10 Best Milestone Watches for Every Stage of Life

If I could pick a watch to mark each milestone in life, what would they be? Funny you should ask, because I’ve got some ideas — running all the way from under £100 to well over a quarter of a million. These are my personal suggestions for what I like to call “milestone watches” — timepieces that don’t just look great, but also feel like the right companion for life’s big chapters.

Of course, this is my list. There are plenty of other options out there at all budgets, so let me know in the comments what you’d pick for these occasions. But for now, let’s get cracking!

The first major milestone? Graduation. At 16 or 18, I was a spotty, roguishly average teenager who couldn’t be trusted with anything too fancy. So a budget-friendly digital is the way to go.

Enter the Casio G-Shock DW5600, aka the “Original Square G.” Since the 1980s it’s been an icon, and for under £100 you get a shock-proof, 200m water resistant, feature-packed watch that will basically survive anything teenage life throws at it. My version even has solar charging and Multi-Band 6, meaning it’s always accurate without me lifting a finger. Perfect starter milestone watch.

Fast forward a few years. You’ve slogged through essays, exams, or apprenticeships, and it’s time to graduate into the world of work. For this moment, I think it’s time to go mechanical.

My pick is the Seiko Prospex Willard SPB153. It’s one of my favourite modern Seiko divers, with the reliable 6R movement, 200m water resistance, and a tough-as-nails case. It’s versatile, good-looking, and for just under £1,000 second-hand, it feels like a serious step up. A proper tool watch to match that first step into adult life.

Your first real job. Suddenly you’re dressing like an adult (kicking and screaming, maybe), and you need something a little more refined on the wrist.

Enter the Longines Dolce Vita — arguably the best Tank-style watch this side of Cartier. For around £1,500 you get Swiss heritage, sapphire crystal, and elegant design from a criminally underrated brand. In my view, it’s not the “poor man’s Cartier” — it’s a smart, stylish alternative that can hold its own.

Engagement watches are a growing trend, and I’m all for it. Personally, I’d go for the Tudor Black Bay 54.

Slim, vintage-inspired, and wonderfully finished, it’s (in my opinion) the best of the Black Bay range. The in-house MT5400 movement gives you 70 hours of power reserve, plus 200m water resistance, and the overall feel is pure Tudor. At around £3,500, it’s a watch that will last long after the wedding cake is gone.

If you didn’t get a watch at the proposal, marriage is the perfect excuse. And here, my choice is the Grand Seiko Elegance SBGM221.

It’s a beautifully finished GMT with a creamy dial, blued hand, and that famous Zaratsu polishing. The 9S66 movement offers a three-day power reserve, sapphire crystal, and 100m of water resistance. At £4,500, it’s a refined, versatile GADA (Go Anywhere, Do Anything) piece that still feels special.

Babies are expensive, which makes an affordable but meaningful watch the sensible choice. For this milestone, I’d go with the Citizen Forza NJ0180, specifically in Super Titanium.

At £499, it’s light, durable, 100m water resistant, and available in fun dial colours like blue, salmon, and white. An automatic movement and sapphire crystal round it out — a solid milestone watch that doesn’t break the bank when nappies are already draining the budget.

A promotion deserves something a little more celebratory. My choice: the Omega Aqua Terra.

It’s one of the best all-rounders in the business — sporty enough for weekends, elegant enough for the boardroom. You get 150m water resistance, sapphire crystal, and Omega’s brilliant METAS-certified co-axial movement. At £3,500–£6,000 depending on spec, it’s a real reward piece that will keep you smiling every Monday morning.

With kid number two, you need practicality. A watch that can handle rough-and-tumble family life but still look great.

That’s where the Hamilton Khaki Field Auto comes in. I’d go for the 38mm version — it wears beautifully and has the right balance of rugged and refined. For under £1,000 you get Swiss heritage, sapphire crystal, 100m water resistance, and a timeless field watch design that feels right at home at the playground or on date night.

Few milestones are bigger (or scarier) than starting your own business. Once things settle and money starts flowing, why not celebrate with something unique?

For me, that’s the Farer Worldtimer. It’s British, beautifully designed, and genuinely useful for the entrepreneur juggling time zones. The dial options are stunning, and the build quality is excellent. At £1,495, it’s an attainable yet meaningful choice from a brand with real independent spirit.

Finally, retirement. And here, I’m going full classic with the Rolex GMT-Master 1675 Pepsi.

It’s vintage Rolex at its best: slim, comfortable, and endlessly stylish. I think it wears better than any of Rolex’s current sports models, and it’s the kind of watch that feels like a proper full-stop on a career. Prices range from £8,000–£12,000 depending on condition, but it’s a retirement splurge worth every penny.

If you’ve made it into multi-millionaire territory, why not? My “money no object” choice is the Jaeger-LeCoultre Reverso.

From simple time-only versions to wild minute repeaters, the Reverso is an Art Deco icon that can be tailored to any taste. Prices start around £6,400 and climb to nearly £300,000, but if you’ve made it that far in life, budget probably isn’t your top concern.

That’s my list of milestone watches — but what would yours look like? Maybe I should have included icons like the Cartier Santos, Omega Speedmaster, or TAG Monaco. Or perhaps independent brands like Fears, Christopher Ward, and Ming deserve a place.

Either way, these are my picks for 10 big life events, plus one dream “money no object” option. Now over to you — which watches would mark your milestones?