Some people – you know who you are – say men are difficult to buy for. But, speaking as certified watchaholics, we can tell you nothing could be further from the truth. The only difficulty is which watch to buy for which particular occasion. We do realise that a proper watch is a gift worth waiting (and saving) for, so you probably want to hold out for the traditional Major Life Milestones. (The rest of the time, there are always watch straps, watch cases, watch winders, books about watches… You get the idea.) Here is your one-stop guide to picking a perfect timepiece that he’ll truly appreciate for any given celebration.

A graduation watch, unless you happen to be a mature student or a spoilt teenager, is likely to be your first step into the world of “proper” watches. The good news is it’s not necessary to spend thousands and thousands from the off. The even better news is it’s possible to get something that looks like you did, and could quite happily last a lifetime. Sporty types will want to look at the TAG Heuer Aquaracer, the Montblanc TimeWalker or the Oris Aquis. If you’re after something with more everyday versatility (or heading straight into a corporate trainee scheme), you should consider the Baume & Mercier Classima or just about anything from NOMOS Glashütte or Junghans. Both produce a host of design-conscious, moderately sized and reasonably priced watches, many of which are bona fide classics.

These are the big ones, the milestones that come to us all, approaching with a steady, relentless march. On the plus side, this should mean you – and whoever might be buying you a watch – have had a good few years to plan for it. Bearing in mind the fickle relationship between men and birthday presents (OK, we admit, we are sometimes tricky to buy for), here are some pointers for the big three-O, four-O and five-O.

• _30th birthday _

At this point, a man is starting to know his place in the world. You have probably landed on a career path, no matter how meandering, and have left youthful missteps behind to develop a sense of your own personal style. But you’re not set in your ways just yet. Watch-wise, you’ve probably got at least one decent timepiece that does the job. This is the perfect time to try something a bit different, to embrace a watch with real character. To that end, the right watch could be anything from a Bell & Ross BR 03 to a TAG Heuer Monaco, a Panerai Radiomir or an Oris Carl Brashear chronograph. Think about what you haven’t got – in terms of colour, complications, size or shape – and pick something that fills a gap.   

• 40th birthday

Those early-life milestones are a little bit further away in the rear-view mirror and the watches that came with them – if they did, of course – might have given you the collecting bug. If that’s the case, you’ll know what’s next on the agenda, and probably have a lengthy shopping list, but might we humbly suggest this is the time to remember the classics? This will also work for anyone getting into the watch game at 40. If you’re going to have one serious watch at this age, it should be something that will summon universal respect. That means an IWC SCHAFFHAUSEN Pilot’s watch, a Zenith El Primero chronograph or a Panerai Luminor 1950.

• 50th birthday

The half century is a difficult one. On the one hand, retirement is probably starting to figure in your long-term plans. On the other, you have no intention of feeling or acting like an old man any time soon. Two courses of action present themselves. First, embrace the mid-life crisis and invest in something a bit racy, a chronograph, naturally, which will pair well with the inevitable sports car you’ve also had your eye on. Something like the Bremont Jaguar MKII, perhaps. Alternatively, why not take the opportunity to properly surprise people? Buy a Ressence – any model, they’re all fantastically interesting – and you’ll knock those stereotypes squarely on the head.

There is a distinction to be drawn here between a watch to wear on your wedding day and a watch that you might be given as a wedding gift. Even if you’ve got your heart set on a dive watch or a chronograph, our advice is to put that idea on hold. We trust you’ll be dressed as smartly as possible for the big day and, really, you should be looking at a slim, elegant watch that looks excellent with a suit. That’s something every man should own, and what could be nicer than wearing a new watch that really elevates your outfit on the big day? In terms of what to look for, a leather strap is a must, and keep the complications to a minimum – hours, minutes and seconds are all you need. The Jaeger-LeCoultre Reverso is a superb formal watch. If the rectangular case isn’t to your taste, try the IWC Portofino or a Zenith Elite. For the ultimate in refined simplicity, and if a gold watch is on the cards, the Piaget Altiplano is hard to beat.

Rising up the ranks, whether you’re talking about a new job, a hard-won promotion or the long-awaited “good news” call from your boss, is the perfect excuse to reward yourself with a new watch. Whether you work in the kind of environment where the subtle flash of something new on your wrist will impress people, or whether it’s going to be something you save to enjoy away from work, you have quite literally earned it. Treat yourself, before you adjust to the new normal. Of course, your “new job” watch could be anything, but we’d argue it’s hard to go wrong with a Jaeger-LeCoultre: the brand has something for everyone, from the 1960s-inspired simplicity of the Polaris Automatic, to the refined style of the Master Control Calendar.

The retirement watch, at least as tradition dictates, should have gravitas, dignity and presence. If, as one would surely hope, there’s a corporate budget attached, it should also be cased in gold. Not ones to contradict tradition when these are the stakes, allow us to recommend a Vacheron Constantin Patrimony Hand-Wound, or perhaps a Girard-Perregaux 1966 WW.TC Automatic in rose gold. Sophistication is the name of the game and these are proven winners.

The people featured in this story are not associated with and do not endorse MR PORTER or the products shown