You might have formed an unhealthy, borderline toxic relationship with your Havaianas this summer, but the time is now here to pack them away, along with your cozzies, linens and moo-moos. Don’t shoot the messenger, but if the current temperatures are anything to go by, spine-tinglingly cold gusts of wind are here to stay for the foreseeable, which means one thing only: the return of winter fashion.

Ha ha, I hear you laugh: there are only four seasons of the year, of course the final quarter is almost upon us. But that’s precisely what we’ve lacked this year: continuity, predictability.

The stop-start heatwaves and the waves of tropical rain in climes that are usually far from tropical have left us collectively in sartorial dire straits. Never before has dressing been so complicated, such a a 50:50 guessing game to determine which temperature will come up trumps today. 

For those who relish the cosiness and relative stylistic comfort of the colder months, you will rejoice as we crash-bang-wallop our way out of the stifling tunnel of summer; for others, perhaps you’re already pining for your flip-flops and kaftans. Either way, there are silver linings to winter dressing, the sort that give more than they take; you’ve just got to sift through the noise. As Matisse once said: “There are always flowers for those who want to see them,” and that’s never been truer than for transitional dressing – there’s always some aspect of it you’ll enjoy.

Whatever it may look like: winter is here, so be prepared and stock up because, before you know it, we’ll be wading through the bleak mid-winter and god knows what that’ll look like.  

Denim is dead (sort of) and flares are as forgettable as the Posh Cheddar and Pickle baguette you had for lunch for the fourth day in a row. The order from the style set is to keep it cool – which is to say, warm – during winter and embrace cargo pants. Net-a-Porter sold 1,000 pairs of The Frankie Shops’ cult cargo trousers on launch earlier this year, proof of their popularity.

Don’t shy away from their slouchy silhouette; in fact, if you can’t beat them, join them, and try dialling the XXL up a notch with an equally baggy top. They say two wrongs don’t make a right, but in this case they absolutely do. 

Maxi dresses for winter are always a good idea – so shed any connotations you have of them with balmy days and breezy nights. To transition into the winter months, they need a couple of tweaks: reach for long sleeves that will keep potential gusts of seasonal winds at bay; opt for sweeping silhouettes rather than clingy, body-hugging sorts; and wear with layers – always, always wear with layers. If there’s one thing we know for sure it’s that there’s nothing predictable about this weather, so always be prepared. 

This ought to come as no surprise to any eagle-eyed fashion fan, but layering in the depth of winter is crucial to maintaining a patina of prowess. Employ the use of softly padded gilets and light, quilted coats to insulate yourself without compromising on style. Uniqlo’s feted Heat-Tech technology, which it extends to long-sleeved T-shirts, jumpers and other layering essentials, is one of the fashion world’s worst-kept secrets.

Your feet may have become accustomed to the slight fit of your favourite summer sandals, but – as ever – boots are now back in business. The good news this year, however, is that all boots are welcome to this footwear fiesta. Since the return of the Ugg and the Moon Boot to the fore, this has become an open-minded space for any and all boots. All are welcome and all are accepted (but these are a few of our favourites).

How do we categorise the nebulous in-between sartorial requirements of the freezing chaos of winter? Without swearing, let’s just agree that it’s difficult and often accompanied by the sort of emotional black cloud that can be seen from space. The solution to stop-start seasonal dressing can be found in the virtues of waist-up styling, the sort of thing that everyone was doing during the pandemic. Party on the top, business on the bottom.

Images: Getty Images