This month, Gagosian Gallery director and curator Mr Antwaun Sargent – easily one of the most stylish men in New York City (and a one-time star of MR PORTER) – provided a lesson in non-stuffy suiting for the party season. Pictured here at the Hirshhorn New York Gala, he opted for a classic black two-piece and loafers, which on a somewhat less confident dresser might have looked rather unnoteworthy and slipped entirely under our radar. The magic lies in his choice of a textured, off-white beanie – a Sargent signature – which lends an instant devil-may-care attitude to the more tailored pieces and is an unconventional styling tip worth stealing this chilly season. Elsewhere, his crafty, intricately detailed shirt with a subtle pop of colour reads as fresh and effortless against the classic gear and exudes just the right amount of personality.

We’re well known for giving kudos to the whole gamut of well-dressed actors. But, until now, Mr Tom Blythe has been a blind spot for us. The British actor makes a name for himself thanks to his performance in The Hunger Games: The Ballad Of Songbirds And Snakes, but it’s his press tour style choices that have particularly impressed us. And like the on-screen icons Messrs Marlon Brando and Steve McQueen, the budding film star proves the leather biker jacket is still an essential item for a leading man. Consider this the first of many times the young star will grace both the big screen and our best-dressed list.

Streetstyle photographer and costume designer Mr Mordechai Rubinstein is known – and loved – for his unusual fashion sense. And this outfit is a fantastic representation of why. Let’s start from the bottom: gorgeous suede boots, 2000s-era whiskered denim, a Polo Sport hoodie and a wool plaid blazer. On paper this doesn’t sound like a winner, but the sum, as they say, is greater than its parts, don’t you agree?

Avid watchers of the rise-and-fall of menswear trends will have noticed that slim-fit clothing has largely fallen out of fashion lately, as the pendulum has swung towards wider, baggier fits. But, as with all trends, it’s advisable to take this with a pinch of salt. Men of taller, leaner proportions should look towards the 6ft Mr Omari Douglas, whose neat, closely-tailored suit perfectly complements his stature. A heeled ankle boot also smartly extends the line his silhouette. It’s a trick worth stealing, no matter how tall you are.

If there’s one thing we know about Tyler, the Creator, it’s that he is a man who is not afraid of earflaps. And, if there’s another thing we know about him, it’s that he likes his loafers and Derby shoes. When he stepped out in London earlier this month, he swapped the ushanka for a slightly more reserved sheepskin trapper’s hat and chose a pair of chocolate leather Paraboots to match. A faux fur-trimmed teal bomber, crisp white tee and cream slacks complete the rapper’s trademark preppy RnB style.

The Northrop Grumman B-2 Spirit, better known as the Stealth Bomber, is a strategic subsonic flying wing designed to evade radar, infrared and radio frequency detection. That said, if you rocked up to the screening of Mr Dan Levy’s new series for Netflix in one, chances are, someone would notice. Likewise, the outfit chosen by filmmaker and photographer Mr Simon Frederick to attend said event may elude some, but caught our eye. We’re talking about the deployment of some serious utilitarian hardware in seriously dark tones – layers of black and midnight blues, possibly rendered in mil-spec anti-reflective paint. What stands out, though, is the robust sand-toned boots, which is something the USAF should also try workshopping.

A tailored suit in a black and white palette is a classic for a reason, but it can also read as boring or uninspired. Here, actor Mr Joe Alwyn shows us how to jazz up a very simple look by swapping his suit jacket for a double-breasted leather version. His white shirt also appears standard enough, until you notice the French cuffs at his wrist, adding a subtle, dressy detail to his outfit. The heeled black boots and metallic bracelet are just the perfect finishing touches for a modern take on a classic.