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The Journal · 16 July 2026

What would they wear today?

Che, Shackleton and Hillary walk into an AD. Pure conjecture, zero apologies — what three giants would strap on at retail, today.

Edmund Hillary, c. 1953. Photographer unknown — public domain.
Edmund Hillary, c. 1953. Photographer unknown — public domain.

A thoroughly unscientific thought experiment, this one. Take three of history’s great hard men, hand them a credit card, and push them through the door of a modern watch retailer. What walks out on the wrist? No vintage allowed, no auctions — retail, TODAY. Let’s go.

Che Guevara — the £7 answer and the honest one

Officially? El Comandante would HAVE to pick up a Casio F-91W — seven quid, keeps better time than his convictions, and the most classless watch ever made in the most literal sense. The revolutionary’s choice. Case closed… except. We’ve all seen the photos, comrade. The man wore a Rolex GMT-Master through an actual guerrilla campaign. Some things transcend ideology, and a Pepsi bezel is clearly one of them — so the honest answer is a GMT-Master II ‘Pepsi’ on a Jubilee, and he’d tell you it was seized in the name of the people. (More on Che’s actual Rolexes in our previous dispatch — it’s quite the story.)

Ernest Shackleton — the Boss picks a Ranger

Sir Ernest Shackleton, before 1909. George Charles Beresford — public domain.
Sir Ernest Shackleton, before 1909. George Charles Beresford — public domain.

Shackleton needs three things: legibility in a whiteout, toughness beyond argument, and a price that won’t upset the expedition’s creditors (of which there were, historically speaking, MANY). That’s a Tudor Ranger — a watch whose entire family tree runs through polar expeditions, no-nonsense, brilliantly legible, and under two grand. The Boss buys it, wears it through something unspeakable, and then quietly pawns it in Punta Arenas to get his men home. Every single one of them, mind you.

Edmund Hillary — the Explorer, obviously. And yet…

The Rolex Explorer exists because of the 1953 Everest expedition — this is the least controversial pick in horology. Hillary walks into the AD, tries the 36mm Explorer, it disappears onto the wrist the way an Explorer does, done. And YET — every watch geek knows the beautiful, contested truth that Hillary carried a Smiths De Luxe up that mountain too, and Smiths ran the ‘first to the top’ adverts to prove it. So he takes the Explorer… then spends the entire dinner party telling everyone the British watch did the real work. As is right and proper.

Disagree violently? Excellent — that’s what the contact form is for. Better yet, come argue in person at the bench.

Broad Arrow Watchworks — from the bench