Some (specifically: Keats) called autumn “the season of mists and mellow fruitfulness”. I call it “the season of boots and bare legs” (I am pretty much the Keats of fashion, yes). Boots and bare legs style Contradiction Dressing is precisely what I like about autumn – it’s your one chance to wear heavy leathers and big, fat woollens with wispy cottons and naked flesh!

I’m sad, of course, about the demise of summer, but there’ll be another one along in eight months or so, and this particular aesthetic transition – the one from heat to the earliest intimations of chill – is definitely the most interesting in terms of how we slip-slide into a new wardrobe.

The urge to flash as much flesh as you can, for as long as the dying embers of your tan endure, clashes excitingly with the escalating pull toward cosiness. The added jeopardy of being caught in sudden torrential rain, adds the kind of sartorial challenge which, if handled imaginatively, can elevate your entire look. Ditto, wind.

Plus, it’s absolutely time to start properly considering options on a new coat, a sentence which should be enough to spark joy in the heart of even the most devoted summer person.

Now.

There are five distinct stages of the autumn fashion transition, each of which kicks in, as September and October progress. Allow me to take you through them.

Level one (early – mid September): boots and bare legs.
Though, technically? I’m kicking this one – 2024 – off, with loafers, socks, and bare shins before graduating onto the boots, because loafers and socks are just dreamily new term at a New England boarding school, all nervy freshness and glimmering possibilities.

The loafers of your dreams are by Hogan, the socks must hit the mid-shin and not be allowed to rumple down (teenagers told me this); and the bare legs are ideally otherwise encased in the same Gucci denim Bermuda denim shorts you’ve been wearing all summer. A plain white tee with a navy Loro Piana cashmere crew neck slung around your neck Just In Case (ugh, so chic!), and you’ve achieved level one autumn!

Level two (mid September): Actual boots and bare legs
As above, but switch the loafers for high, black boots; ie Chanel’s block heel calfskin.

Level three (mid-to-late September): an evening-y maxi dress (but for day), a chunky blazer and trainers

So, when I talk about the concept of Contradiction Dressing, I mean, in terms of occasion, as well as everything else. I am a longstanding fan of evening wear worn in the day. Why save the most glamorous, most fun, sexiest elements of your wardrobe for nighttime; for ‘best’? Seriously.

Take this exquisite ruffled Burberry dress in olive brown paisley print (aka autumn, distilled into a single colourway and pattern), for example; take the whole glitzy energy down a notch with a Bruno Cucinelli twill blazer (ref: Love Story/ new term at a New England boarding school again), add a Prada combat boot, a top note of bedazzlement, in the form of Hermès’ Farandole pendant, and huzzah! Fashion huzzah, which is The Great Huzzah!

Level four (late September, early October): Yes, but – what to do about the rain?
Easy! Simply revert to bare legs and boots – autumn, level two – but add a raincoat! Prada’s, for example, with the drawstring waist and the logo, which is both practical and outstandingly chic; bonus points for having distinct undertones of Oasis revival.

Level five (October onwards. Winter in earnest): A jacket of substance, a dramatic coat and a bobble hat.

Sure, the cold is setting in, and the nights are very dark and very long BUT, plus-side!: All you really have to concern yourself with right now fashion-wise, is outerwear because it’s too chilly to expose any lesser layers to the wider world. Jackets are, by definition, cooler than coats – not sure why, I don’t make the rules, probably something to do with James Dean? It generally is – and the coolest of them all is clearly Balenciaga’s shearling hoodie. 

Coats can theoretically sway Paddington and cute BUT I am very much of the opinion that no opportunity to invoke maximum outerwear dramatics should be passed up. Drama in the shoulders, drama in the lapels, intermingled with the kind of sexiness only ever achieved through menswear-inspired detailing, my friends! Gucci’s wool mohair overcoat in this exquisite greeny gold will see you right. Top off with a Louis Vuitton bobbled beanie, which whispers “apres-ski” to anyone who cares listen.

POLLY VERNON IS A FEATURES WRITER, AUTHOR AND COLUMNIST. SHE HAS CONTRIBUTED TO THE TIMES, THE OBSERVER, THE GUARDIAN, GRAZIA AND MORE. HER DEBUT BOOK, HOT FEMINIST, WAS RELEASED IN 2015.