“Don’t you love New York in the fall? It makes me want to buy school supplies. I would send you a bouquet of newly sharpened pencils if I knew your name and address.” So goes the line in Ms Nora Ephron’s script for You’ve Got Mail. But while Ms Meg Ryan is waxing lyrical about stationery, it is for the rest of us to remember that September can be a tricky month. Summer fun is largely over (boo!) and the weather ricochets between the kind of misty rain that gets you wet without noticing, occasional torrential downpours and sudden, unexpected bouts of sun that inspire the frenzied shedding of layers before perspiration can take hold.

The question is, what should you wear at such a time? As fans of a sartorial challenge, we’ve picked out some of our favourite versatile items that will make the seasonal transition that little bit smoother.

To me, September equates to sweatshirt season. It’s not quite down jacket weather yet (phew!), but it can get just cool enough that a T-shirt won’t do. This year, I’m opting for this piece by AMI. It’s subtle enough to pair with basically anything – shorts, denim, trousers – but the logo applique heart gives it that little extra pop.

Just because we’re edging towards the colder months doesn’t mean you have to jettison bright prints and colours entirely. Top of my Wish List this autumn is this satin bomber jacket by AMIRI. The Woodstock-inspired, rainbow-hued, tie-dye print combined with the fluid, silk-blend fabric of this jacket will make me hard to miss. I’ll style it with charcoal Saman Amel wide-leg trousers and a pair of Maison Margiela boots.

This autumn, I’d love to imagine myself retiring the jaunty little silk scarf and Breton shirt in which I’ve spent my summer in favour of a safari jacket and a beefier, patchwork scarf. If only. Maybe wearing this Missoni number at home with my PJs can help me pretend. 

A pair of slip-on Vans might see you through summer. But you can’t kick leaves or splash through puddles in white canvas sneakers. A sure-footed upgrade on the standard runner, trail running shoes are built to take on wet, unruly terrain and really come into their own once the weather shifts gears. The latest iteration in Nike’s Terra Kiger line employs the brand’s React hardware for a smooth ride, even on the roughest of surfaces. (I mean, have you seen the uneven paving slabs of south London?)

When the UK isn’t sure if it’s summer or autumn, it tends to stress me out. Am I meant to wear a hoodie and something waterproof, or a T-shirt and jersey cut-offs (my preferred look)? I think this lightweight jacket by Nicholas Daley will calm my nerves somewhat. Worn over any outfit, or just by itself with some tailored trousers, I’m ready for anything.