Peers, getting into luxury watches now. Rolex has already been a dream and gravitating towards Submariner Date. Is this a good choice or would you suggest an alternate brand ?

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Have two subs. Amazing watch but buy for personal enjoyment and not for investment ROI.

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It's the most iconic watch of all time, so you can't really go wrong there.
I personally prefer the date and like the cyclops, but it seems I am often outnumbered on that count.

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What other Rolex watches attract you?

I mean, you can always get a Sub Date, buy it gray for an extra $2k, and look like every other person who wants a Rolex. Don’t get me wrong, the Sub Date is iconic and amazing, but it’s just so ubiquitous.

It’ll almost certainly hold its value and it’ll last a lifetime, it just usually says, “I have money and want to buy a Rolex because it says Rolex and everyone will recognize it’s a Rolex”. There’s nothing wrong with that, but just know that a Sub Date on a stranger’s wrist gets respect from everyone except “watch guys”.

It’s a safe choice, it’s just not a smart choice (since they can’t be found for retail), nor a creative choice.

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If the entire premise behind buying watches is for you, M1’s point seems invalid. Don’t buy a watch because someone else will notice it nor because someone will judge you for having the same watch as everyone else.
@OP: if this is your dream watch and this is what you’ve always wanted. Go for it. My only thing is to not buy it from gray especially if this is your first luxury watch.

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OP, is this your first automatic watch? Before dropping $10k on a Rolex, why don't you try out something far cheaper to see if it's really the sort of thing you like, and also what you like.
If divers like the sub are your thing, you can get an SKX007, Orient Mako, or one of a ton of cool microbrands. Jumping from nothing to a luxury watch is not what I'd recommend.

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I’ve had a good experience with DavidSW. Depending on the model you might be able to negotiate a bit of a discount.

The best advice I can give you is to try a bunch of stuff on - you never know how a watch will feel/look on your wrist vs on a screen. Maybe even start with something more affordable before you jump up to a 5 figure ($) luxury piece. The Submariner you thought of initially and the DJ that M1 recommended are both great choices, but I’d add another dimension to the criteria questions, which is where you plan to wear it.

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It was my first luxury watch (sub no date) and it’s a solid everyday watch. Not regretted it ever

Thanks D1.. Is it considered a good investment? Also, planning to get from gray market.. Any recommendation on Year and website for it?

Eh. I didn’t get it for investment purposes. I’d be lying that if the fact that Rolex holds up well in terms of its value isn’t an added bonus. I doubt I’d ever sell this particular piece. I got it from an AD and didn’t go gray market

Thank you , M1. As you know by now that I am a rookie in this. Can you recommend a watch for a rookie like myself who can get respect from strangers and watch experts alike as well as personal satisfaction. This is for a milestone occasion and will hold a special memory .

For reference, I recently bought a 36mm DJ and I absolutely love it. I have lots of watches in the collection and there’s a reason this thing has been beloved for nearly a century. I got the previous generation because I wanted some specific features, but the new version is equivalently awesome. So comfy, so timeless, and the perfect introduction to high horology for a newbie.

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Thank you, EY1. Any grey market sites that you recommend!

Can't go wrong with a Sub Date, especially if that's your dream watch. Getting any SS sports model through a Rolex AD has become quite the ordeal though these days. On the other hand, if you're not deterred by this or open to a gray market purchase, I'd say go for it!

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Was just offered this by my AD. If I take it will my chances of getting a sub or GMT go up or down? EDIT adding context:
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