How to master transitional dressing: 17 clever buys for autumn and beyond

Trench coats, maxi dresses and Meg Ryan-inspired layers – here’s what to wear as an Indian summer vies with nippy nights

Often regarded as a sartorial no man’s land, the shoulder season connects the carefree, bare-armed days of summer with the wrapped-up neck of winter. It can be a tricky time to get dressed, switching between low-20s summer heat and sudden autumn chills – and the rain doesn’t help.

This is the season when layers are your friend, and a few choice ones can help make sure you don’t feel like Joey in Friends wearing the whole of Chandler’s wardrobe, or in need of Mary Poppins’ bottomless bag to cart them around when the sun comes out.

***

Transitional dressing made easy

***

A trench

Asymmetric short trench

£65 at M&S

No transitional dressing list is complete without a trench. In recent years, brands have been putting their own twist on this wardrobe classic, such as this asymmetric short design from Marks & Spencer. Perfect for wearing with jeans or a skirt, and not a bit boring.

***

***

Rugby shirt

Striped cotton rugby shirt

£130 at Gant £130 at Next

Thanks to their thick cotton, long sleeves and “poppable” collars, traditional rugby shirts are a great choice at this time of year. Enjoying something of a renaissance at the moment, Gant is a brand that knows how to make a rugby shirt, and this one is bold and bright. If you fancy something vintage or secondhand at a lower cost, Depop has plenty from Ralph Lauren, Gant, Tommy Hilfiger and more.

***

Lightly padded jacket

Corduroy jacket with pockets

£159 at Arket £159 at H&M

I can almost hear the imminent rustling of the leaves when I look at this preppy autumnal corduroy jacket – brought up to date with a quilted design and large pockets. An oversized fit would work with a layer or two underneath for colder weather, but it’s also light enough to fling over a T-shirt in shoulder season.

***

Suede tote

Suede slouch bag

£195 at Jigsaw £195 at John Lewis

If you fancy giving your raffia and straw summer bags a well-earned break – or perhaps the changeable weather means you need something a little less likely to disintegrate in rain – then a suede tote is a smart solution. Just make sure to spray it with fabric protector first; it’s bound to drizzle on its first trip out.

***

A rain poncho

Smiley rain poncho

£69 at Rainkiss

I recently spent one of the soggiest weekends of my life at End of the Road festival, and these kinds of ponchos were everywhere. It struck me as a smart choice, and ideal for this time of year, when downpours seem to be frequent and quite dramatic. You can pop them over everything, including your bag, and stay dry enough that when the sun shines again, you can simply whip it off and pretend it never happened. Great for cycling, too.

***

Knit polo

Merino wool polo top

£75 at Cos £75 at H&M

This is ideal for channelling Meg Ryan in You’ve Got Mail, whose shoulder-season wardrobe is a thing of beauty. She’d probably pair this with a pleated skirt and sensible shoes, but it would also look great with track pants, cargo trousers or jeans on the weekend, or pinstripe trousers to add a bit of workday direction. I’d also team this with shorts – Adidas three-stripes, say – on a still-warm day.

***

A party frock, with long sleeves

Long-sleeve mini dress

£105 at Damson Madder £105 at Anthropologie

Just because summer’s over, it doesn’t mean the party needs to be. But it might mean long sleeves are a good idea. This frock is made from flattering shirred organic cotton and has a pleasing 80s prom energy.

***

Merino wool and silk vest

Sleeveless wool vest

£35 at Cambridge Baby £24.68 at Amazon

This is the kind of invaluable layer that can make much of your summer wardrobe wearable for a few weeks longer than it otherwise might be. Made from merino wool and silk, it’s soft and should be wearable next to the skin for all but those most sensitive to woolly textures. Be warned that this style runs long, so you’ll probably need to tuck it in.

***

Silk-cotton cardigan

Button-down silk-cotton cardigan

£120 at Rise & Fall

Elegant with a single button done at the top; practical worn entirely open with a T-shirt; or crisp and simple worn buttoned up with nothing underneath, this silk and cotton cardigan is a versatile beast. While I can’t say the “drift” or “buttermilk” colours fill me with joy, in red, it could spice up even the dreariest of days.

***

Maxidress

Denim maxidress

£135 at Aligne

A sleeveless dress with a baggy cardigan is a classic shoulder-season combination. Wear with socks and loafers for preppy autumn vibes, or trainers for something more laid-back. If you want a more streamlined silhouette, ditch the cardigan and layer something tight-fitting underneath – such as this lightweight long-sleeved top from Cos.

***

The perfect ‘shoulder season’ shirt

£95 at Cos £95 at H&M

Flannel, checked, and, at a squint, a lot like the plaid shirt Kate Moss made aspirational in 2023, this is the ideal shoulder-season piece. A plain white vest underneath it, a la Kate, would make for a classic weekend top-half paired with jeans.

***

Layered T-shirt

Layered raglan T-shirt

£75 at Glassworks

If you find sartorial colour combinations slightly bewildering, a pre-layered garment will take the work out of your hands. This gently fitted T-shirt is a great example, blending summery sky blue with a more autumnal chocolate brown.

***

Warm socks

Wool boot socks

£22 at Falke

Heattech socks

£7.90 at Uniqlo

It’s not time for tights just yet (once you put them on, it’s hard to go back), so try bridging the gap with a pair of warm socks instead. These Falke ones in beige and grey are wholesome in all the right ways; I love the blue too. Perfect with loafers, mules or Mary Janes. Otherwise, a pair of Heattech ones should keep feet toasty on chillier days – Uniqlo is the don of the genre.

***

A tank top

Merino wool tank top

£155 at Toast

A wool tank can seem like a real flash-in-the-pan garment: too hot for summer, too chilly for autumn. But that needn’t be the case if you wear it flexibly either over a top, or under a chunky cardigan. For this time of year, a T-shirt or blouse underneath should keep you from overheating.

An aside: the website of the very lovely, very pricey Spanish knitwear brand Babaà is often a brilliant source of knitwear layering inspiration.

***

Back-to-school shoes

Leather Weejuns shoes

£100 at GH Bass

After a summer in flimsy sandals that make your feet slap the pavement, it can be tempting to leap straight for a firm, chunky boot when the weather gets cooler. As with tights, it’s best to resist for a bit longer. These reduced Weejuns shoes from heritage brand GH Bass have a galvanising back-to-school energy. Wear with slubby socks and skirts, or crisp white cotton socks and blue denim to channel James Dean, apparently a Weejuns fan himself.

***

A gilet

Quilted cotton gilet

£100 at Folk

Gilets can sometimes lean a little Badminton Horse Trials, but this relaxed one from Folk fights for its place in the shoulder-season wardrobe. Its beautiful, deep green is an invitation to have fun with colour combinations. It will also team well with a scarf if you need an extra bit of warmth.

***

Ellie Violet Bramley is a writer who has been delving into style and what it means for nearly a decade – mostly for the Guardian’s fashion desk