judged by. Rolex went from the worst bracelets to the best in a pretty short time.