‘Ignore the weather. Wear shorts with everything’ – how to dress without saying goodbye to summer

<span>Photograph: Miguel Medina/AFP/Getty Images</span>
Photograph: Miguel Medina/AFP/Getty Images

The nights are drawing in already after what, in the UK at least, has been a decidedly lacklustre summer. I, like many others I’m sure, spent most of August – the so-called high summer – wearing clothes I would normally only reach for come October. This has not been the year for light fabrics and loose cuts – even on warmer days there has been the threat of rain. And on the few hot days we had, it hasn’t been the kind of weather you can bank on enough to leave the house without a jacket stashed in a tote.

So here we are, edging into autumn and the time for putting those frothier threads back into a box until next year. But if, like me, you would take a pair of shorts over a puffer jacket any day, perhaps you are feeling wan at the thought of all the dark, damp months to come when it will only be possible to wear boots and dark trousers.

For those of us who consider summer the best season to dress for, how can the most be made of summer clothes when summer is nearly at an end, but the desire to wear summer clothes has not yet been sated? Here, some experts give their advice.

Ignore the weather (sort of)

“The best way to deal with a dreary weather is to ignore it and just wear shorts with everything you’d wear in early autumn,” says stylist Simon Chilvers. “If I had to pick a favourite singular outfit, Desert Island Discs-style, then shorts and jumper or a cardigan would totally be it.” Stylist and directorAradia Crockett agrees. “If you still fancy wearing your summer shorts in a storm, pair them with a pair of ankle wellies for practicality and a Barbour or Rains raincoat and a chunky jumper,” she advises. Similarly, she suggests pairing summer dresses with knits.

But Chilvers goes further; he will also happily wear shorts with a trenchcoat or lightweight parka. “It’s a bit unexpected,” he says, but also sensible, “because even when it’s a bit dreary in the summer it’s not actually that cold, so from a practical standpoint it works on both fronts: you’re dry but not overly hot”.

To take things further, you could do like a shorts-wearing man who was sitting next to me recently at a cafe on a parky day and bring a blanket with you to stop your bare legs from getting too nippy. This kind of dedication to shorts is a joy to see.

Be prepared at parties

Having a blanket about your person is extreme, and of course part of the joy of warmer days is being able to head out for the day without bags stuffed with rugs, but, as we inch into Autumn, it’s best to be pragmatic. But that doesn’t have to mean parking fun in favour of practicality.

The experts agree that a great umbrella is key, but Crockett wonders about mixing it up a little by buying an umbrella in a shade or print to complement your outfit. Chilvers suggests looking to the Jil Sander spring/summer 2023 catwalk for inspiration, “Every single model in that show carried an umbrella,” he says. “And the takeaway here was minimal but not boring.”

Model with umbrella at the Jil Sander spring/summer 2023 catwalk during Milan Fashion Week
A model walks the Jil Sander spring/summer 2023 catwalk during Milan fashion week. Photograph: Pietro S D’Aprano/Getty Images

In addition to a stylish umbrella, Chilvers would add “a good smart shoe and, outfit-wise, something streamlined and unfussy.” For any between-season events that require a tie, he recommends “a knitted tie in a dark colour” that will be a “little cosier in spirit”.

Stylist Lauren Cunningham thinks that tailoring is the answer for parties where the weather is likely to be changeable. “A two-piece trouser and waistcoat set is incredibly stylish yet keeps you much warmer than your typical linen or chiffon dress,” she says. “Or, if you are set on wearing a dress, pull on a blazer for a fashionable yet formal layer. And don’t forget the shoes; knee-high boots can battle almost all weather.” She adds that you can layer under any outfit and no one need know; she recently went to a wedding in a red Rixo midi-dress with leggings hidden underneath; her fellow guests were none the wiser.

Layer up

The experts recommend having layers to hand just in case the weather nosedives. “Jumpers, denim jackets, bucket hats and, this season more than ever, rain macs can all help to make your warm weather wardrobe last a lot longer,” says Chilvers.

“Artfully tie an oversized shirt around your waist with shorts and either a T-shirt or another shirt up top,” he says. “It creates a nice billowing silhouette from the back but doubles as a handy layer.” For short-sleeve shirts he suggests sticking a long-sleeve T-shirt underneath. For women, Crockett says this look works with a poloneck worn beneath a dress. Or that “good old British summer staple”, the classic trench.

Add some zing

“A pop of yellow or a similarly bright colour is also good for making the best out of a dull day,” says Chilvers, who has a yellow baseball cap which, he says, “tops off all outfits with a zing. But you have to be careful that this one slab of colour doesn’t look a bit comedy or too irritatingly jaunty.”

Whatever you choose, he adds, make sure that it isn’t too revolutionary a departure from your usual style. Rather than suddenly wearing a T-shirt and matching shorts the colour of a lime Calippo, for example, “pick things you’d ordinarily wear or things that have been in your wardrobe for a while so they’re a bit worn in”.

Have fun

“ This time of year is for fun pieces that might feel a bit too much for winter,” says Crockett. But having a laugh with getting dressed doesn’t have to mean suddenly wearing tassels and tie-dye, if that isn’t your bag. “My style is generally very minimal – I love beige – but in summer I will wear a gingham or a breton stripe,” says Crockett. “Play around with print, but keep it to one item per outfit.”

Another way to do this is via accessories. “A colourful bag will brighten a more practical outfit if the weather is stormy, but make that the cheerful focus of your outfit and keep the rest simple.” She also enjoys a patterned or broderie anglaise scrunchie.

“Ridiculous as it may sound,” Cunningham says, “I wear sunglasses every day, even if just on top of my head, which allows me to keep the hope of warmer weather alive.”

Put your best foot forward (in socks)

It can be tempting to ban socks until the first leaf falls from your nearest plane tree, but that would be an unnecessary step given the fun that can be had with socks and sandals. “You could team your trusty Birkenstocks with a chunky or fine-gauge sock in both a double-strap style or the clog,” says Crockett. “This works with more feminine dresses, which counter-balance the look. Or you could indeed play into it and team them with grandad cords and a chunky cardigan.”

Fisherman sandals with sporty socks
Feet first … fisherman sandals with sporty socks. Photograph: Image Source/Getty Images

Cunningham is currently enjoying wearing pastel-coloured cashmere socks “with everything – ruched up at the ankles with trainers, with Birkenstock Bostons or poking out of the top of ankle boots”. She hasn’t tried them with sandals yet, “mainly on account of this wet weather making them too soggy”, but, she says, “as soon as it it dries up, I’ll be fashioning them on to my sandal-covered feet”.

And, for even more fun south of the shins, you could try a “disco sock”. Cunningham extolls the virtues of “a Lurex affair with a light sheen that can be worn” on a night out. Proof, if it were needed, that early autumn needn’t be a season for doom or gloom.