I swore I’d never wear these four fashion items but I’m now embracing them in midlife

Sarah Bailey
Two of the pieces Sarah Bailey never thought she'd wear: a mini skirt (left) and jumpsuit (right) - Andrew Crowley

I never expected to have a fashion epiphany while playing tennis with my sons, but strangely enough I did. On holiday in France this summer (in boiling temperatures, remember them?), it happened to transpire that thwacking a ball across a rather battered village court every day was an activity that the whole family could enjoy without too many McEnroe-esque tantrums. My only problem was my clothing: my gym leggings felt unbearably hot and encasing; boho holiday dresses billowed all over the place. Neither option had any pockets. “Why can’t you wear shorts?” asked my youngest with exasperation.

As my riposte started to form on my tongue – because I don’t wear shorts. I’m a midlife woman with a complex about my legs. I haven’t worn shorts for 40 years – I hesitated. What kind of an answer was that? Lame (as my sons would say). And so the next day, I decided that I would wear shorts, albeit my pyjama shorts, as they were the only ones I owned (before you faint, they happen to be made from a rather smart ticking-striped fabric). I styled them with an oversized man’s Etro shirt and, to my surprise, I felt carefree and uninhibited. Even more astonishingly, I actually liked what I saw in the mirror (and I’m quite sure I went on to hit the ball with a little more panache).

But in fact, something else happened to me that day... As the mental block about what I could/couldn’t wear started to shift, I began to feel a fluttery excitement about what I might try next. People often think that I am a bold dresser – because I love colour and print – but in truth my approach to silhouette errs toward the conservative: midi and A-line, with a side order of not-particularly-adventurous denim.

But if I could make my peace with shorts (of all things!), what other previously dismissed items might be worth giving a second chance? Ankle-flapping corduroys? Jumpsuits? “A mini?” suggested my editor Bethan, as I explained the sartorial no-nos I was planning to interrogate. My resolve withered slightly at the word “mini”, but in the spirit of adventure, I agreed.

Finding my perfect shorts

To begin with, I know the PJ shorts revelation demands further investigation. Holiday outfits are one thing, but can I actually wear shorts in my real life, in the city, in autumn? Looking around me, I’ve noticed younger friends wearing sleek, black leather Bermudas to power meetings and date nights to great effect. And as for the runway inspiration? Shorts are everywhere. Take the opening look for Sabato De Sarno’s debut collection for Gucci recently – a tailored mannish coat paired with high-heeled loafers and teeny-tiny black tailored shorts: chic as hell, but frankly also a bit daunting…

Sarah Bailey
Sarah Bailey

Raey Denim shorts, £125, Matches Fashion; Cotton shirt, £69.95, Massimo Dutti; Leather loafers, £199, All Saints; Pearl and gold vermeil earrings, £120, Deborah Blyth

I decided to seek the advice of Tess Wright, fashion stylist and costume designer, who has worked with Alex Jones, Ellie Taylor, Sheridan Smith and Mary Berry, and who regularly puts her clients in cute short looks. “Stepping outside your comfort zone and trying new silhouettes can be liberating and can unleash a whole new dimension to your wardrobe you never even considered,” says Tess. “Take the shorts dilemma for example. You say you have just discovered PJ shorts with a man’s shirt and loved it. The reasons I can imagine are that the shorts are comfortable to wear, they show leg, but not too much thigh. The oversize shirt over the shorts gives you a fab trapeze silhouette, so you don’t have to worry about waistbands, muffin tops or French tucks…You just chuck it on and it looks great.”

Spurred on by Tess’s enthusiasm, I start scouting for likely pairs online, entering improbable search terms like “long shorts to wear in winter”. One of the multi-brand sites with the best selection is Matches, and specifically their own label Raey, which encapsulates a seasonless approach to wardrobe-building and a borrowed-from-the boys attitude, which is what I am looking for.

I speak to Raey’s creative director Rachael Proud about my quest to wear shorts in midlife (and how it all began with me envying my sons’ soft, easy streetwear shorts ). “Oh my goodness, [this] is exactly the founding principles of Raey! Why should women feel tucked-up and formal all the time, even at work?” So how does Rachael style shorts to look both cool, but also grown-up? “With some gold jewellery, big gold hoop earrings and high-top trainers or flat slides. Or, we can go back to the 1990s and wear them with a pair of heels… A key styling tip I have is no tights under shorts. There aren’t many rules I stick to, but that is one!”

In the studio, I try on a pair of Raey “jorts” (that’s “jeans shorts” to you and me, the opposite of skimpy Daisy Dukes), picking out a voluminous pussybow shirt to go with them, which gives the trapeze effect Tess was talking about. I also stick to the no-tights advice, which feels less scary when I switch out a pair of black loafers for an oxblood option (black is a bit harsh against my pasty legs). The verdict? This outfit feels very different for me, but also like a serotonin boost – a tiny bit mischievous and rather empowering.

Corduroy trouser

Next up: corduroy ankle flappers, another one of my love/hate/not for me sartorial blocks. In truth, I have often been tempted by the retro cosiness and Wes Anderson associations of corduroys over the years, but always write them off, telling myself that you have to be a rangy female version of Jarvis Cocker to carry them off. Corduroy is too bulky! hollers my inner voice.

Sarah Bailey
Sarah Bailey

Cord blouse, £180, Wyse; Corduroy trousers, £39.90, Uniqlo; T-bar shoes, £165, Esska; Pearl and gold plated earrings, £290, Antonia Guise

In the studio, I pick out a pair of wide pants from Clare Waight Keller’s Uniqlo: C collab (the butterscotch fabric is remarkably similar to that of Miu Miu’s cord pants, which I admit I recce’d in Selfridges the other day). The Uniqlo: C pants are soft, swishy and exceptionally easy to wear. The game-changer factor here being that they are cut like flat-fronted trousers, rather than jeans, meaning I get no nightmarish teenage flashbacks of sausaging myself into rigid, jumbo-cord, straight legs.

Styling-wise, I had intended to pair the cords with a fairisle sweater vest (you are spared this sight, dear reader;  frankly I looked like Tom in The Good Life). Instead, the Telegraph team recommend a flouncy, embroidered, needlecord blouse from Wyse, which is much more feminine and uplifting, and successfully counters any drab 1970s geography teacher connotations. Another resounding win.

The mini skirt

And so to minis…. Despite my stubbornly ingrained ideas about appropriate skirt lengths for pear-shaped bodies, minis have been on my mind ever since I reread Mary Quant’s autobiography earlier this year, reminding myself what a brilliantly bold and sexy rule-breaker she was. I also met Rachel Peru, the model, midlife influencer and founder of the Liberté-Free to Be podcast, at a talk I gave about Mary Quant at Goodwood Revival. Rachel was sitting front row, wearing a form-fitting, above-the-knee Pucci shift dress and fondant pink tights: living proof that you don’t need to be built like Twiggy to look like an absolute goddess in a mini.

Sarah Bailey
Sarah Bailey

Wool jumper, £245, Herd; Checked skirt, £219, Sandro; Leather loafers, £375, Russell & Bromley; Gold plated earrings, £290, Deborah Blyth

Later, when Rachel and I exchange emails, she tells me that despite loving dressing up as a child, she lost confidence in her 20s and 30s and had to work to regain “a healthier body acceptance”. She explains she actually dreaded shopping: “ I could never find anything that worked for me, I lost that sense of fun… Starting a new career as a model at 46 also helped me, working with different stylists opened my mind to outfits I would never have looked at.”

I do my best to channel Rachel’s beautiful body acceptance as I look through the mini skirt options in the studio. I’m drawn to a slightly punky Sandro kilt in a witty, menswear tweed, but on the rail it looks very mini indeed. Tona, the Telegraph’s style director, explains that where the skirt sits will determine how short it looks on the leg, so I will never actually know unless I try it on. Wise words. It turns out that the Sandro kilt is low-slung and slouchy, it’s hem landing just above my knee… and I love it. I add a glorious pair of pearl-studded loafers, instead of defaulting to heels, which feels nicely laid-back. Tona talks me into pulling the look together with 40 denier tights (I’ve been a 90 denier die-hard for decades and am thoroughly bored of their matte dullness). It’s yet another reminder of how energising it can be to let someone shake up your ideas.

The jumpsuit

Challenge number four: jumpsuits. In the interests of transparency, I confess I have worn a jumpsuit before – to a music festival (but as almost everyone else seemed to be dressed in a bra top and mermaid tail that day, I’m not sure that really counts). What I want to know is can I pull off a jumpsuit to the office, or for an evening out, without looking like I’ve dressed for a Challenge Anneka costume party.

One woman who knows is Sarah Clark, stylist and founder of Douceur, who has collaborated on her own line of jumpsuits with By Iris. “A jumpsuit and heels (specifically a high metallic sandal) is always my evening go-to look and it has never failed me yet,” Sarah tells me. “The key to making a jumpsuit work is, without doubt, the proportions, which of course will vary hugely from person to person, depending on body type/shape, height and preference. As tedious as it is, if you’re a jumpsuit virgin I would recommend trying on a few (as many as possible ideally), and in various sizes if you’re looking for The One.”

Sarah Bailey
Sarah Bailey

ba&sh Denim jumpsuit, £300, Matches Fashion; Mary Jane shoes, £160, Esska; Pearl and gold vermeil earrings, £120, Deborah Blyth

After rifling through the options with the help of the Telegraph team, I settle for a denim option by ba&sh, which somehow combines a bit of Farrah Fawcett sex appeal, with a Rosie the Riveter ready-for-anything vibe. Adding a metallic high-heel Mary Jane injects exactly that counter-intuitive fizz I love when wearing a utilitarian staple. Desk-to-cocktails? I am ready for you.

In conclusion, I feel exhilarated by all the outfits I’ve put together (with the help of my friends) for my never-will-I-ever challenge. Reflecting on whether there is a common factor that these particular pieces – which I have avoided most of my adult life, but now have a hankering for – possess: I guess it’s all about a freedom of movement, feeling a sense of ease with my body and embracing a lighter, less formal mood. I think about something Rachel said to me about liberating her mind and starting to truly enjoy experimenting with fashion in her 40s: “I started to focus on how clothes make me feel, rather than worrying about the so-called ‘rules’ older women are so often told.”

Hear, hear! After all, who wants to be stuck in midis forever? Bring on the midlife minis!