Buckle in, boys. 

Because from now until the frolics climax on New Year’s Eve, we are about to enter the most socially exacting period of the calendar – the Christmas season. Fundamental festive landmarks apart, there is a plethora of dressed-up occasions ahead that a Sloane Street-adjacent gent can be expected to rise to. 

Probable-possibles might include a concert at Cadogan Hall, a recital at Holy Trinity, a play at the Royal Court, a winter wedding at Chelsea Town Hall (where my parents got hitched), a lads night out at The Carlton Tower Jumeirah bar or The Cod (a short stroll from the Street), and inevitably a work party (or several) in those benighted hinterlands beyond Hyde Park.

Which all places significant pressure on the wardrobe. So here’s a straightforward solution – rather than ask yourself ‘what am I going to wear tonight?’, why not wonder ‘who am I going to be tonight?’.

Here, we suggest three versatile personas to ‘wear’ – plus the garments to assemble them – that should cover every eventuality.

This is the classic English gent’s uniform with a twist. For, instead of being specifically English, we’re going for something tastefully transnational – just like Sloane Street these days. 

Think elevated impeccable tailoring from Hackett, sleekly silhouetted outerwear from Brunello Cucinelli, classical but slyly unconventional shirting, ties and pocket squares from Hermès. All of this should be built above foundational footwear – look no further than Berluti. Add an unassuming Cartier Tank watch plus complementary cufflinks to the ensemble, then serve garnished by a Peter Jones-sourced Paul Smith umbrella to twirl as you pootle respectably from pillar to post.

SW1 and its environs represent a style ecosystem of many parts – some of which are simply unsuited for suiting. If you are Royal Courting and then supping nearby or venturing to Mayfair to frolic with the hedgies at The Guinea Grill, it’s time to get “casual”. Just don’t mistake “dressing down” for going downmarket. 

So, starting from the top, might we suggest a genteel baseball cap (best sourced from Loro Piana) and a minimalist-luxe bomber (Tom Ford) over a fine-gauge knit and plain T shirt (try Giorgio Armani). 

If you are of the gilet persuasion, Façonnable is your friend. Complete the look with a tapered trouser – maybe even some jeans – from Rag & Bone and an elevated sneaker from Hogan or Tod’s and, hey presto, you are a paragon of exceptionally lovely informal dressing. Chuck on a Casio from Rag & Bone’s collaboration (if you can get your hands on one, that is), and your casual camouflage is complete.

The Brits tend to be a little judgmental about ostentation – put it down to intellectual snobbery, which is all we’ve got these days – but sometimes, who cares? To do justice to a full-tilt party night, you want to dress like a sybarite – and maybe even flirt with capital-F fashion. 

There are so many options here, but Versace, Gucci and Dolce & Gabbana are paradigms of party attire. Gucci’s aesthetic is slightly ironic, with 1970s-tinged, pattern-heavy pieces that you can imagine in a Wes Anderson flick. Dolce and Versace, by contrast, are unapologetically dedicated to pleasure-seekers – think lush prints, sensual cuts, and molto-masculine silhouettes that lean either towards streetwear or the houses’ tailoring traditions. 

Slightly less expansively lavish, but built for creatures of the night nonetheless, Saint Laurent is an excellent source of moonlighting rockstar attire: if you are of the leather-jacket-and-denim persuasion, then it ought to be your destination of choice. 

All of these houses offer looks that are highly amenable to glinting accessories, so this is the time to bust out your Bulgari jewellery. And an Omega Moonwatch will keep you up to speed with just how late it is – should you care to know.

Luke Leitch is a fashion editor who has contributed to Vogue, British GQ, Financial Times, The Wall Street Journal, and many more.