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There are many watches between an entry level mechanical and a Rolex. I wouldn’t buy the cheapest one you can, and I wouldn’t jump straight to Rolex at first, either.
Start by thinking about the type of watch you want - sports watch, dress watch, everyday piece, etc., along with the type of movement you want. Mechanical watches start as low as ~80 for a Seiko 5, and get astronomically more expensive as you add complications, quality of components, and quality of finishing. Seiko is a good brand that has options at price points from $80 to $8,000+. Outside of Asia, brands in the $300-3000 range will use off the shelf movements from ETA or Sellita - these are regarded as high quality movements that are inexpensive to service. Above the ~$3000 point, you start to see in-house movements from brands like Tudor. These command a little more respect from enthusiasts, and in some cases can offer design advantages over ETA/Sellita (complications, shock protection, power reserve, etc.). They are more expensive to purchase and service but generally higher regarded. On the movement front, keep an eye out for movements that are marketed as in-house, but are just manufacture-assembled ETAs. This is acceptable in the <$2000 range, but becomes harder to justify as price increases. Loads of brands do it - Hamilton will sell it’s own ETA 2824 in a $600 watch, and Tag will do the same in a $2500 watch - tough to justify the extra cash. This helps justify prices from brands like Rolex - their movements are very reliable and you can’t get a Rolex movement from anywhere else. Personally, I’d recommend avoiding the $1700-3000 range due to the value proposition in that area.
Be sure to consider the case size - watches are trending smaller these days, but there are lots of huge watches out there. I’d recommend staying at or under 40mm in diameter (42mm if you have a large wrist). Thickness is a factor as well - 15mm is tough to wiggle under a dress shirt cuff in the office. Trying on watches is always helpful if you can swing it, even if only to get a feel for sizing.
There have been a number of recommendations in the past week or two - have a read through the posts in the bowl. Happy to answer questions! Welcome!
Only thing I would add OP is that true watch enthusiasts won’t judge you on the price point of your watch, they’ll see the watch you chose based on your price point. Purchasing a watch that’s sub-10K but has a good brand and strong movement still carries a lot of respect amongst watch-lovers.
think about this too - if you are on a staff reduction engagement are you going to strut in there flashing a Rolly or would it be more prudent to wear something a little more subdued? it might make sense to get an inexpensive watch because you get the benefit of wearing it now and it might serve you in the future.
Obviously depends on your budget but most would advise to save and wait. I hate all the cheap watches I bought before my Rolex
A2 knocks it out of the park. Hodinkee.com is a good place to start geeking out about watches. I started reading it when I was researching my first watch, got really into Soviet watches and now I have a very cool vintage Raketa with an interesting world-time function that starts a conversation with every watch person I meet.
Buying cheap watches is expensive in the long run. Figure out what you want and save for it
Better worded than what I wrote. Agree with you a2
I think it’s worth saving up for a Rolex, although in today’s market, it might be hard to actually get a steel model. Or you can get a Nomos for around $2K. Now that’s a quality esoteric piece that can last awhile while you save for other higher end pieces