How to be the most stylish guy at the Oscars

For Pharrell Williams, 2014 was looking pretty good. He’d won four Grammys, given a stellar closing performance at the Brits, and then this happened: he turned up to the Oscars with half his trousers missing. Just when we thought nothing could top the returning Mountie hat saga, his Lanvin shorts marked a new sartorial misfire. We’re not saying Mr Williams missed out on the Best Original Song gong for giving his kneecaps more airtime than Anne Hathaway in Le Mis, but… 

According to the fashion rule book, Moonlight’s Mahershala Ali should have joined Sonny Bono (circa 1968) in the ‘send over a stylist’ category. But at the 2017 Oscars he rocked all black in a Zegna Couture tux with a level of sophistication unseen since Paul Newman put on his fist rollneck. He wore a black shirt, black bow tie and black shoes, accessorised with a vintage-inspired monochrome pocket square. As the first Muslim actor to win an Oscar, we should have known if anyone was going to break with convention and look so slick in the process, it was going to be this guy. 

If Jared Leto can’t pull it off, you should probably give it a miss. And by ‘it’, we mean the 1970s-influenced lilac tuxedo he wore in 2015. Yes, it might have been designed by Givenchy, but that doesn’t stop the Dallas Buyers’ Club actor from looking like the sartorially challenged nephew of Harry Dune. Jared, we get it, sometimes you need a night off from being the rock’n’roll sex symbol with the tattooed torso and perfectly tousled Jesus hair. But next time, instead of igniting a flower-power renaissance on the red carpet, maybe consider doing it at an ABBA tribute night?

No, we don’t mean the kind you buy your Grandad for Christmas. We’re talking about a waistcoat, here – the ‘three’ in three-piece. Worn correctly, a waistcoat has the power to lift and control your midsection, better define your torso and create the illusion of a slimmer silhouette. If you’re really lucky you might even resemble Hugh Jackman in the custom-made Burberry three-piece he wore to host the 2009 Oscars. Actor, singer, dancer, ‘sexiest man alive’ – however you may know him, add ‘expert wearer of the waistcoat’ to the list.

As the most nominated black actor in Oscar history, Denzel Washington is no stranger to awards season. Though you’d never guess so from his wardrobe choices. To be fair, he looked pretty sharp at the 2002 ceremony – and 2010 wasn’t a bad year, either. But then 2013 happened. Attending the Nominees Luncheon as a Best Actor contender for Flight, he paired a classic dad suit with oversized trousers which seemed to be concealing a mild case of rickets. The colour was bad, the tailoring was even worse, and his pained expression suggested that he knew it. 

Hugh Hefner gave velvet something of a bad name. But trust us, if it’s silky and made by Alexander McQueen, then you ought to be wearing it. You only need to take a look at the immaculately tailored skinny-fit tuxedo that Eddie Redmayne wore to the 2016 Academy Awards to convert to the smooth side. Though winning back-to-back Best Actor awards wasn’t to be for Redmayne – Leonardo DiCaprio hugging the inside of a horse’s intestine put paid to that – he proved that velvet is as much at home on the back of a British institution-in-the-making as it is at the Playboy Mansion. Bravo, sir.

You've got to give it to the man - he's consistent. It's a shame that what he's consistently doing is dominating the top spot on every imaginable worst dressed list. This Magnificent Seven, Pirates of the Caribbean inspired ensemble is Brand's eccentric and androgynous street style - spot the signature leather belt, cowboy shoes and V neck shirt - bathed in a tub of unicorn tears. Sure, we never expected this untamed beast to play mannequin to Tom Ford and walk the red carpet in a classic slim-fit tuxedo. But he could have at least found some trousers that hadn't been attacked by a pot of TipEx.

Think of the 1920s and flapper girls and Fitzgerald come to mind. The modern dinner jacket marked freedom from tall wing collars and cravats, and elevated even the most ordinary Joe into a Jay. So slick back that fringe, embrace a little Downton dress-up, fill that glass with a Gin Rickey – and count yourselves lucky that you can now analyse bid prices free from the fear of being crucified by your frock coat.

Unless featuring on TMZ’s homepage or one-upping Janet Jackson is the desired outcome, keeping your, er, statue out of view of the Academy, the media and your mum might be something to consider. Jackass star Steve-O missed the memo in 2006, and walked the red carpet wearing only his infamous tattoos, which included a portrait of himself and the words ‘your name’ on his right buttock (and people say Tinder killed romance). So wear silk, velvet, suede, a one button, a peak lapel, a top hat. Hell, give Anna Wintour something to write about and wear white socks. But for the love of Vogue, wear something.