Rolex vs Tudor vs Omega: Which Watch Should You Buy First?

Hey {{first_name|Reader}}.

Back to watches for this week’s edition because I got really inspired to write this. A friend of mine threw this question out on X:

So find Daniel on X and give him a "thanks” because this was a blast to write, and took me several hours.

His question is the entire "first serious watch" dilemma in one tweet. You have real money on the line, you'd like to hand this thing down to your kids one day, and instead of clarity you get hit with fanboys, flex culture, and endless opinions.

This guide is for the guy in the $3K-$12K range who wants to actually wear his watch, not just baby it in a safe.

Most people choose between Rolex, Tudor, and Omega based on three things:

Here’s the cheat sheet:

That's the nutshell. The rest is just figuring out what kind of guy you actually are.

Rolex started life in 1905 as Wilsdorf & Davis in London, focused from the beginning on precise, reliable wristwatches at a time when pocket watches still ruled. A few years later the Rolex name appears; by 1919 the company moves to Geneva, Switzerland, and over the next decades it creates some of the most important "real world" innovations in watch history: the waterproof Oyster case in 1926 and the self-winding Perpetual rotor in 1931 are still the backbone of what the brand does today.

Culturally, Rolex is the default luxury watch. Everest expeditions, COMEX divers, airline pilots, CEOs, crypto bros, etc. For non-watch people, seeing a Rolex in the wild can feel like spotting a unicorn. For watch people, it's the brand almost everyone has an opinion about: some hate the flex culture and the wait list circus (me), others (also like me) admit they're fanboys while still making fun of it.

If you're brand new to this world and you say "Rolex," you're usually talking about one of these:

If you want to go deeper on the brand and individual references, Bob's Watches has solid primers on the brand's history and core models.

Rolex is not subtle about what it is. Whether you like that or not is a good clue for whether it should be your first big purchase.

Tudor was created by the same guy behind Rolex, Hans Wilsdorf. The idea, registered in 1926 and pushed seriously after World War II, was simple: take Rolex-level robustness, put it in slightly more accessible cases, and use more affordable movements so working professionals could beat on them without breaking the bank. For years, Tudor used Rolex-signed cases and bracelets with different dials and insides.

Today, Tudor has grown up into its own thing. It still lives in the Rolex ecosystem, still trades on the "tool watch for people who actually use their watches" identity, and still gets love from military and professional histories (think Tudor Submariners on French Navy wrists).

There's a running joke in the watch world that Tudor is just "vintage Rolex cosplay," and while some of the design language leans hard into that, but the reality is they make legitimately great, hard-use watches that you won't be scared to scratch.

If you're considering Tudor as a first watch, you're probably looking at:

Tudor's own "Inside Tudor" pages are great for the official history, and reviews from places like Fratello, Hodinkee, or Worn & Wound on the BB58 or Pelagos 39 will give you real-world impressions.

Tudor is the watch you buy when you love the Rolex idea but don't want to play the Rolex game, and when you want to actually bang your watch into door frames (or mailboxes for me) without needing to lie down afterward.

Omega's roots go back to 1848, when Louis Brandt started assembling pocket watches in La Chaux-de-Fonds. The "Omega" name comes from a breakthrough movement in 1894, and by the 20th century the brand was supplying watches to railways and militaries, timing the Olympics, and pushing precision in observatory trials.

Culturally, Omega wears a few hats at once. It's the Speedmaster, the watch NASA picked that ended up being the first watch worn on the moon in 1969. It's the Seamaster, tied to James Bond since the mid-90s. It's a longtime Olympic timekeeper.

For a lot of guys, Omega is "Rolex-level watchmaking without the unicorn hunt": modern movements with anti-magnetic tech and METAS certification, serious history, and the ability to buy the watch you actually want without begging an authorized dealer for the privilege.

If someone says "Omega," you're probably thinking:

Omega's official site lays out each line, and there's an ocean of deep-dive reviews from places like Fratello (especially on the Speedmaster) and Hodinkee on the Seamaster and Aqua Terra if you want to go full nerd.

If you want something you can order, size, and wear without a two-year relationship with a salesperson, Omega is hard to beat.

Rolex: Godspeed. Most ADs have wait lists, purchase history requirements, or just won't sell you a steel sports model unless you're a regular store visitor. Some people get lucky and walk in at the right time. Most don't. Expect to wait 6-24 months for popular models, or get added to a list that never moves. Can’t shop online.

Tudor: Much easier. Most ADs will sell you a Black Bay 58 or Pelagos 39 without games. You might wait a few weeks for specific configurations, but it's not the Rolex circus. OR just shop online…

Omega: Easiest of the three. Walk into an Omega boutique or AD, try on watches, buy the one you want. Sometimes they'll even negotiate a bit. No games, no wait lists for most models. OR just shop online…

Grey market = authorized dealers selling to unauthorized resellers, or brand new watches being flipped by people who got them at retail. You lose the manufacturer warranty (usually get a grey market dealer warranty instead), but you can get the watch now, for more money.

Pre-owned = used watches, sometimes with box and papers, sometimes without. Can be a great deal if you know what you're looking at.

Trusted retailers:

What to avoid:

If you're buying grey market or pre-owned, do your homework. Check seller reviews, ask for references, and if the price is suspiciously low, walk away.

You're not buying a watch to flip it. You're not buying it to post it. You're buying it because you want something built to last that you'll actually wear, pass down, and look at in 30 years without regret.

That's intentional luxury. Not deprivation (you're spending real money), not flexing (you're choosing for yourself, not Instagram), but a deliberate choice to buy quality once and be done with it.

Time is wealth. The watch on your wrist is a literal reminder of that. Every time you check it, you're choosing how to spend the only resource that matters. So buy the one that makes you want to check it, not because you're worried about being late, but because you like looking at it.

Rolex, Tudor, and Omega all make watches that will outlast you if you take care of them. The question isn't which one is "better." The question is which one fits the life you're actually living.

If you're climbing the corporate ladder and want something people recognize, that's Rolex. If you're building something on your own terms and want a tool you can beat on, that's Tudor. If you want serious watchmaking without the circus, that's Omega.

All three will last a lifetime. Pick the one that matches who you are, not who you think you should be.

Back to the original question: how do you choose between Rolex, Tudor, and Omega for your first serious watch?

Here's the truth: your first brand is like the first band you loved in high school. It shapes your taste, it will always matter to you, but it doesn't have to define you forever. Most watch guys, once they're deep enough into this to read newsletters about it, end up trying different brands over time.

So for a first real watch you plan to wear hard and maybe hand down:

If you want heritage + recognition → Rolex. You've got a stable income, you like the idea of a watch your kids and non-watch friends instantly recognize, and you're willing to either play the AD game or hunt the secondary market intelligently. A Sub, Explorer, GMT Master II, or Datejust will feel like the watch in a way few things can.

If you want heritage + no games → Omega. You care more about wearing the watch than posting the box, and you like stories (moon landings, Bond, Olympics) more than wait lists. A Speedmaster Pro, Seamaster Diver 300M, or Aqua Terra can easily be a one-and-done watch for years, with modern tech and real history behind it.

If you want tool watch + under the radar → Tudor. You like the Rolex vibe but not the spotlight, and you know yourself well enough to admit you'll actually beat on your watch. A Black Bay 58/54 or Pelagos 39 is an easy daily that can take a hit and still look right at dinner, and most people will have no idea what's on your wrist unless they're already watch-pilled.

If you pressed me to give simple, honest recommendations:

In the end, the "right" choice is the one you'll actually strap on, scratch, sweat in, and one day pass to your kid with stories attached. The watch that lives a life on your wrist beats the one that lives as a screenshot in your AD's CRM every time.

Reply and tell me which one you'd choose, or which one you already bought and why.

Whether you went Rolex, Tudor, Omega, or something else entirely, I want to hear what made you pull the trigger.

Time is wealth. The watch is just a reminder. Choose intentionally.

—Ian