“People think of chic as something that’s quite serious, but it’s not true,” said American designer Michael Kors. What is true is that women, especially in midlife and beyond, often dress with more gravity than whimsy; the wit and levity of their personalities frequently no longer reflected in their wardrobes.

Perhaps it’s not surprising when you look at and listen to, fashion industry heavy-hitters such as the stalactite-like Anna Wintour, whose wardrobe is as sobering as her infrequently-seen smile, or former UK Vogue editor Alexandra Schulman, who has denounced wearing frills over 40 and damned 50-year-old model Helena Christensen for wearing a lace bustier (over jeans) to a party, claiming she was too old to wear it. Is it any wonder that many women find fashion fearsome rather than fun? Is it any surprise that some would rather play it safe than play with their look?

I often think clothes rather than eyes are a window to the soul. In midlife, our outfits can begin to look as serious as our schedules and as joyless as a Saturday night with screaming toddlers. Fashion falls to the bottom of our priority list as we navigate the obstacles of midlife, from raising children to managing menopause, from relationship breakdowns to career pivots. The La La Land yellows and ruby slippers we wore to have fun in our twenties feel too frivolous and fluffy now. Cruelly, most of us could have worn a black sack in our twenties and still looked fresh and fun because our bodies were lithe and our faces lit up with excitement and optimism.

Dressing as we age can be a sartorial minefield because nobody wants to wind up wearing beige flannel separates either.

I’ve always believed that the key to dressing well at any age is to dress for your personality; aligning your attire with your attitude you might say.

But even for those of you (like me) who are about as bubbly as a pint of beer left sitting in the sun, there remains a place for whimsy in your wardrobe. Not only can wit and whimsy bring an agelessness to your appearance that will be kinder and more convincing than a nip and tuck - and much less expensive - but a fun flourish added to an outfit will put a smile on your face (whether you’re feeling it or not) and on others’.

I started to radically rethink how women should dress in midlife and beyond when I came across little-known French designer Fanny Karst, founder of the fashion label Old Ladies Rebellion, several years ago. Although she designs specifically for women over 60, her pieces would sit comfortably in the wardrobes of women 20 and 30 years younger; I’d happily buy one of her shift dresses if I could afford it. The key elements of her designs are bold digital prints, trompe-l’oeil and ironic statements including “Not At Your Age” and “Old Is Gold” - hardly the anchors of traditional designs for women of a certain age. Created in sophisticated washed silks and in a palette of french greys and blues, there’s nothing wishy-washy about these clothes.

I had never before seen older women dressed this way. I’d seen them either looking bland and beige or sophisticated and classic, but not modern and edgy. Karst’s pieces are fresh and contemporary, in part, because they are unexpected. Slogan sweatshirts have always been the uniform of energetic teens and enthusiastic collegiates, not grandmothers and grey-haired octogenarians. But Karst’s designs don't patronise her clients, instead, they’re about sharing a joke. She describes the humour in her designs as “a common wink, an intergenerational understanding. It reflects what we have in common and my admiration [of these women].” The 35-year-old (Surprised? So was I) avoids caricature by keeping her cuts streamlined and unfussy. The facetiousness in her collections never descends into clownishness. She gives her clients not just a look but an attitude, which is sexy, youthful, attractive and fun.

One of the most refreshing quotes I’ve read recently about fashion is from actress Zoe Kravitz. “Humour is a big part of my style. You have to be willing to fall on your face a bit, to be that fashion roadkill,” she said. We become so risk-averse in mid-life, protecting who and what we love, that we forget fashion is there to have fun with. As designer Carolina Herrera said, “What is fashion if not change, newness and experiment? It keeps you youthful.“ And what’s the worst that can happen? You get noticed, probably.

Like anything in life, you can’t please all of the people all of the time, but you can please yourself. The days of fearfully following mythic fashion rules have fallen by the wayside anyway. In 2020, individuality is everything.

Even British Vogue last year “congratulated” actress and director Greta Gerwig on being the red carpet’s queen of whimsy, while Saoirse Ronan’s stylist Elizabeth Saltzman told Vogue.com that the looks she chooses for the Irish actress are about the “joy and the folly” that fashion should provide. Admittedly, folly is easier to pull off in your twenties, but midlife has one very important advantage over youth - you stop caring so much what other people think. The self-consciousness and reserve of our early years slowly disappear.

Colour is where I get playful with my wardrobe. Mixing unexpected shades brings me joy and adds modernity and individuality to the clean lines and simple shapes I favour. Tropical Popical owner Andrea Horan knows how to liven up any look with bold accessories and is a true proponent of Louis Vuitton creative director Nicolas Ghesquiére’s description of fashion as “a playground”. PR guru Tara O’Connor loves a turban, Irish artist Alice Maher a quirky print, while Tracee Ellis Ross could make summer sequins look appropriate for a funeral. Watching the joy she gets from her wardrobe and her beauty looks (those lip shades!) brings me so much joy. If anyone understands carefree dressing with whimsy in middle age, Tracee does.

Former First Lady Michelle Obama, meanwhile, masterfully managed to have fun with her wardrobe despite being in a position of serious power. Those pretty prints, bold colours and hints of sparkle injected fun and energy into her wardrobe, showcasing her personality and attitude to life unlike her successor Melania Trump, who always plays it straight and when she tries to be more casual she gets it horribly wrong with a Zara jacket and an inappropriate logo.

When Victoria Beckham was pictured in her Fashion Stole My Smile T-Shirt a couple of years ago, she made everybody else smile along with her. The trick to feeling good in our clothes as we get older is to forget about any cookie-cutter ideas on how to dress as we age and dress exactly as we want to.

Marie Kelly, June 2020.