The Leonardo DiCaprio guide to supercharging simple tailoring (with the help of a shiny new Rolex)

WHEN YOU SEE LEONARDO DICAPRIO in the wild, he’s usually wearing his undercover celeb uniform: baseball cap, sunglasses, face mask etc. But for the London premiere of One Battle After Another, the 50-year-old actor stepped things up a gear.

Considering it’s one of the most highly anticipated films of the year, we’d expect nothing less. Inspired by Thomas Pynchon’s postmodern novel Vineland and directed by Paul Thomas Anderson, the starry OBAA cast includes Teyana Taylor, Benicio del Toro and Sean Penn – and of course Leo, playing the washed-up, mustachioed revolutionary Bob Ferguson.

In London this week, the Academy Award winner schooled us all on how to wear timeless tailoring – and there are a couple of subtleties that pulls it all together. Let’s start with the suit: though he chose a simple black single-breasted two-piece, it’s one which fits impeccably. The relaxed yet nipped jacket. The straight leg. The slight break on the shoe. All small details which, together, make him look like a straight up tailoring pro.

What really takes it up a notch, though, is the matching black dress shirt. Where a white shirt can sometimes look a little security guard-coded, a black shirt is a sleek cool-guy alt that’s an understated point of difference. If you look at the red carpet group shot, for instance, you’ll see how DiCaprio is the only one who looks like he really gets menswear. And guess what? He’s the only one in a black shirt.

That’s all before you get to his watch. He wore a polished Rolex Land Dweller, a buzzy new 2025 addition to the Swiss marque’s catalogue which is set to become one of the enduring classics. Considering the Wolf of Wall Street actor was announced as an official Rollie ambassador (or, in the brand’s words, Testimonee) back in February, it feels like the perfect choice.

Besides the fact that it’s a watch with cachet, it’s also the kind of timepiece that has the ability to elevate anything you wear it with. Take DiCaprio’s outfit, for example – just a glimpse of the Land Dweller’s integrated case, fluted bezel and honeycomb dial is enough to supercharge a simple black suit with some sophisticated menswear finesse.

And, if you’re into watches, you’ll be impressed with the updates behind the scenes, too. The Land Dweller is fitted with Rolex’s new Dynapulse escapement – a low-friction, low-mass dual-wheel system crafted from monocrystalline silicon – and the calibre 7135 which has hugely increased the beat of the movement (to a previously unattainable 36,000 vibrations per hour) while maintaining the full 66 hour power reserve.

Rolex Land Dweller 40 mm Oyster

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Ultimately, there’s a few key takeaways from DiCaprio’s look. Number one: you need a tailor. Number two: you need a black shirt. And number three: you need a Rolex. Or, if you don’t have a spare £30k lying around, try a Tissot instead. Simple.

A version of this story first appeared on Esquire UK.