I never expected to experience a fashion epiphany while playing tennis with my sons, but strangely enough, I did. While on holiday in France this summer (in boiling temperatures, remember those?), it turns out that hitting a ball every day on a well-worn village pitch is an activity the whole family can enjoy without the McEnroe-like tantrums. My only problem was my clothes: my gym tights were unbearably warm and tight; boho holiday dresses were floating everywhere. There were no pockets in either option. “Why can’t you wear it? shorts?” my youngest asked in exasperation.
As my answer begins to form on my tongue – Because I don’t wear shorts. I’m a middle-aged woman with a complex about my legs. I haven’t worn shorts for 40 years – I hesitated. What kind of answer was that? Lame (as my sons say). And so the next day I decided to do this: to want Wear shorts, even if they were my pajama shorts, that’s all I had (before I faint, they’re made of a striped fabric that ticks pretty smart). I wore them with an oversized Etro shirt and felt surprisingly carefree and reserved. Even more surprising, I actually liked what I saw in the mirror (and I’m pretty sure I kept hitting the ball with a little more flourish).
But actually something else happened to me that day… As the mental blockade of what I could and couldn’t wear began to shift, I began to feel a floating excitement about what I might try next. People often think I’m a bold dresser – because I love colors and prints – but in reality my approach to the silhouette tends towards a conservative one: midi and A-cut, with denim on the sides that aren’t particularly adventurous.
But if I could make peace shorts (first of all!), what other previously overlooked items might be worth giving a second chance? Corduroys that hug the ankles? Overalls? “Mini?” While explaining the sartorial no-nos I was planning to query, my editor recommended Bethan. When I heard the word “mini” my resolve waned a little, but in the spirit of adventure I accepted.
Finding my perfect shorts
First of all, I know the pajama shorts reveal requires more investigation. Vacation clothes are one thing, but in real life, in the city, can I really wear shorts in the fall? As I looked around, I noticed my young friends wearing stylish black leather Bermudas to great effect at meetings and date nights. As for runway inspiration? Shorts are everywhere. Take a look at the opening look of Sabato De Sarno’s recent debut collection for Gucci: a tailored masculine jacket paired with high-heeled loafers and teeny black tailored shorts: very chic but frankly a bit intimidating…
Raey Denim shorts, £125, Matches Fashion; Cotton shirt, £69.95, Massimo Dutti; Leather loafers, £199, All Saints; Pearl and gold gezil earrings, £120, Deborah Blyth
I decided to seek the advice of fashion stylist and costume designer Tess Wright, who has worked with Alex Jones, Ellie Taylor, Sheridan Smith and Mary Berry and regularly delivers cute short looks to her clients. “Stepping out of your comfort zone and trying new silhouettes can be liberating and add a whole new dimension to your wardrobe that you never thought of,” says Tess. “Take the shorts dilemma for example. You say that you have just discovered the men’s T-shirt and pajama shorts and you like them very much. The reasons I can guess are that the shorts are comfortable to wear, show legs but not too much hips. The oversized shirt over shorts gives you a gorgeous trapeze silhouette so you don’t have to worry about waistbands, muffin tops, or French pleats… You just throw them on and they look great.”
Inspired by Tess’ enthusiasm, I begin scouring the internet for possible pairs, entering unlikely search terms like “long shorts for winter.” One of the multi-brand sites with the best selection is Matches and specifically their own label Raey, which epitomizes a seasonless approach to wardrobe making and an attitude borrowed from men, which is what I’m looking for.
I talk to Raey’s creative director, Rachael Proud, about my quest to wear shorts in middle age (and how it all started with me being jealous of my sons’ soft, comfortable streetwear shorts). “My god, [this] These are exactly Raey’s founding principles! Why should women always feel stuck and formal, even at work?” So how do Rachael-style shorts make you look both cool and grown-up? “With some gold jewelry, big gold hoop earrings, and high-top sneakers or flats. Or look 1990s.” “We can go back and wear it with heels… One of the most important style tips for me is not to wear tights under shorts. There aren’t many rules I follow, but this is one!”
In the studio, I try on a pair of Raey “jorts” (that’s “denim shorts” to you and me, the exact opposite of short Daisy Dukes) and choose a matching, baggy pussy-bow shirt that gives a trapeze effect. He was talking about Tess. I’m also sticking to the advice of not wearing tights, which feels less intimidating when I swap out a pair of black loafers for an ox-blooded option (black feels a little harsh on my pale legs). Decision? This outfit looks very different to me, but it’s also like a serotonin boost; A little mischievous and very empowering.
Corduroys
Next up: velvet ankle flaps, another one of those sartorial blocks I love/hate/not for me. In fact, over the years I’ve often been tempted by the retro comfort and Wes Anderson associations of velvet fabrics, but I always write them off and tell myself that I’d have to be the skinny female version of Jarvis Cocker to pull them off. Velvet is too bulky! My inner voice screams.
Corded 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 choose a pair of wide trousers from Clare Waight Keller’s Uniqlo:C colab (the butterscotch fabric is quite similar to Miu Miu’s corded trousers, which I admit I found in Selfridges the other day). Uniqlo: C pants are soft, fluffy and super easy to wear. The game-changing factor here is that they’re cut like flat-front trousers rather than jeans, which means I won’t be subjected to nightmarish teenage memories of myself turning into stiff, jumbo corded, straight legs.
Styling-wise, I had intended to pair the cords with a fair sweater vest (you’ve been spared that notion, dear reader; frankly, I looked like Tom) good life). Instead, the Telegraph team suggests a ruffled, embroidered, pin-cord blouse from Wyse that’s far more feminine and refreshing, and successfully resists 1970s geography teacher connotations. Another resounding victory.
Mini skirt
And so to the minis…. Despite my stubbornly entrenched ideas about appropriate skirt lengths
Pear-shaped bodies and minis have been on my mind since I re-read Mary Quant’s autobiography earlier this year; She was reminding myself how brave and sexy she was. I also met Rachel Peru, model, midlife influencer, and founder of the Liberté-Free to Be podcast, at a talk about Mary Quant at the Goodwood Revival. Rachel was sitting in the front row; She wore a form-fitting, above-the-knee Pucci dress and fondant pink tights: living proof that you don’t have to be curvy like Twiggy to look like a goddess in a mini dress.
Wool sweater, £245, Herd; Checked skirt, £219, sandro; Leather loafers, £375, Russell and Bromley; Gold-plated earrings, £290, Deborah Blyth
When Rachel and I emailed later, she told me that although she loved dressing up as a child, she lost confidence in her 20s and 30s and had to work to regain “healthier body acceptance.” She explains that she was actually afraid of shopping: “I could never find anything useful, I lost that sense of fun… Starting a new career as a model at the age of 46 also helped me, working with different stylists opened my mind to clothes I would never choose. I looked.”
I do my best to channel Rachel’s acceptance of her beautiful body as I look at the miniskirt options in the studio. I’m intrigued by a slightly punky Sandro skirt in a witty, menswear-appropriate tweed, but it looks really tiny on the gunwale. The Telegraph’s style director Tona explains that where the skirt sits will determine how short it looks on the leg, so I’ll never know until I try it on. Wise Words. It looks like the Sandro skirt is low and slouchy, with the hem falling just above my knee… and I love it. Instead of heels, I add a gorgeous pair of pearl-embellished loafers, which gives a nice cozy feel. Tona tells me to team this look with 40 denier pantyhose (I’ve been a 90 denier go-to for decades and am thoroughly bored with their matte dullness). This is another reminder of how energizing it can be to let someone shake up your ideas.
Overalls
Fourth challenge: overalls. In the interest of transparency, I should admit that I’ve worn overalls to a music festival before (though I’m not sure that really matters since pretty much everyone else that day seemed to be wearing bra tops and mermaid tails). What I want to know is if I can take off the jumpsuit for the office or for an evening out without looking like I’m dressed for a Challenge Anneka costume party.
One woman who knows this is Sarah Clark, stylist and founder of Douceur, who collaborated with By Iris on her own line of jumpsuits. “A jumpsuit and heels (especially a high metallic sandal) are always my go-to for evenings, and they’ve never failed me so far,” Sarah said. “The key to making a onesie work is undoubtedly proportions, which will vary greatly from person to person depending on body type/shape, height and preference. Although boring, if you’re a onesie virgin I’d recommend trying a few (ideally as many as possible) and in a variety of sizes if you’re looking for The One.
ba&sh Denim overalls, £300, Matches Fashion; Mary Jane shoes, £160, esska; Pearl and gold gezil earrings, £120, Deborah Blyth
After reviewing the options with the help of the Telegraph team, I settled on the ba&sh denim option, which somehow combines the sex appeal of Farrah Fawcett with the ready-for-anything vibe of Rosie the Riveter. Adding a Mary Jane with metallic high heels injects exactly that no-nonsense oomph I love when wearing a utilitarian staple. From table to cocktail? I’m ready for you.
All in all, I feel like I’m enjoying all the outfits I’ve put together (with the help of my friends) for my never-to-be-made challenge. To think about whether these pieces, which I have avoided for most of my adult life but now long for, have a common element: I guess there is freedom of movement, a feeling of comfort in my body. and adopting a lighter, less formal mood. I think about something Rachel told me about freeing her mind and starting to truly enjoy experimenting with fashion in her 40s: “I started focusing on how clothes made me.” to feelInstead of worrying about the so-called ‘rules’ that older women are often told.”
Hear, hear! After all, who wants to be stuck in Midis forever? Bring on the middle age minis!