The Biggest Style Moments Of 2019


As years go, 2019 has been a turbulent one. We witnessed the devastating consequences of climate change in the Amazon rainforest; we waited in quiet amusement as Cheeto-fingered neckbeards openly conspired to storm Area 51; we saw the first-ever image of an actual black hole, and subsequently hoped it would come to swallow us up whenever politics was on the news.

With another Black Mirror-esque headline hitting the news daily, keeping abreast of the latest and greatest in fashion wasn’t easy. Those who managed, however, will know that the year in menswear proved to be an equally wild ride. Sustainability made its way into haute couture’s upper echelons, legends died (RIP Karl Lagerfeld), new ones were born and (for some unfathomable reason) everyone had their nipples out.

With 2020 just around the corner, it’s time to reflect on the best menswear moments from the last 12 months. From the designers rewriting the rules to the trends worth taking with you into the new year, here we hand out the awards for services to men’s style in 2019.

Most Influential Designer

Christopher Raeburn

In under a decade, Christopher Raeburn has gone from largely-unheard-of freelance pattern cutter to world-renowned sartorial innovator, global creative director of Timberland and leading figure of sustainability in high fashion. His “remake, recycle, reduce” mantra may sound like just another marketing ploy, but believe us when we say that this is a man who truly does practice what he preaches.

For those unfamiliar with the British designer’s work, this year’s collaboration with The North Face is a prime example of what he does best. Using cuttings from old TNF tents, Raeburn created a line of upcycled, co-branded luggage, each bag custom made and completely unique.

It’s a new way of looking at the way in which we consume fashion – reimagining the things we already have, rather than mindlessly buying more – and something we’re sure to be seeing a lot more of as a direct result of Raeburn’s work.

Menswear Icon

Timothée Chalamet

Hot-pink tailoring, a sequin-encrusted chest rig, paint-splattered overalls and even a bowl haircut thrown in for good measure. On paper, Timothée Chalamet’s recent style and grooming choices don’t sound like those of one of 2019’s best dressers, but look at the way he carries it off and you’ll understand.

For some time now, The King star has been helping to redefine and reinvent modern menswear, but it was during this past year that he established himself as one of the key players. Mixing sharp suiting with intricate embroidery, lavish detailing and plenty of colour, there’s rarely been a dull moment when this guy is trotting the red carpet.

Granted, not all of us have the plums necessary to wear an all-over floral-print two-piece and low V-neck to our next formal occasion. Still, where injecting some personality into proceedings is concerned, we can all stand to learn a lot from this Beautiful Boy.

Most Wearable Brand Of The Year


In a retail world hellbent on delivering the latest trends as quickly as possible (at the expense of both the environment and your future self’s ego – thanks, Facebook Memories), Reiss might just be the last bastion of good taste and quality on the high street.

Infinitely reliable, eternally stylish and, while it may be at the upper end of some budgets, capable of producing garments that will last years as opposed to a single season. We’re not the only ones that think so either because in 2019, Ryan Gosling, Tom Holland and Stormzy have all been showing the British label some love.

For timeless designs, flattering cuts and all-round versatility, there’s currently no other brand delivering the goods to this standard at this price point, and you can bet 2020 will be much the same.

Style Move Of The Year

Loosening Up

The year 2019 may have spelt bad news for democracy, the climate and Prince Andrew’s publicist, but was great for our collective circulation. This was the year when skinny fits slimmed down so much that they disappeared entirely, and you no longer had to be a roll-up-smoking skater in a tiny beanie in order to rock a pair of wide-leg trousers.

Baggy pants, wraparound tailoring, boxy shirting and relaxed outerwear; 2019 marked the general loosening up of menswear in the mainstream. Slim-fit is still around, but it’s slowly giving way to a more laid-back look, ushering in a new age in men’s style

Perhaps it’s the latest mutation of the overarching ’90s trend that has been dominating wardrobes for the last couple of years, or maybe men are just sick and tired of wasting five minutes wrestling with their jeans on every morning. Either way, it’s here and it’s not going away, so peel off those drainpipes one last time and give yourself some room to breathe.

Trainer Of The Year

New Balance 990V5

“Worn by supermodels in London and dads in Ohio,” read New Balance’s 2019 ad campaign for the latest sneaker in its much-loved 990 series. And now, as it turns out, basically everyone else, too.

There was no shortage of high-profile trainer releases in 2019 – the Nike x Sacai LDWaffle, the Air ‘Diordan’ and the Adidas LG Spezial to name a few – but in terms of mass appeal, nothing rivalled the success of the 990V5.

The fifth incarnation of the first-ever $100 sneaker, originally released back in 1982, the latest 990 is still something of a status symbol, albeit a very, very comfortable one. To look at, it’s not much. Plain, grey, suede and mesh construction; it’s not exactly crying out for attention, but therein lies its beauty. This is a blank canvas of a shoe; a Stan Smith for the dad-shoe generation.

Worst Trend


We almost can’t believe we’re having to say this, but your nipples are not – repeat, not – the latest must-have fashion accessory. To be fair, you probably already knew that, but some of the world’s leading fashion houses and A-list celebs giving areolas a wholly undeserved amount of airtime obviously didn’t get the memo.

Sheer tops, shirtless tailoring and just straight-up bare chests were everywhere in 2019. Even style icons like Donald Glover were at it, while several designers built whole collections around suits worn bare-chested.

Look, if you’re on the beach or relaxing in the comfort of your own home, fine. Take your shirt off and be at ease. Any other time, put them away, because no Tinder date in their right mind wants to sit across from you at a restaurant trying to eat a pepperoni pizza while your own slices of salami peek out from behind your jacket’s lapels. Just put your tits away, for the love of God.

Luxury Brand Of The Year


Our favourite Dior moment of the last five years has to be when Johnny Depp’s ‘Sauvage’ campaign posters were being defaced so that they read ‘Sausage’ instead. Narrow it down to the last two years, however, and we’d have to say Kim Jones taking the helm as creative director of Dior Man.

Virgil Abloh is often credited with being the man who brought streetwear to the runway, but it’s Jones who made the first real leap. During his time at Louis Vuitton, it was the British designer who masterminded the infamous Supreme collaboration that sent shockwaves through the fashion world. Now, as the creative force behind Dior’s menswear arm, he’s bringing one of the world’s most historic labels back up to speed.

This past year, Dior became relevant again. Yes, there were some bare chests with tailoring, but there were also unprecedented hookups with streetwear legends like KAWS and Shawn Stussy. Jones may have set up the blind date between high fashion and streetwear at LV, but this year at Dior he cemented it as a marriage made in heaven.

Best Collaboration

Aimé Leon Dore x Drake’s

Some things were just made to go together. Strawberries and cream, Bogart and Bacall, beer and karaoke, and, as it would happen, the colourful preppy, streetwear stylings of Aimé Leon Dore and the off-beat, oversized tailoring of Drake’s.

This year’s hottest collaboration was a tale of two cities. On the one side, London’s very own Drake’s: a quirky tailoring and upscale casualwear brand at the cutting edge of the Big Smoke’s menswear scene. On the other, Aimé Leon Dore: the vibrant streetwear label helmed by scene figure Teddy Santis that has had fashion editors’ tongues wagging since it burst into our lives in a flurry of colour back in 2014.

The resulting collection saw ALD reimagine classic Drake’s staples – think unstructured blazers, ties, pleated trousers – and infusing them with a hearty dose of colour, with the odd pair of joggers thrown in for good measure. A masterclass in trans-Atlantic relations.

Best Hair Trend

High & Tight

After several years of messy mops, shoulder-length locks and tousled trims, it was only a matter of time before the pendulum began to swing in the opposite direction. The return of close crops and shaved sides was 2019s biggest tonsorial shift, and with everyone from Ryan Reynolds to the king of hair trends David Beckham getting on board, you can be sure this is a sight of shorter things to come.

The high and tight is the perfect chop for such a busy year. Yes, it looks good, but it’s also a breeze to style, affording even the busiest of men a valuable extra 10-to-15 minutes of pillow time in the morning.

Aside from that, it’s one of the few hairstyle comebacks of recent years that even your nana would like; a far cry from curtains, bowl cuts and whatever that thing was where everyone was dying their hair pink. Smart, sensible and fuss-free.

Biggest Comeback


It’s difficult to determine what will be remembered as the major trends of a decade without the benefit of at least a few years’ hindsight. Still, if we had to put money on it, we’d say that 2010 to 2020 will largely be looked back upon as an era of exposed ankles and sneaker liners.

Proper socks have served society well since the 8th century, but at some point in the last 10 years, men decided we were too good for them. Instead, we opted for ridiculously small ones that left our lower legs exposed to the elements and ourselves open to looking ridiculous whenever we had to take our shoes off at someone else’s house.

This year, however, the tides began to change. Socks crept back up our calves, reminding us all what we’d been missing for so long. From extortionately priced Balenciaga tube socks to classic Nike 3-packs, virtually no ankle was left uncovered. Hey, we all thought we looked cool at the time, but then so did everyone strutting around Carnaby Street in their flares in the ’70s.

Most Wearable Trend

The Great Outdoors

Gore-Tex hardshell, trail runners, hiking boots, fleece jacket, detachable Vibram soles: it might look like a mountaineer’s packing list, but this is actually a rundown of some of the hottest streetwear items from the last 12 months. This was officially the year that functionality went fashion, and if you live somewhere with a climate as wildly unpredictable as the UK, that’s never going to be a bad thing.

The Japanese have known it for a long time, but the rest of the world has finally caught up on the fact that this kind of clobber, when done right, not only looks good but also makes life that little bit more comfortable.

Many of 2019’s most talked-about designers weren’t actually fashion labels at all, but outdoor brands with crossover appeal. Salomon, Hoka One One, Patagonia, Arc’teryx and beyond; the sort of gear that wouldn’t look out of place at a Fashion Week show, but also that your dad might ask to borrow.

Watch Trend Of The Year


In a year obsessed with functionality and utilitarian design, it should come as no shock that 2019’s defining watch trend was something highly practical. Military timepieces came back in force over the course of the last 12 months, giving many men pause for thought when it came to their everyday tickers.

Simple, rugged and stylish, their reemergence offered up a fresh alternative to divers and chronographs when it came to picking a timepiece for day-to-day dealings. Whether it was a simple NATO-strap field watch from Timex, or a heritage reissue from Longines, these armed-forces veterans where everywhere.

As far as trends go, this is one that’s well worth investing in: versatile in terms of styling but also built for the battlefield when it comes to construction. Plus, if you put your money into one of the limited pieces, there’s a good chance you could have a collector’s item on your wrist in a few years time.

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