12 watches favoured by history's most stylish men

DOES A WATCH make a man? Or perhaps it’s the other way around? Whichever way you decide to view it, there’s no doubt that by looking at the history books, a cohort of men have stood out for their stylish pursuits. But not all eyes have been focused on their brooding good looks or the clothes on their back, but rather, the watch on their wrist.

For some of these stylish icons we talk about, like Mr. Paul Newman, it’s well documented that he wore the same watch for decades: his Rolex Daytona “Paul Newman” ref. 6239, a watch immortalised by the last Hollywood movie star, and one that would later sell for a whopping $26.5 million at auction in 2017 (the most paid-for a watch at the time). These timepieces weren’t the product of some flashy brand ambassador deal but rather the choice of its wearer, which says something.

In the context of important watches worn by important (stylish) men, Esquire has rounded up 12 of the most stylish men from yesteryear and today and the signature watches they favoured.

1

PAUL NEWMAN

Rolex Daytona ref. 6239. 

Arguably the most famous watch in the world that was worn by the world’s most famous actor at the time. The Paul Newman Daytona is the watch that sparked the craze in Rolex Daytonas (and the ability to actually purchase one). and there’s no doubt that this reference 6239, with its white exotic dial, will go down as one of the most important timepieces of all time.

2

IDRIS ELBA

Gucci 25H Tourbillon

Ok, Idris Elba might have been the face of the Gucci 25H campaign but there’s two things we can deduct from the image to your left. One, Elba is a massive watch guy and he looks pretty thrilled with the stunning watch on his wrist. Two, this isn’t the first time he’s rocked the 25H Tourbillon outside of Gucci-duties. He continues to wear the $200,000 Gucci 25H Tourbillon (ref. YA163307). Why? Because it’s one helluva timepiece, and Elba obviously thinks so, too.

3

ROBERT REDFORD

Rolex Red Submariner ref. 1680 

Ah, Redford’s classic Rolex “Red Sub”. Not only an extremely difficult vintage piece to track down these days – Rolex only produced ref. 1680 between 1967 and 1969 – but one of the coolest non-traditional Submariners that Rolex made; it was also one of the first subs to feature a date window. Redford was definitely a fan, so much so that he wore his own Red Sub in films such as All The President’s Men .

4

GIANNI AGNELLI

Omega Seamaster Professional 600M PloProf 

Gianni Agnelli, the Italian industrialist whose family founded Fiat, was long known for his effortless, natural style (in other words, “Sprezzatura”). But aside from his fine Neapolitan tailoring and collection of luxury cars, Agnelli was renowned for his taste in watches; a taste that was widely different to any other watch collector at the time. Pictured here is his rather gargantuan Omega Seamaster “PloProf”. Not one for subtleties, Agnelli worn the PloProf particularly during ski trips to St. Moritz. Over the shirt cuff was his signature style trait, and if anyone could pull off a 55mm watch, it was Agnelli.

5

HENRY GOLDING

Patek Philippe Nautilus ref. 5711/1A 

Henry Golding is a watch guy, through and through. The Hollywood megastar has made public his small but thoughtful watch collection – which includes a Tudor Black Bay, Cartier Tank and vintage Omega Seamaster. But standing out from the pack is his Patek Philippe Nautilus 5711. The watch you’ll see him wear most, Golding pulls off the Nautilus with a great deal of charm and sophistication, no matter the occasion.

6

DON DRAPER

Jaeger-LeCoultre Reverso Classique

While Don Draper is a fictional character in a fictional TV show – albeit one of the most stylish men to have graced our screens – his Jaeger LeCoultre Reverso Classique is every bit real. And it’s particularly telling as to where Draper is in his life and who he is as a person. It’s Season 2 of Mad Men, and Draper just received a raise as well as making partner at Sterling Cooper. This is the watch he buys himself, and the watch that, perhaps, best represents who he is as a person: two-sided.  

7

JOHN MAYER

IWC Big Pilot ref. IW5002 

John Mayer might be one of the greatest musicians of our generation, but his unique and highly coveted watch collection might impress some more than one of his dazzling blues licks. Back in 2013, Mayer gave Hodinkee founder Ben Clymer unprecedented access to his collection – and the meaning behind each piece, like this IWC Big Pilot. “The Big Pilot reference 5002… from 2002 to 2006, I’m wearing this watch on stage every single night.” 

8

Sir Lewis Hamilton

IWC Big Pilot’s Watch

LH44 has only really become a watch guy in recent times, most notably after joining Mercedes who subsequently signed a partnership deal with the brand he’s now most famous for repping. He’s won seven Formula One World Championships since then, most of the time rocking some variant of IWC’s Big Pilot Watch throughout his hundreds of stints on the podium, becoming perhaps as synonymous with one type of watch as any driver before him.

9

John F. Kennedy

 Rolex Day Date

The most stylish President in history, JFK had a famed rotation of watches, but perhaps the most famous was the Rolex Day-Date that really solidified the model’s reputation as the ‘Presidential’ watch that it enjoys today. Of course, the all-gold model carried with it some notoriety due to it being given as a gift to Kennedy by Marilyn Monroe, with the message “JACK, with love as always from MARILYN, May 29th 1962.”  

10

Daniel Craig

Omega Seamaster

Craig’s stint as 007 revamped the character in a bunch of ways, chief among which was bringing the fictional secret agent back into the forefold as one of the pre-eminent style icons of the modern age. Omega, who have provided watches for the franchise since the ‘90s, have been along for the ride the whole time, with Craig wearing some variant of the Seamaster both in the movies and on the red carpet trail for almost two decades.

11

Ryan Gosling

TAG Heuer Carrera

While he’s been a heart-throb for over a decade at this point, Ryan Gosling’s emergence as a “watch guy”, so to speak, is much more recent. Only a couple of years ago did the actor ink his first major watch deal, signing on with TAG Heuer to become the natural spiritual successor to chisel-jawed megastars like Steve McQueen, who as we’re about to discuss, also most famously rocked a Barbie-pink TAG Heuer.

12

Tyler, The Creator

Cartier Crash

While Cartier has a long list of celebrity ambassadors as dignified and elegant as the brand itself, perhaps its most important modern-day spokesman has, in fact, been rapper Tyler The Creator, who has spent most of his last few recent years at the top of menswear Mt Olympus showcasing an impressive collection of Cartier dress watches. It’s the Warholian Crash he’s perhaps most renowned for bringing back into vogue.

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