Why we definitely get more stylish as we get older
Photo: Claire Pepper
After years of trying various trends and faffing around with ill-fitting clothes, I’ve finally found my style groove. At 57, I know what I like and how I want to look. Gone are the days when, as a magazine fashion editor, I thought I had to keep up with what was in fashion – I can remember a cheap leather pencil skirt that would spin around my thighs like a hoola hoop every time I walked from one end of the office to the other. And swapping comfy trainers for the toe-squeezing shoes kept under my desk. Now I wear what I like and hang onto my money. More attention is paid to quality and fit ( I no longer buy trousers that are just that little bit too short in the rise and put up with the crotch-bothering inconvenience) and flash-in-the-pan fashion fads are shunned in favour of feel-good clothes.
While experience and gut instinct have a part to play when putting outfits together, or buying something new, it pays to Know Your Style – to be able to sum up your signature look. Treat it as a ‘Wardrobe Pitch’. Imagine if someone asked you to describe your style and how you like to dress (in a couple of sentences). What would you say? As a journalist and author, I’ve been been asked this question numerous times and so can reel off something about Gentlewoman Style, jeans, jumpsuits and sharp jackets. I can list my style icons from Katharine Hepburn to Tilda Swinton (how good does she look at Cannes?). Plus, the labels and brands that work for me.
But I do believe that style is a work in progress, that we continue to grow and change. Which is a wonderful thing. Over the last few years, I’ve definitely become a Skirt Convert. Could be because our summers in the UK are getting warmer, or maybe it’s a bit of Devil May Care attitude kicking in. Regularly posting on That’s Not My Age and writing my column for the Telegraph has forced me to try new silhouettes and shapes and not just stick with my trademark utilitarian look. Statement skirts and chunky sandals, who’d have thought it? In my 50s, I’m open to giving clothes I’ve never considered before, a go, making an effort to be more creative with my outfits and honestly enjoying it. Of course, flat shoes and sneakers are a non-negotiable. Comfort is everything.
The menopause has not been easy ( HRT has helped), but I am much more ‘ no nonsense’ both in terms of personality and when it comes to what to wear. Faff-free all round. I know how to say ‘no’, in a polite way, I feel happier in my own skin and more confident than my younger self. It helps that my Instagram feed is full of gorgeous women over-50, such as, Kemi Telford, Linda V Wright and Jannine Newman (who sells vintage clothes at Under the Cloth); style queens who are more than just the clothes they wear. In addition, meeting numerous Creative Women for my regular series continues to be both an adventure and an education. Proof that style and substance can and do co-exist – which is also abundantly clear when I read your comments on That’s Not My Age.
I’m reminded of my interview with Lucinda Chambers, who told me that, ‘The most stylish women I know are older…one is in her eighties and the other her sixties. I think it takes time and that’s all right.’
We’re all styling it out, experimenting with our signature look and wearing what we please. Self-acceptance and feeling comfortable in our own skin (even if it is a bit wrinkly) come with the midlife territory. I’m not boasting when I say that my sixth decade has been my most stylish yet.
More statement skirts and chunky sandals, here:
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STYLE NOTES: The navy cotton shirt is an old Eileen Fisher. Stitched Masa Shibori cotton skirt was a very generous gift from Toast (it’s a beauty and almost sold out). My silver rings are from Claire Stratton. The wooden bangle is from Branch Jewellery. Chunky sandals were gifted by Grenson. The canvas bag in the second photo loaned from sustainable brand LPOL and returned.
Discussion (33 Comments)
Nicola says:
Whilst I completely agree with you Alyson I also think this is highly subjective! I often think if my 18 year old self could see me now she would be both pleased and appalled. Pleased that I am so comfortable in my skin and clothes and appalled by those same clothes. Although having said that a friend recently put up a photo of a group of us in the 6th form ( in 1981 I think – Princess Diana had just become a big influence) and there I was in a cashmere sweater and pearls. Have a guess what I’m wearing as I type this?
I think that we learn with age what suits us, and what lengths we are prepared to go to to look ( in our view) stylish. Here at TNMA we are a tribe and I think a lot of us agree on what that is – and are supportive of one another. However, I do have to move in groups where women are not so supportive of one another, who do look down on the woman who decides not to wear spanx, figure hugging and revealing clothing and does not have Botox. And one of the most stylish people I’ve ever known has been reduced to tears because her daughter was bullied because of her mother’s clothes.
Keep up the good work Alyson – we need more people like you reminding the world that getting older and daring to follow your own style is worthy.
Thanks Nicola, agree with you about the lovely community we have here. I’m with Madeleine Albright on the subject of women not supporting other women…
And I’m sorry to hear about your friend’s experience. People can be so mean. One of my old college friends has a very stylish mother and the same thing happened to her at school – though that was approx 45 years ago, you think we’ve moved on and then….. I hope your friend reported the bullying to the headteacher.
Lynn says:
Nicola — your friends daughter’s experience speaks to one of my worries. I’m a style confident, older mom of a primary school daughter. We live in a city where most women conform to a single look. But we will cross that bridge when we come to it!
bev says:
You look very fab and contented in the photos! I agree, I am only just getting the hang of it at 63 – having experimented (often comically) and also tried to fit in (especially the 80s with all that nonsense power-dressing malarkey) I know what suits me and what feels comfortable. Sometimes a little hard not too fall too firmly into the comfort dressing (bit scruffy?) zone but minimal effort with ye olde word ‘grooming’ (I sound like Katie Boyle) with decent haircut, minimal makeup and handcare seems to work for me. I would be LOST without my accessories (scarves, footwear and quality bags) and costume jewellery which tend to speak for me more than the clothing now.
Sara says:
That really made me smile! How many of us see ourselves in your lovely funny comments, Bev. I’m certainly in there somewhere, hoping to reach Alyson’s style assurance. Better now than earlier in my life, by which I think there are fewer mistakes and more happy choices.
Alison Simpson says:
My 28 year old son describes my look as ‘space pirate’. I am happy to embrace it. It involves a mixture of graphic, close to the body clothes with big billowing coats thrown over the top, and in winter as many layers as I can get on and still have a shape! Add a bunch of heavy silver chains (he’s a jeweller) and we’re done. As you can imagine, I struggle with summer, but we live in the north of Scotland. Yes! I’’m all for owning your style. I know it probably sounds dreadful, but he’s pretty critical and wouldn’t let me leave the house if it didn’t work!
Kellie says:
I really needed this. I’m 57, and struggling with a changing metabolism and shape. I agree with you, and feel I’m finally in a place where I know my own personal style, and what works for me. I’ve also let go of several pencil skirts! Stylish clothes make me feel good, as long as they’re right for me, my shape, etc. One of my biggest fears is looking frumpy (the “F word”, as I call it), or wearing anything that veers into old lady territory. I find that adding something edgy to an outfit helps combat that. As I get older, I’m more comfortable taking risks, as long as they keep the overall look classy!
Ellen says:
To me, “frumpy” is more a result of bad fit or fabric that drapes in unfortunate ways. Playing around with different sizes can offer up some pleasant surprises. As my shape has relentlessly morphed into an apple, I am finding more substantial fabrics look better, and that it is worth the effort finding those clothing lines that fit one’s body. Some.Just.Don’t. And/or have a good tailor on call!
Lynne Collins says:
I know it’s a well worn saying but style isn’t necessarily about fashion. I have a mixture of age-neutral High Street and vintage (my favourite being a tailored black leather coat bought for £10 in a charity shop). For me, hurtling towards 68, it’s been about accepting change and working with it. For the past 50 years my hair has been coloured blonde and during last year’s lockdown I found my real hair colour is now a rather splendid platinum. Bring it on!
I have a friend who had the same hair experience and her new platinum gray is fabulous. I actually have been excited to be getting enough fray in my hair for it to be noticeable!
Oh my gosh you look AMAZING!!! I have watched your style evolve for over a decade and you just get better every year.
I agree totally. Looking back at a Daily Mail article from 2015 Alyson has been put in a knee length shift dress and court shoes – TRAGIC!!! I know that Alyson would never have chosen that herself and expression tells it all!
Louise says:
What I am most enjoying at this age (58), is knowing that the clothes I have now, I hope to still have for decades to come, so all the enjoyment I have wearing them now will be a continuing pleasure. I am enjoying identifying my style (if not categorizing it – I can’t sum it up, but I know that it is all about a plethora of patterns and lovely fabrics in clothes with straightforward cuts), and I’m also enjoying letting go of feeling slightly apologetic about loving clothes and being good at putting them together.
Susanna says:
Louise, that’s so helpful! I struggle to define my style, but I do know it’s all about fabrics (more substantial these days), patterns, textures, and “straightforward cuts” – love that phrase. As I approach 65 I find that I “know it when I see it” much more often than I used to, and I’m willing to make the investment for fewer clothes that I will wear for years to come. I am becoming a little more reconciled with the inexorably thickening middle, having been an hour glass all my life, but I still haven’t decided about the fate of the pencil skirts! Alyson, thank you for your posts that really capture the inner shifts that we have to make as we grow into ourselves in mid-life and beyond.
Yvonne says:
You look fabulous in that beautiful top and gorgeous skirt. Love your post about women finding their style and being themselves. I am getting there and care a lot less about what others people think of me. So freeing after years of people-pleasing. A few days ago I bought myself a beautiful hand-made silver necklace with the number 1 for a pendant. Subtle and reminds me to treat myself first as I have always treated myself last for years . I am proud of who I am. It has been a long road and it’s not over. Women need to support each other. Thank you for your beautiful blog! So freeing!!!
You discovered the wonderful truth—that older really is more stylish as we truly come into ourselves—sooner than I did. Lucky you! But it’s true. At 79 I will no longer, never-ever wear anything I don’t love and don’t feel comfortable in. That includes man-tailored shirts, trench coats and a host of other wardrobe “staples” that are just not my style. On the other hand, this I-hate-jeans person finally found the first pair she didn’t hate, and now I love wearing jeans! As we go forward there should be no closed doors, including the closet.
I am turning 60 this year, which seems to have sparked a lot of internal debate about what I want to have in my closet going forward. I still love my vintage pieces from the 80’s (the bold shapes and colours suit me) but pieces from earlier decades no longer fit my ageing shape. I still try to buy as much as possible second hand, but I will splurge on contemporary pieces that are of good quality (as you noted, more substantial fabric is much appreciated now). I will always love a “dramatic and weird” piece (words from the lovely ladies in my local thrift store) but I also want to have more pieces that will look as good on me 10 years in the future as they do now. I love your outfit in this post, especially the chunky sandals.
carole b says:
I’m 63 now, and agree with others that I know immediately what suits me and what doesn’t. I’m mostly drawn to vintage – just the quality of materials and design… bought a wonderful dress last week in Ludlow – 70’s patterned cotton shift dress (but shaped, with darts), just below knee length, handmade in Bangkok. Like another contributor I used to be ‘hour-glass’ but am noticing the inexorable changes to body shape. So in addition to my own yoga practice and brisk walking I’ve recently started weight lifting/training with a PT – I’m aiming to build bone density as well as toning up… It’s interesting!
Mrs Tonia says:
Another flattering and well put together outfit on you in the photo Alyson.
Your overall advice both in your second book and these columns have guided me towards finding my more mature style. But thankfully it’s not that different from what I’ve always liked to wear. Same colours and patterns as ever like gingham and woven checks. A perennial in my wardrobe but my tolerance of too tight and uncomfortable clothing has diminished. I don’t want to put on and wear anything too tight or constructive. So looser silhouettes now without being too baggy. Nothing too waisted. Longer skirts I like and comfortable footwear.
The Birkenstock’s and similar have made my fashionable shoes near on intolerable. Yesterday on a very warm day to have drinks with friends outdoors, finally okay to meet, I put on a chartreuse semi fitted linen dress with cap sleeves and an asymmetrical hemline well to mid calf length. Perfect with strappy block heeled silver leather sandals I had made to order in Florida. Years old both items but looking and feeling good still. My style is consistent. Shape hasn’t changed too much due to adequate exercise but now with silvery longer hairstyle and lots of silver bracelets and rings. Good to go.Anita says:
Totally agree Alison, at 56, I know instantly just by look if a style will suit me.. I also don’t waste time with anything that ‘flaffs’ – ties on shoulder, off shoulder or frills and lacy bits that need to sit just so… from a jeans girl I’m now a dresses girl and loving print mix and jewellery combinations..
Bron says:
Well said! At 61, I feel more confident with my fashion these days than I ever have. Like most people, I look back on pics from the 80s and think – what the heck was I thinking with that outfit?! I am, as you have said in one of your posts, a work in progress. I have decided to heck with it if people think I have mutton dressed like lamb overtones with some of my outfits. Here in Australia I have found a brand that has some ‘out there’ patterns which I have now embraced. It empowers me to continue wearing them when I get Many comments on said outfits. Embracing my inner quirkiness!
Rach with an E says:
Couldn’t have said it better myself, Alyson! My 18 yo calls me style ScandiJapanese which I’m happy with. Having recently got a new job, I am confident turning up in flat shoes or stylish trainers which seem to be more acceptable at work post pandemic. It also means I can cycle or walk home comfortably, rather than drive.
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This is so true. And love that skirt