We all know the Oscars are the ultimate fashion opportunity – a chance for Hollywood’s most glamorous to get glitzy from head to toe. And with no shortage of style options on offer in womenswear, we sure do love to dive into the latest trends in shapes, colours, textures, and accessories… But what about the menswear game? It’s arguably harder to nail the basics when it comes to a good suit (if you’re opting for one). Luckily, these twenty men showed us how to slay the Oscars red carpet with panache – take a peek at our best-dressed men of Oscars past, whose looks were far from boring:
20 men who really upped their style game at the Oscars
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Paul Newman, 1958
A fashion connoisseur from back in the day, Paul looked fashion forward in this dapper tailcoat. The fitted and cropped waistcoat only adds to the elegance. Swoon. Getty Images
Sidney Poitier, 1964
The quintessential gent, Sidney showed them all how it was done way back in 1964. With his open tailcoat jacket and lack of bowtie, he looked original, sharp, and timeless. Getty Images
Robert Downey Jr, 1989
He’s come a long way since then, but back in 1989, RDJ already knew how to turn a few heads. With those embroidered lapels, teal necktie, and green cummerbund, he sure stands out from the crowd. Getty Images
Daniel Day-Lewis, 1990
This may look more like one of his period roles, but Daniel sure upped his style game for the first Oscars of the ‘90s. That wavy hair, long jacket, elaborate necktie, and velvet waistcoat combine to make an unforgettable look. Getty Images
Tim Robbins, 1995
Ok, so it looks cheesy now, but back in the mid-90s, this would have been quite the look. Plus, we appreciate his dedication to standing out with his starry night ensemble, black shirt, and shades – it sure beats your bog standard black and white tux. Getty Images
Benjamin Bratt, 2001
Benjamin looked pretty swish the night of then girlfriend Julia Roberts' Oscar win in 2001. The long dinner jacket over a well-fitting waistcoat, with the crispness of a white tie on a white shirt make him one to beat for style. Getty Images
Matthew McConaughey, 2015
Never one to play by the rules, Matthew broke with protocol when he stepped out in this patterned metallic blazer in 2015. The waistcoat, the bowtie, the facial hair – the whole look is very extra, but in the best way possible. Getty Images
Neil Patrick Harris, 2015
Now here’s something you don’t see every day – an all-grey look on an Oscars red carpet. Yet, NPH’s woollen suit, with the contrasting texture of the satin lapel and bowtie, combine to create an elegantly understated look, and we applaud him for it. Getty Images
David Oyelowo, 2015
David looked super snappy on the red carpet in 2015. Yes, he may have been matching the actual carpet, but somehow, with the pin, matching bowtie, waistcoat, and piping, the two shades work gloriously together to create an original and refreshing Oscars look. Getty Images
Mark Ruffalo, 2016
Surely one of the standouts for men’s fashion, this 2016 look from Mark is a winner in Valentino in our eyes. The choice to go more royal than navy blue was risky, but he pulls it off with a charm and warmth that suits him perfectly. The patent shoes keep things smart, too. Getty Images
Eddie Redmayne, 2016
Now, most people couldn’t pull off a velvet jacket plus velvet slippies with such sophistication, but, Eddie is not most people. Somehow, this coordinated look brings out the matinee idol in him, and we’re digging it. Getty Images
Dev Patel, 2017
This may be one of our favourite men’s Oscars looks of all time. Every element – from the perfect fit, fresh shade of white, the patent shoes, to the slightly ruffled hair – all work beautifully on Dev in Burberry. His fashion moment to beat. Getty Images
Pharrell Williams, 2017
Would we expect anything less than Chanel excellence from Pharrell? Probably not. In this tailcoat jacket, complete with cummerbund, draping necklaces, and glittering brooch, Pharrell made a style statement in 2017 that we’ve scarcely seen before or since. Getty Images
Ansel Elgort, 2018
In a forest green velvet blazer, Ansel looks smart in an old-school kind of way. It’s a strong colour choice – standing out from the rest of the pack, but still formal. And that cute bowtie keeps things traditional. Getty Images
Armie Hammer, 2018
In this custom Giorgio Armani red velvet suit, Armie manages to look suave without looking costume-y – the combination of his stature, and the sharp fit works wonders. If only more men had such daring to think outside of the fashion box. Getty Images
Chadwick Boseman, 2018
Chadwick is a style star to watch, and this Givenchy outfit from last year’s ceremony was our first clue. The embellished knee-length blazer with slim lapels, paired with the collarless shirt hit all the right fashion notes. And the zip-up loafers? It all added up to create a fresh, experimental, yet still dressy look. Getty Images
Daniel Kaluuya, 2018
Now – this is what you call upping your style game. For his very first Oscars, Daniel stepped out in this bronze velvet jacket as the statement piece of his evening wear. The classic black bowtie and lapels provide some excellent framing, and with the matching pants, it’s a sure-fire winner. Getty Images
Miguel, 2018
We love that singer Miguel chose to add an extra touch to his standard dark tux – the draped velvet coat adds some real pizzazz… Who said accessorizing was just for women? Getty Images
Timothée Chalamet, 2018
Ok, so the hair leaves a little (ok, a lot) to be desired, but this perfectly tailored all-white Berluti suit is on point. In fact, it may have been the look that put Timmy on the fashion map. And the Chelsea boots? An ingenious touch. Getty Images
Tom Holland, 2018
Ok, so technically this was at an Oscars after-party, but still. In this burgundy three-piece, Tom shows us that men don’t have to shy away from strong colour. In fact, the rich shade flatters him like nobody’s business, and helps him stand out from a sea of endless black, white, and grey. Getty Images
CTV’s live coverage of the 91st Oscars begins Sunday, February 24 at 5:30 p.m. ET with etalk Live at the Oscars. Don’t miss a minute of the star-studded red carpet action: Follow along on social @etalkctv or join the conversation using #etalkredcarpet! For the latest Oscars news, exclusive interviews and more, visit etalk.ca/Oscars.
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