My grandfather was a big outdoorsman, and he specifically left me his rifle and his hunting knife when he died. I am not an outdoorsman, and have zero use for either of these items. I keep them (in a box, in my garage) because they were his, and because it is meaningful to me that he wanted me to have them. But I have no idea if they were expensive or not, if the rifle still works, etc. And I don’t really care.

I also have my grandpa’s old trucker jacket, which he used to wear all the time, and which he probably bought cheap at a Montgomery Ward or something. It’s held up remarkably well, it fits me perfectly, and it actually suits my style quite a bit. And more importantly, I associate this jacket with my grandpa way more than the knife and gun I never saw him use, and it has much more sentimental value to me. I wear it occasionally, and always think of him when I do. My grandpa did not intend to pass this down to me, and probably would be surprised to learn I’ve kept it. But it’s definitely one of those things I would try to save in a fire.

It’s a lovely idea to keep a watch you intend to pass down to your kids, but I don’t know how useful it is to worry about having a watch that’s “worthy” of being an heirloom, or to think about whether it will be affordable to service… It’s at best a coin flip whether it gets worn at all. And the item of yours that actually becomes a part of their life might be something you’d never suspect.

Exactly. The Moonswatch didn’t just have the timing and the novelty factor going for it—both of which were huge—but also the fact that pretty much everyone who has even a passing familiarity with watches knows what a Speedmaster is. Probably second only to various Rolex models on the “oh yeah, I’ve heard of that before” familiarity scale. You have to be relatively deep into watches already to know or care what the Fifty Fathoms is — and most of those people probably aren’t the types who will buy a $400 plastic Swatch.

This isn’t directed at OP (who asked a perfectly normal and legitimate question), but I feel like I’ve personally encountered this debate at least a hundred times (probably much more) on various forums over the years, and at a certain point, like…is it really that big a deal to just take off your watch while swimming? How often do you absolutely, absolutely need to know the time while submerged in water? (Assuming you’re not a diver, which few watch people are. And the surfers I know either wear G Shocks, or else don’t give a shit what time it is, which is why they became surfers.) If you’re someone who finds themselves searching the internet for horror stories about 100m watches getting ruined in kiddie pools and getting worried…just take it off when you go in the pool, man. You’ll feel better. No one’s gonna judge you, and you probably won’t need it there. Feel like the water resistance question has become a much bigger deal than it needs to be.

These are all excellent watches, and they are all completely different in looks, function, and formality. It’s almost like asking if you should buy a Range Rover, an Audi, or a Harley.

I would try them all on, and just pick the one whose looks you like the best, and that you could most easily see yourself wearing every day. Your immediate instinct upon seeing them on your wrist will be 100x more valuable than the opinions of strangers.

Omega Railmaster. You can get it grey for like $3k. A beautiful, endlessly versatile, perfectly subtle little watch with all the same quality as the Seamasters but zero of the flash. You can wear it every day and I guarantee one will ever notice it. (I’ve heard rumors there are people who like to get compliments on their watch, but I guess I’m built different.)

You say that now, but when I’m exactly 1.5 seconds late to the big meeting and you’re 3.75 seconds late, you’ll wish your watch had this kind of accuracy.

I applaud you for a genuinely unpopular take. I disagree, but will upvote you just to be contrary.

I’m genuinely embarrassed by the number of scammers and criminals who have gotten busted thanks to YouTube videos and IG posts in recent years. You’re running a profitable criminal enterprise, all you have to do is keep your mouth and don’t attract unnecessary attention, and you blow it all up and give the DA a case for a few likes from strangers on the internet? Truly a disgrace to the fine, noble history of con men and organized crime.

Hardly anyone actually prefers a scratched up watch to a pristine one, so it’s definitely not like you’re wrong to feel that way. But of course, the only way to avoid scratching a watch is to never wear it. The trick is just to accept that it’s gonna happen (and happen again, and again, and…) and try to look at it as getting your money’s worth out of the watch: it’s not a delicate, expensive bauble that you bought to admire—if that’s what you want, you might as well just save your money and drop by the watch dealer and stare at it once in a while—it’s a thing you own and wear and use. Anytime you use anything, it’s gonna leave a mark, both metaphorically and literally.

It is worth keeping in mind when buying a watch, though. Whenever I see a beautiful, gleaming watch with all polished surfaces and wide steel bezels, I remind myself, “this watch will look like that for a month, tops.” Before you buy a watch, maybe check out used watch listings and see if you still like it when it’s been banged up a bit. Because yours will look like that eventually. Does it still look good? Do the scratches and dings give it “character,” or does it just look like a beat-up watch?

Just a taste thing, really. The 556 has always struck me as being just about the least visually interesting watch imaginable, and I really don’t see the appeal—and I’m kind of a meat and potatoes field watch guy, but come on, give me something—so I just chalk it up to different strokes/different folks. It’s cool, just very much not for me.

(I do kind of laugh at the standard Sinn fan argument I see a lot: “this isn’t a fashion accessory, it’s a tool.” Come on bro. No one’s spending more than a grand on an automatic wristwatch purely because of its practical properties. It’s a pricy fashion accessory that you think communicates “I am not the kind of guy who acknowledges buying pricy fashion accessories.”)

The dive watch (as well as the field watch, the pilots watch…) has followed the same trajectory as so many other items of menswear. Think about the bomber jacket, the desert boot, aviator sunglasses, driving loafers, 1980s basketball sneakers, etc etc — all of these items once had a very specific purpose, and all have long since outlived that purpose as a more general-interest fashion staple. There are tons of thoroughly modern incarnations of all these items, but plenty of them hew pretty close to the more traditional designs, because, after all, it was those original designs that inspired people to say “I don’t actually need that piece of gear, but goddamn it looks cool” in the first place.

It makes sense that a lot of people would want a Sub-type dive watch, the same way it makes sense that a lot of people want an Alpha Industries-style bomber jacket. That was the design that made the whole style catch on. And, for me, the fact that most dive watch owners aren’t scuba divers isn’t any more scandalous than bomber jacket wearers not being pilots, or Air Jordan 4 wearers not playing basketball in them.