How To Dress Like An Oscars Leading Man

The Big Short’s Power Broker

Pre-Financial Crisis, being a banker was a status symbol to be flaunted, not hidden. So suits were pinstriped, collars were contrast and watches cost as much as Liberia’s GDP. Since the crash, however, city style’s grown a touch more restrained, in a rare sign of awareness that ruining millions of lives is at odds with dressing too ostentatiously.

But if you weren’t actually involved in that particular economy-wrecking boondoggle, feel free to take notes from the guys who did. And as Ryan Gosling proves in The Big Short, dressing like a Master of the Universe goes a long way to making you one.

So bring back the power suit by stretching out those skinny lapels you’ve been wearing, and swap your normal navy for a statement-making check. The contrast collar thing is a touch too throwback, so stick to the white shirt (the better to make that pattern pop) then accessorise with an oversized watch; a Rolex if the bonus has landed, a TW Steel if not. We’d advise not adopting the utter disregard for morality, though.

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Revenant’s Urban Woodsman

The story of Leonardo DiCaprio’s arduous journey in pursuit of an Oscar isn’t, on the surface, prime sartorial inspiration. Yes, fur is trending. But while it’s excusable when that hand-skinned pelt is all that stands between you and the hypothermia, it’s an invitation for PETA’s red paint if you try it on the street.

Better, then, to dilute. Leo’s untamed mane veers too far towards hermit, but the beard and long hair look shows, unlike the man himself, no signs of dying; just make sure you treat yours with a leave-in conditioner so your friends don’t abandon you as well.

Then, learn some layering lessons. You might not be in and out of rivers all day, but jumping between frigid streets and commuter trains is, we think, equally arduous. Layer up with lightweight pieces and knits beneath a (faux) fur-lined coat or jacket, so you don’t suffer like Leo.

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Steve Jobs’ Personal Uniform

Steve Jobs’ branding genius wasn’t restricted to Apple’s generation-defining products, it applied to his own wardrobe as well. His mock roll neck – designed by Issey Miyake and bought in bulk – became, through force of attrition, a signature. It was a uniform that cemented his image, and his legend, in the public consciousness.

Of course, copying someone else’s uniform wholesale isn’t so much a signature style as forgery. So emulate Jobs’ simplicity instead. Opt for neutral colours – in his case, black and blue – which allow you to mix and match without worrying about unsightly clashes.

Next, pick a classic piece that few people are wearing; Jobs’ roll neck was avant-garde enough to be distinctive, but not so unusual as to be novelty. Our pick? A granddad-collar shirt, to nail that guru thing. Stock up and wear one everyday. Then just try to build a reputation to match the image.

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Bridge Of Spies’ Cold War Comfort

The first thing you learn in spy school is: don’t talk about spy school. The second is to not stand out. Which is why, in Steven Spielberg thriller Bridge of Spies, Mark Rylance’s Russian spy isn’t dolled up with pocket squares and boutonnières. Nor, for that matter, is Tom Hanks, as the US lawyer sent to negotiate his trade for downed U2 pilot Gary Powers. Because when it’s nuclear war on the line, you need to feel comfortable.

Rylance’s 1960s sack suit takes the idea of dressed-down a touch too far for modern offices. So split the difference between the protagonists and look for unstructured tailoring that fits in the shoulders, but affords you enough room to move; Don Draper’s like-a-glove suits came a few years later.

The shirt: white. The overcoat: Brooks Brothers. The hat: a black Borsalino. And the umbrella: not optional. If only to ensure you can always blend into a crowd.

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The Martian’s Outer Space Athleisure

While we’d love to recommend Matt Damon’s outdoors outfit – a sumptuous white and burnt orange spacesuit that would fulfil all manner of boyhood dreams – it’s not the most practical look. Good for trekking across miles of Martian tundra. Less suited to the pub. If only because you’ll never get your pint past the helmet.

So it’s his inside getup to learn a lesson from. And that lesson is that, no matter the stakes, being comfortable needn’t come at the cost of looking good. Whether dancing (begrudgingly) to disco, or reverse engineering a greenhouse from faeces and fire, a well-cut pair of jersey shorts and a slim-fitting tee or sweatshirt help keep your mind on the job, not your look.

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Mad Max’s Post-Apocalyptic Street Ninja

Sometimes city living can feel like a warzone. And although we wouldn’t advise you don fatigues for work every morning, adopting a martial aesthetic can be particularly empowering. The key to Max’s look is a ballsy silhouette.

So make like Max and taper; broad shoulders, courtesy of an oversized bomber or a shearling biker jacket, with a longline tee and skinny-fit denim (or, if you’re feeling particularly confident, running tights and mesh shorts).

Pick a shade and stick to it: dark greens are on-trend; off-white is dystopian camouflage; and black is a forever fail-safe. Then add in some leather for that road warrior vibe. Jacket, backpack, gloves: yes. Trousers: no. Unless you’re filming the sequel.

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