You couldn’t call it a boring year for menswear, could you? Looking back, it’s arguably been one of the most diverse, colourful and expressive spells we’ve had in a long time. Clothes became fun again. Menswear trends were chaotic and contradictory. People let go. Men got confident. Slim-fit minimalism found itself edged out.
This was the year when 23-year-old Timothée Chalamet and 66-year-old Pierce Brosnan could both become style icons. The ’90s were trending, but so were the ’70s, ’50s and ’80s. Tailoring loosened up, sustainability got serious, and there were no shortage of brands cross-pollinating.
What it all means for the average guy is this: options. More of them than we’ve had in a long, long time. This might just be the most exciting time men’s fashion has known, maybe ever. And in a year when all bets were off, these 25 best dressed men were there to show us how it’s done – leading trends, breaking rules or keeping it classic, their message was the same: wear whatever the hell you want, and do it with a smile on your face.
25. Troye Sivan
You can’t go anywhere at the moment without hearing Troye Sivan’s name echoing off the wall. Not surprising really, it’s been a big year for the South African–born Aussie lad who found himself thrust further into the spotlight thanks to a role opposite Nicole Kidman and Russell Crowe and a Golden Globe nomination for Boy Erased.
The endless photocalls have given him a chance to show us all what he’s made of in the style department, and we like what we see. That being an expert blend of structured tailoring and floaty statement shirts, plenty of colour and just a dash of gender-bending make-up.
24. Tyler The Creator
While his style is pretty out-there, Tyler the Creator actually toned things down in 2019. He’s gone big on knitwear, with cardigans and sleeveless sweaters featuring heavily. There was of course his pastel-laden collaboration with Lacoste, one of the highlights being the pink mohair-style cardigan which he wore to the French Open. It was a big year on the whole though for the Cali native – his 2019 album Igor saw him tour the world, with his alter-ego character breaking out innumerable brightly coloured suits, and that blonde wig.
Take away the wig though, and those suits work surprisingly well. Simply styled, most often with white Dr Martens on the feet, it’s just another example of tailoring’s big comeback. Elsewhere, Tyler continued his take on preppy casual – often dressing like something between Carlton from Fresh Prince and a skatewear Arnold Palmer, and it works. Tyler has always subverted notions of what you expect a rapper to dress like, and that’s why he’s cool.
23. Odell Beckham Jr
American sports and menswear haven’t always co-existed seamlessly. Google ‘NBA Draft 2003’ and witness some of the worst tailoring you’ll ever see. Lebron James, one of the game’s most stylish players today, is dressed as an inflated marshmallow. Odell Beckham Jr was only 11 years old at this time though, and his generation grew up in an altogether different fashion landscape.
By the time the NFL wide receiver was himself drafted in 2014, fashion was already at the forefront of American athlete’s minds. He wore a slim-fit, windowpane suit with a bow tie, pocket square and attention-grabbing diamond watch. Today, things have moved on again and Beckham Jr is one of the league’s more fashion-forward players.
Streetwear-focussed and heavily branded, he even wore a Louis Vuitton x Supreme orthopaedic boot for his injured ankle. He’s also one of the better groomed men in the locker room and, along with James Harden, boasts one of the best beards in North American sports.
22. Mahershala Ali
When Mahershala Ali won his second Oscar at the 2019 awards ceremony, he accepted the gong wearing what is best described as a formal beanie. The fact that he looked elegant and not ridiculous as he did so will tell you plenty about how well this man can dress.
In a year when he also headlined True Detective and landed the role of Blade in the MCU, his style has been all about quiet swagger. He looks as sharp in double denim as he does in red-carpet tailoring, but it’s the latter that got us rubbernecking this year. With micron-accurate cuts, interesting colours and offbeat accessories, he proved that the suit is still a long way from dead.
21. Zac Efron
Zac Efron’s hair had almost as big a year as the man himself. Rocking a shocking white bleach at the start of the year (and somehow pulling it off), Efron had our attention long before his role as serial killer Ted Bundy got everyone talking.
When you’re this annoyingly good-looking, you can afford to take risks with your style, but what we like about the way Efron dresses is that it’s not at all try-hard. He leans on classics like denim jackets, shearling coats and slim-fit two-pieces. There’s a lot of experimentation in menswear right now, and that’s great, but here’s a reminder that for a lot of guys, the old ones are still the best.
20. Henry Golding
Whereas last year saw Henry Golding pique our interest for the first time, this year was Golding’s opportunity to really cement his status as one of the most reliably well-dressed men on the planet, which he took and smashed. Sure, leading man looks and effervescent charm certainly helped, but natural gifts aside, Golding’s dress sense showed an impressive reverence for the importance of making sure that everything fits impeccably.
His numerous forays into tailoring saw all of the classics ticked off with aplomb (read: velvet, black tie) but he also showed he’s a dab hand at more eye-catching looks with bright red and pale grey colour block looks working particularly well.
19. Frank Ocean
Frank Ocean is arguably the most individual dresser on this list. But not in a blatant, over the top way. He knows what he likes, and doesn’t pander to brands or trends. This is a man who quietly showed up to Paris Fashion Week wearing a yellow down jacket from relatively unknown Swiss ski brand Mammut, when everyone else was dressed by the designers whose shows they were attending.
He went to the Met Gala dressed as a bouncer, in all-black Prada, as he worked as a photographer taking candid snaps for Vogue. He drives BMWs from the 1980s while his contemporaries fight over the latest supercars. He wears deadstock vintage Nikes while everyone else rocks Balenciaga.
Most modern celebrities (including many on this list) hire stylists to dress them, which, let’s be honest is cheating. A professional stylist would never advise a client to wear some of the looks Ocean wears, and this is precisely why we rate him so highly. He does his own thing, and this should be celebrated.
18. Eddie Redmayne
The eternally preppy Eddie Redmayne’s style hasn’t changed much in the last five years, and that’s no bad thing. Done well, preppy style is hard to beat, and Redmayne is head boy. From collegiate-inspired outerwear to sharply tailored suits, the Fantastic Beasts star rarely puts a foot wrong, and gives all the credit to his wife. There’s one way to save on hiring a stylist.
17. Rami Malek
Oscar-winner, Bond villain, style hero. It must really suck to be Rami Malek. He might have lived in hoodies during his breakout role in Mr Robot but off-screen, Malek’s style is a lot more polished. He combines inch-perfect tailoring with a few statement touches thqt wouldn’t look out of place in Mick Jagger’s tour wardrobe. Think bold patterned shirts or the occasional velvet jacket.
There’s a certain amount of swagger here but some of the confidence to do it may stem from the fact that he grounds everything he wears with staples like black tailored trousers. That and the fact he’s Rami Malek.
16. Brad Pitt
Here’s a funny thing: Tyler Durden is way more stylish than Brad Pitt. The actor is a fashion icon but when he’s not wearing a tuxedo, Pitt’s look is comfortable and – how shall we put it? – artfully unkempt. It works because a) he’s impossibly good-looking and b) his many stylish roles feed into his megawatt persona.
In spite of all that, he looked bloody good this year, onscreen and off. In Quentin Tarantino’s Once Upon A Time In Hollywood, he wore the hell out of 60s and 70s outfits comprised of double denim, retro T-shirts, leather jackets and Hawaiian shirts. And on the publicity circuit, he flitted between excellent tailoring and defiantly laid-back looks, including flat caps, slouchy trousers and T-shirts worn over long-sleeve tops. Not many people can do that. Brad Pitt can.
15. Nicholas Hoult
Nicholas Hoult’s menswear stock has been steadily on the rise for some years now, but this year it reached its peak. Not surprising, given his ability to pull off coloured tailoring is second to none, from a subtle navy dinner suit to a seventies-inspired blue and yellow look and everything in between.
Far from a one-trick pony, when he’s not suited and booted you’ll often find him going big on texture with a series of killer suede jackets worn over printed shirts and dark denim. There’s something about this boy.
14. Mark Ronson
The release of his new album Late Night Feelings meant that 2019 saw more appearances for Mark Ronson than we’re traditionally accustomed to. As is standard for Ronson, this meant lots of retro-inflected tailoring that stayed far away from the humdrum, it was all brightly coloured, richly textured and always worn with the producer’s trademark insouciance.
In fact, we’d even go as far to say that Ronson was a living, breathing rebuttal to those predicting the demise of tailoring at the hands of streetwear.
13. David Beckham
After some hiccups in the noughties, this decade has seen David Beckham full morph into a seasoned master of menswear and 2019 was testament to Goldenballs’ consistency with (to our knowledge) not one foot put out of place.
We’ve had an endless roster of complementary haircuts and the odd addition to an already sizeable collection of tattoos, and as always Mr Beckham came up smelling of roses. For us Beckham was at his best this year at Wimbledon and it’s no exaggeration to say that all other attendees paled in comparison. But he also excelled – as he always does – in smarter casuals like suede bombers and envelope-pushing tailoring from Dior. He’s still got it.
12. Donald Glover
As one of the world’s most successful multi-hyphenated people, ever, it’s no surprise that Donald Glover’s wardrobe defies neat categorisation, reason or logic. On paper, Glover’s eye-poppingly bold patterned suits, mad flourishes and penchant for going shirtless under tailoring sound like things that render him ineligible for a best dressed man list, but here we are (again) finding ourselves nodding in approval of Glover’s so mad it’s good wardrobe.
11. Shawn Mendes
What had you done by 21? Singer-songwriter Shawn Mendes has had himself three US number-one albums by the age, and all while crafting himself a piece-perfect modern rock and roll style that pays its dues to the past while still feeling fresh today.
Tailoring embellished with ritzy touches are his forte – finished off with a pair of Chelsea boots and rock star bling – while Parisian brands Saint Laurent and The Kooples are among his favourite brands, each possessing the slim-fitting monochrome style that has turned the squeaky clean pop idol into one of menswear’s coolest figures.
10. Pierce Brosnan
To say that Pierce Brosnan (at 66 years of age) was having some sort of second wind would be inaccurate, truth be told he’s been consistently stylish since anyone can remember. Highlights this year include mastering classic suiting, proving that suede bombers look perfectly at home on those past the flushes of youth and making sunglasses worn almost anywhere feel not a jot ostentatious, just achingly cool.
Oh and then there’s the expertly styled shock of silver hair which only adds to Brosnan’s timeless appeal. All in all (another) vintage year for the man formerly known as Bond.
9. Dylan Sprouse
It’s a sweet life Dylan Sprouse leads. Not only has the former Disney child star bagged himself a Victoria’s Secret Angel and the sort of bone structure people go under the scalpel for, but he’s also got one of the finest wardrobes around to boot.
Luxurious knits, chunky leather jackets, electric tailoring – everything screams expensive and well done. Cut also plays a key part – not too slim so as to accentuate his slender frame – it’s a wider fit that harks back to a classier time. He might only be a hot young thing in Hollywood right now, but he’s dressing like a legend.
8. Timothée Chalamet
The fandom is real with Timothée Chalamet. From 60-year-old Ohio mums to teenagers in Korea, there’s something about the Hollywood A-lister that incites frenzy. For some it’s the passionate acting, for others, it’s the cherubic locks. Both are great, but what’s caught our eye the most is his boundary-pushing approach to red carpet dressing.
A muse for high fashion genius Haider Ackermann, the designer has pushed the actor into all manner of space-age tailoring this year, while the star was among the first to sport the infamous Louis Vuitton holster. Sure, both, would look an absolute train wreck on 99.9 percent of men, but they look out-of-this-world on Chalamet. And more importantly, they offer a small glimpse into what men could be wearing ten years from now. Bejewelled holsters at the ready.
7. A$AP Rocky
Hip Hop and clothing have always gone hand-in-hand. But few rappers over the course of time have adopted high fashion with as much vigour as A$AP Rocky. He’s a bold dresser, not afraid of colour, pattern or babushkas, and famously wears everything from Rick Owens to Dior, and Prada to Raf Simons. But then, A$AP Rocky isn’t afraid of anything, not even over-zealous Swedish courts. And this is reflected in the way he wears his clothes.
He has enough braggadocio for an entire nation, and his fearless approach means he exudes confidence – there truly is nothing that he couldn’t pull off and he often looks better in designer gear than the models who wear it down the runway. From oversized pink Loewe suits to tie dye, leather jackets to fur, he can do it all.
6. Chadwick Boseman
Chadwick Boseman knows how to wear a suit. Which is a good job, as when he’s not making box office breaking films, he’s usually on the red carpet promoting them. He makes tailoring fun, and does so through wearing audacious silk jacquard dinner jackets, bold colour suits and favouring unusual cuts. And there’s rarely a tie in sight. Boseman is one of the key figures pushing the boundaries of red carpet tailoring, and for this alone, he deserves a place on this list.
But he’s also adept at dressing down, favouring as he does slim dark denim, sneakers and some form of lightweight jacket on top. He’s never over-styled, and always looks enviably comfortable in what he’s wearing, which is something we can all aspire to.
5. Shia Labeouf
Shia Labeouf is undisputed king of the scumbros and would seem, on the surface at least, to be anti-fashion. Don’t fall for it, he knows what he’s doing. The man has been at the forefront of every ‘uncool’ trend in recent years from the return of grunge to wearing hiking gear in the city.
This year, though, came something very unexpected. Off-duty, he continued the always-knowingly-underdressed thing but on the red carpet he looked like a modern Don Draper. That doesn’t mean slim suits and tie bars, it’s means wearing very modern tailoring in very modern ways, all the while looking like he’s having a fine time at it.
4. Michael B Jordan
Our best-dressed man of 2018 carried his form throughout this year without breaking stride or tweaking the formula (why would you?). The Michael B Jordan winning combo includes fine tonal tailoring and easy-to-copy streetwear looks. No wonder luxury label Coach bagged him as the face.
But here’s something that’s not as easy to steal from the Creed star: he seems to have a Mary Poppins-style bag storing an endless collection of incredible coats.
3. Tom Holland
If the mark of a truly well-dressed man lies in the ability to look great in both formal occasions and when dressed down, Tom Holland nails it every time. Part of the omnipresent Marvel Universe, he’s been everywhere, all year, and on both the publicity tour and the red carpet, the web-slinger didn’t have a thread out of place. We’d happily wear the relaxed check trousers he wore to a Spider-Man fan event in Seoul every damn day. Any chance, Tom?
2. Harry Styles
Harry Styles is best known for his soft-rock sounds and Jagger-esque dance moves, but in recent years the ex-Directioner has also established himself as one of the best-dressed men in the music industry.
Out of the boy-band bubble, these days his wardrobe reflects the switch from pop puppet to viable frontman, with a slew of coloured suits, crushed velvet textures and plenty of IDGAF swag. You can’t bribe the door on your way into a
1. Jake Gyllenhaal
There are always arguments when the FashionBeans team sits down to debate the best-dressed men of the year. That’s unavoidable when menswear is as wonderfully diverse as it is right now. But while we admire the trend-setters and the rule-breakers, dressing like Harry Styles or Tyler the Creator is only really possible if you happen to be Harry Styles or Tyler the Creator. We always end up coming back to someone who wears clothes that are, well, wearable.
For our money, nobody has bridged the worlds of high fashion and everyday style better this year than Jake Gyllenhaal. He’s dabbled with trends (tie-dye, loose tailoring) and fallen back on classics (Harrington jackets, fisherman knits). Occasionally he’ll do something flashy, but more often he’ll abide by the fashion rules that govern everybody, not just Hollywood types with clever stylists.
The colours suit him, the fits are always right and – importantly – he wears the clothes, they don’t wear him. As menswear gets braver and louder, that’s worth remembering.
