I was already well into my fifties when I became, very suddenly, obsessed with fashion. All of it: style, brands, how I dress — and noticing how other people look, and the details and trends on the street. It’s become one of the great joys of my life. When I told a colleague on the FT’s Style desk about this conversion, she was surprised. “It’s more usual to have always been interested in fashion,” she said.
I was not born with a sense of style, nor did I develop one. Indeed, in my twenties I wore the drab uniform of my tribe: bookish young women who thought fashion “shallow” and were destined for publishing, academia or journalism (where we would anyway never be paid enough to dress smartly). I didn’t wear high heels for work, so I never learnt to walk in them — which I regret. Relatedly, I rejected clothing that might call attention to the fact that I had a body. I regret that, too.
Looking at photos of myself at 40ish, I see a woman in crisis, starting with the clothes. While my children are smart and smiling in Mini Boden, I wear items (“pieces” is too strong a word here) that are shapeless, boring — or desperately zany: candy-coloured horizontal stripes, tight across an ample chest. I loved Trinny Woodall and Susannah Constantine’s brutal 2000s makeover show What Not To Wear, where the pair forced baggily dressed women out of beige cargo pants and into fitted V-neck sweaters. Yet I never learnt any of the lessons.
I meandered onwards, working too hard at juggling my family and career to think about clothes. I was never the worst-dressed woman in the room, at least. That was enough. Until it wasn’t.
The first thing that happened was that my apparently stable marriage turned out to be nothing of the sort. It was devastating, but amid the fallout, one thing I could control was how I presented myself. At around the same time, I’d moved from editing to a “public-facing” role, including hosting an FT podcast, newsletter and chairing events. I would never have perfectly coiffed hair, nor did I want to wear colour-blocked “professional attire” on stage, like many women in the corporate speaking world. But I did need to build a brand, an image, for myself. And I really wanted new clothes.
I started off by scrolling clothing websites to get an idea of how to put outfits together. I did it first thing in the morning, a caffeine shot to a dormant system. Instagram smelled the change and started to taunt me with older fashion influencers showcasing outfits and under-the-radar brands. They looked like they were owning life. And I wanted a piece of it. Or, rather, many pieces of it.
It started with a coat. A bright blue coat with contrast red ric-rac trim, designed in 2022 for John Lewis by the stylist Erica Davies. People complimented me every time I wore it. After a lifetime of grey, black and navy coats, I had popped some colour.
That coat kick-started an ongoing programme of learning a new visual language. I scooped up bargains from Margaret Howell and Studio Nicholson, and raced to get ahold of collabs such as M&S x Bella Freud. As a “jeans and a jacket” person, a favourite discovery is Paynter, a London-based brand that offers a small run of jackets a few times a year. It’s a race to sign up before they sell out. I’ve got lucky: two light Paynter jackets (chore and cord), plus a heavier wool one, and there’s a summer coat on order. My love of the “small batch jacket” has become a family joke.
I picked up Marks and Spencer’s horseshoe jeans, a shape I would previously have dismissed as weird and attention-seeking, but which turns out to be extremely flattering. Now these £40 jeans have become a slightly cultish phenomenon (“famous”, says Grazia magazine). Along the way I made a big investment in a bespoke suit, as a kind of armour for the public-facing parts of my job.
How would I describe my dress sense now? Sensible, with a dash of frivolity. I have to project credibility when I talk publicly about the stuff I am expert in — workplaces, leadership and the future of work — and my professional clothes reflect that. But by accepting my unruly curls, rather than straightening them in a more “corporate” way, it signals, I hope, that I don’t take myself too seriously. And I’ll add a bit of colour, and usually a pair of trainers (I’m into new New Balance and retro Autry at the moment). There’s also a lot more jewellery than I ever wore previously (also: more piercings and tattoos). I am not going gently into post-meno invisibility; sod that.
Futurist and brand strategist Lucie Greene places my obsession within the wider reframing of what style looks like for older women: a letting go of what was once considered appropriate. “It’s linked to the fact they are still in the workforce and still earning a lot of money,” she says. Another shift is that a lot of us are now often seen on Instagram, LinkedIn and even TikTok.
Most profound, Greene says, is that “women are dressing for themselves, at all ages. It was about the male gaze in the ’90s, I think, and then it was about conveying power — the power suit for women — and now I think it’s about curating personal taste and brand, and dressing for yourself.”
Successful women are no longer tied to visibly high-status, designer brands, either. “I still see plenty of Chanel suits on the conference circuit,” Greene says, “but their prices went so crazy and it’s created a window for these wearable, inclusive, cut-driven and chic labels like Aligne. And they’re affordable as well.”
I follow a lot of these newer brands on Instagram, but my tastes have mainly been shaped by individuals: Davies and other fashion Instagrammers such as Kat Farmer, and also by writers.
My favourite guru, though, is Kate Hiscox, who writes the Wearsmymoney fashion blog. I came to Hiscox early, drawn by her witty, down-to-earth writing (she used to be in the music business) and the way she puts outfits together. This season, for example, her “best suede on the high street” post inspired me to dig out Grenson moccasins from the back of the cupboard.
Hiscox’s readers range from their mid-thirties to their seventies. On a video call in front of a whole wall unit filled with trainers, she tells me that she gets many emails from women who had lost interest in fashion before finding her blog. “They were wearing the same leggings, the same sweatshirt, every day and just feeling bad about themselves.”
What, I asked her, is the key to dressing well in your fifties and beyond? “It’s about having the best basics. So I would always say, get the best-fitting pair of jeans and spend money on things: so if you always wear a blazer, get one really good blazer, not three mediocre ones.
“So have best plain white T-shirt, the best grey cashmere jumper, the best pair of boots. And then you can add accessories and trendy pieces that don’t have to be expensive, because you’re not going to wear that leopard-print scarf for the next 20 years, but you might wear it for the next two years.”
And with that, I am down another style rabbit hole. The perfect white T-shirt is my next quest. Suggestions welcome.
Isabel Berwick is FT Working It editor and author of ‘The Future-Proof Career’
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