The watches to mark a man’s milestones – from first job to retirement
Every milestone deserves a timepiece. Here are the watches worth wearing – and keeping – through career, marriage, family and beyond.
A meaningful watch collection can become a record of life itself – from early career ambition and marriage to family, success and retirement. (Art: CNA/Chern Ling)
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For men in Singapore, life often unfolds in chapters: school, National Service, career, relationships, family and retirement. At the risk of sounding reductive, it can be summed up in a few stages, marked by milestones, money and, occasionally, mild panic.
But as memories fade, relationships come and go, and hairlines retreat, one thing stays with you: your mechanical watch collection. If you’re the sort of person who buys a watch to mark a milestone, that collection takes on even more meaning.
Here’s a typical Singaporean man’s life, told in seven stages through the watches that mark the journey.
STAGE 1: YOUR FIRST REAL JOB – THAT SWEET TASTE OF FREEDOM
So, you’ve just graduated and landed your first full-time gig. Congrats. That first pay cheque hits different. It’s thrilling and empowering, but also bewildering. One day, you’re relying on the Bank of Mum and Dad for everything – groceries, petrol, your EZ-Link card – and the next, you’re on your own.
You’re navigating CPF, insurance plans and investment options, and realising that your take-home pay isn’t the number in your contract. Welcome to financial independence, and to the end of buying oat milk lattes without checking your bank balance.
The starter watch
If you’re starting out in a plum sector – finance, tech or law – you might be tempted to treat yourself to something nice. But given the cost of living (or the cost of your lifestyle), a fickle job market and general unpredictability, it’s worth considering watches that are easier on the wallet.
They should also be sleek, discreet, robust and versatile enough for everything from gym sessions and client dinners to networking with peers and senior colleagues. Consider them a daily reminder that you’re no longer living off your parents.
Nomos Minimatik 39 Date Blue (Ref. 1252)
Admittedly, this minimalist piece sits at the pricier end of entry-level, but you’re paying for superlative quality. The spare dial design will appeal to creatives, while the beautifully handcrafted manual-winding movement – visible through the caseback – should appeal to tech bros and engineering types.
Seiko Presage SPB465
It’s hard to find fault with the Seiko Presage series. Designed as the quintessential salaryman watch – classic, elegant, practical and durable, and built for everyday wear in a business setting – this version adds a richly textured dial and a newly developed bracelet for a better fit on the wrist.
Tissot PRX Titanium 38mm
We’ve long been fans of the Tissot PRX, and this edition, launched in November 2025, made us swoon. Its integrated titanium case and bracelet feature alternating brushed and polished finishes, while the hands, markers and date window are accented in a rose gold hue that contrasts beautifully with the anthracite dial.
STAGE 2: CLIMBING THE LADDER OR BUILDING YOUR OWN
By your 30s, you should be in the swing of things. You’re on LinkedIn all day, those early corporate connections are paying off, and you’re in line for a promotion or a regional role. A foreign posting might sound daunting, but the resume boost – and the allowance – can make it worthwhile.
Or maybe you’ve decided to strike out on your own. Just remember: when you’re your own boss, you wear all the hats at once – HR, finance, marketing, office cleaner and, occasionally, customer service punching bag.
The watch that signals momentum
Whether you’re climbing the corporate ladder or building something of your own, it’s time to level up your watch game. Think of something with more flair – perhaps an upgrade in material or finishing – and enough brand recognition to signal to potential partners, professional or romantic, that you’re one to watch.
Breitling Superocean Heritage B01 Chronograph 42 (Ref. AB0156161C1A1)
Yes, it’s a dive watch, but the Superocean Heritage’s stylish looks – tone-on-tone subdials and a well-proportioned dial and bezel – paired with a Milanese bracelet give off a “just spent my birthday weekend on a yacht” vibe. It’s loaded with history too: the original launched in 1957, while modern versions come with in-house movements and ceramic bezels.
Cartier Santos de Cartier (Ref. W2SA0016)
In the corporate world, you’ll spot the Cartier Santos everywhere, and for good reason. It’s good-looking, versatile, classic, recognisable at 10 paces and available in multiple executions: a no-brainer, really. For those venturing abroad or striking out on their own, there’s also inspiration in the story of Louis Cartier and Brazilian aviator Alberto Santos-Dumont, who together created the Santos in 1904, widely regarded as the world’s first men’s wristwatch.
Tag Heuer Monaco Chronograph (Ref. CAW211P.FC6356)
A square watch signals unconventionality and might even suggest someone suited to a role like Chief Innovation Officer. Enter the iconic Tag Heuer Monaco: the world’s first square waterproof chronograph and a fixture on Steve McQueen’s wrist. It practically begs to be worn to the F1 Night Race, from the Paddock Club to the after-parties.
STAGE 3: THE BIG DAY
First comes love, then comes marriage. And then the wedding, the party of a lifetime, where you seal the deal with hundreds of your nearest and dearest. You start dropping terms like “minimum table guarantees” and “weekend surcharge” into daily conversation, and spend your evenings discussing wedding options with your other half. But once it’s all done and dusted, you’re standing there saying, “I do.” Worth every minute.
The couples’ watch: a pair that tells a story
Congrats on your nuptials. You’ve exchanged rings – why not exchange watches too? Since you’ve already spent a fortune on the wedding and honeymoon, there’s no need to go overboard. Maybe opt for a little sparkle, enough to echo the bubbles in your champagne toast, but not so much that the watches stop being everyday wearables. Bonus points if they’re engravable, and a solid caseback helps. After all, memories may dim, but a laser etching lasts forever.
Chanel J12 Bleu Watch Calibre 12.1, 38mm & Chanel J12 Bleu Watch Calibre 12.2, 33mm
In 2025, Chanel released the J12 Bleu series to mark the J12’s 25th anniversary. This alluring midnight blue was a favourite of founder Gabrielle Chanel, who used it in her evening gowns. The 38mm and 33mm automatic models make a perfect pair – both showcase difficult-to-achieve baguette-cut patterns on their ceramic bezels. Beyond the difference in size, you can tell them apart by their hour markers: the 38mm has tone-on-tone numerals, while the 33mm is set with diamonds.
Chopard Happy Sport & Chopard Happy Hearts
Chopard’s quartz-powered Happy Sport (for him) and Happy Hearts (for her) tick all the right boxes for a wedding – or an anniversary. On the gent’s model, ethical rose gold and diamonds evoke celebratory champagne toasts; on the ladies’ model, two heart-shaped floating diamonds speak for themselves.
Jaeger-LeCoultre Reverso Tribute Monoface
Like your wedding band, this Reverso is an everyday wearable with an engravable caseback. It doesn’t get much more classic: its design derives from the original 1931 model, with proportions that suit virtually any wrist. The Fagliano calfskin strap features a Saffiano finish for added durability.
STAGE 4: YOUR FIRST HOME
Time to make your own nest and feather it. Whether you’re buying a BTO flat or private property, this is the biggest financial commitment you’ve made yet. It’s also proof that you’re a fully functioning adult, and a reminder of how far you’ve come from living rent-free at home. Now, all you talk about is renovation timelines and interior design rabbit holes.
The iconic classic
Keys in hand, renovation quotes in your inbox. Owning your first property is a big deal, so mark it with a watch that made history. Think the first watch on the moon, or the first high-frequency automatic chronograph. Something solid and dependable, without draining what’s left of your renovation fund.
Hublot Classic Fusion
The Classic Fusion harks back to Hublot’s beginnings in 1980, when the brand burst onto the scene with the daring pairing of a yellow gold case and a rubber strap – the horological equivalent of a tuxedo jacket with denim jeans. Today, such high-low combinations are commonplace, but that pioneering spirit lives on in three sizes: 33mm, 38mm and 42mm.
Omega Speedmaster Calibre 321
There are dozens of Moonwatches to choose from, but for historical accuracy, the Speedmaster Calibre 321 is your best bet. This steel reissue houses a faithfully recreated Calibre 321 movement – the same one used in the first moon landing – visible through the caseback. Note the column-wheel construction: it is more complex and more desirable than the later, more cost-effective Calibre 861/1861 used in subsequent missions.
Zenith Chronomaster Revival El Primero A384
In 1969, the race was on to produce the world’s first automatic chronograph. Depending on how you define “first”, Zenith, Heuer and Seiko all have a claim. No disrespect to the others, but we simply adore the El Primero A384, with its distinctive tonneau case, panda dial and high-beat column-wheel movement capable of measuring to one-tenth of a second. The Chronomaster Revival is a faithful reproduction.
STAGE 5: YOUR FIRSTBORN
Your world turns topsy-turvy the moment your first child arrives. Any spare time is now spent researching and shopping for diapers, strollers, insurance and childcare options – overwhelming and expensive, yes, but also a beautiful rite of passage. Nothing, absolutely nothing, compares to hearing that first giggle and those first words.
The heirlooms begin
Your thoughts now turn to legacy. What watch might your child want to inherit one day? It should be timeless and emotionally resonant; something that, for now, recalls your baby’s first moments every time you glance at the dial.
A. Lange & Sohne Lange 1 Daymatic
The Lange 1 Daymatic is what happens when German precision loosens its tie – just slightly. A rare automatic from A. Lange & Sohne, it upends expectations with a mirrored dial layout, with the day display at 6 o’clock and the signature outsized date at the top. Inside is a gorgeously finished in-house movement – pure Glashutte poetry. As the self-winding counterpart to the 1994 Lange 1 – the watch that helped resurrect German haute horlogerie – it carries the spirit of new beginnings in its very name, making it a fitting tribute to a firstborn. The 2025 Honeygold edition, limited to 250 pieces, makes the occasion feel even rarer.
Breguet Tradition 7057
First-time fathers experience a whole spectrum of raw emotions – from love and joy to doubt and anxiety. Like them, Breguet’s Tradition 7057 lays bare its soul: the dial is reduced to the upper portion, while the exposed central plate showcases the bridges, gear train, escapement and traditional pare-chute shock-absorbing mechanism. It comes in 18K white gold.
Patek Philippe Calatrava Ref. 6196P-001
Like all Calatravas, this stately 950 platinum piece – with its salmon dial and chocolate alligator strap – is minimalist and refined. The manual-winding calibre, visible through the caseback, is impossibly beautiful – much like your newborn. There’s also a diamond set into the case at 6 o’clock, a reminder of just how precious they are.
STAGE 6: CAREER PEAK AND YOUR MENTOR ERA
By your 40s, you’re likely at the peak of your profession – highly skilled and well respected. Maybe your company is scaling, pushing overseas, raising funds or going public. And here you are, mentoring the next generation and passing down wisdom, along with a few life hacks – from relationships to renovations.
Precious metal pivot
If you’ve been holding back on a precious metal watch, now’s the time. As an official daddy, uncle or sir, you can wear a full yellow gold ticker – hello, Daytona – with confidence and a sense of humour. Or perhaps a timepiece from your birth year? The late 1970s to mid-1980s fell right in the middle of the quartz crisis that shook the mechanical watch industry, but some gems emerged from the period.
Casio G-Shock MRG-B2000KT-3A
Yes, the G-Shock is one of the icons born during the quartz crisis, when quartz watches flooded the market. Today, it sits in a class of its own. This model features a hand-engraved phoenix motif by renowned metalsmith Kobayashi Masao, symbolising prosperity and longevity. The titanium case and clasp undergo deep-layer hardening and AIP coating for superior durability, while the crystallised finish and kurogane-iro green DLC coating evoke traditional swordcraft.
IWC Ingenieur Perpetual Calendar 41
Another gem from that era, introduced in 1985, is IWC’s Perpetual Calendar, developed by then-head watchmaker Kurt Klaus. Originally housed in the Da Vinci case, the movement and its variations now appear across IWC’s portfolio. We have a soft spot for the Ingenieur line because of its purity of design. This stainless steel edition is the perfect backdrop for Klaus’s ingenious mechanism: comprising around 80 parts, it allows seamless adjustment of the displays and offers impressive long-term accuracy.
Piaget Polo 79
More bracelet than watch, the original Piaget Polo debuted in 1979 with a bold, all-gold integrated design that showed off Piaget’s mastery of ultra-thin movements and jewellery-making. The watch became known for its fluid construction and exquisite finishing. Today’s revival features an automatic in-house movement visible through the sapphire caseback. It comes in 18K yellow gold.
STAGE 7: RETIREMENT, A.K.A. FINAL BOSS LEVEL
In your 60s, you’re ready to wind things down or sell the business you built from scratch. You’ve toiled long enough; it’s time to swap pressure for pleasure, and KPIs and ROIs for YOLOs and JOMOs. Now, where was that 30-day cruise itinerary you saw the other day?
The final flex
Business sold, goals achieved. The watches you acquire now are the ones you’ve dreamed about for years – a statement piece, a victory lap, a gift to yourself. And your final boss watch doesn’t have to mark the end of your collecting journey; it could just as easily be the start of a whole new chapter.
Audemars Piguet Royal Oak Perpetual Calendar Ref. 26674
Audemars Piguet celebrated its 150th anniversary in 2025 by releasing a new-generation perpetual calendar with Calibre 7138. Housed in a sand gold case that exudes quiet luxury, it also impresses with its user-friendliness: owners need only the crown to adjust all calendar and timekeeping functions. The sleek 9.5mm case height is another plus. It’s no wonder the watch took home the Iconic Watch Prize at the 2025 Grand Prix d’Horlogerie de Geneve.
Corum Heritage Coin
There’s another president’s watch that deserves attention: Corum’s Heritage Coin. Hewn from an authentic US$20 gold coin, split in half so that one side forms the dial and the other the caseback, it makes for quite the conversation piece. It has been worn by US presidents from Richard Nixon and Ronald Reagan to George Bush Sr and Bill Clinton – good company indeed.
Patek Philippe Nautilus Ref. 5811/1G-001
We couldn’t leave out the Nautilus, not when it’s the gold standard of final-boss watches. Speaking of gold, the 5811 comes in white gold rather than steel, unlike its predecessor, the 5711, which makes it a heftier wear. The in-house movement has also been upgraded, and the integrated bracelet clasp now features micro-adjustment.
