How to look great in jeans at every age

Telegraph

29-05-2025

Trends may come and trends may go, but one thing remains true: A reliable pair of jeans or (or two) is the foundation of every well-dressed woman's wardrobe – whatever your age. The etiquette of where and when you can wear jeans has changed radically, of course. Now it's perfectly acceptable to wear a smart dark wash denim jean to work or on a night out.
However, the key to looking and feeling confident in jeans is fit. And here's the rub… confusing sizing and the frustrations of navigating websites mean that we've fallen out of love with shopping. That's why so many of us stick to whatever jeans we've worn for the last 10 years (or whatever is in the cupboard); so we never really get on board with flattering modern new cuts like barrel-leg jeans, or cropped styles that work really well in summer.
'Jeans are so many women's nemesis when it comes to the try-on process but they are the one item that can elevate casual looks and also refresh an outfit so it looks contemporary,' says Alexandra Fullerton, who is not only a regular Telegraph contributor, but a personal stylist, who regularly helps clients get over their jeans-trying phobias. 'The process has to be kind and needs to be considerate to any past traumas in the changing room… My role is to honestly advise on how things look (I take videos to show clients the 360 view of what flatters – or not) and also share my thoughts on what trends have longevity and making sure the client invests in denim in the best way for their lifestyle.'
Happily the British high street is still a good hunting ground for jeans. In fact, M&S denim has several devotees in the Telegraph offices (the stores's 2024/25 results showed they sold more than 10 million pairs of jeans – there's been a 7 per cent rise compared with last year – and prior to their recent cyber-hack troubles they were selling ten pairs of jeans every minute). While my stylish colleague Lisa Markwell favours 'Tesco's dark denim wide-leg jeans' and the subtle details – raw hems, patch pockets – that the store's design team introduce to update their core fits.
'Getting back in the game is the best way of reigniting your understanding of shopping – particularly for jeans,' counsels Fullerton. 'Plan a morning and head to a multi-brand boutique or department store and be prepared with coffee and an open mind. Take a stylish friend, or a stylist, for non-biased opinions and be prepared to spend time reacquainting yourself with all the new cuts and silhouettes. Size up to begin with, there is nothing worse – or more dated looking – than squeezing into something too tight. Take lots of pictures, from all angles too (this is where a friend comes in handy) as well as for moral support.'
With this advice in mind, the Telegraph team scoured the stores to showcase jeans that work well for our different ages and personal styles, putting together two different looks: one casual and one smart. Get thee to a changing room – and find your true blue hero fits!
Skip to:
20s
30s
40s
50s
60s
Sophie Tobin – 20s
Casual
Agolde Kelly high rise straight leg jeans, £300, Net-a-Porter net-a-porter.com; Sacai Nylon bomber jacket, £680, MyTheresa; Shirt, from a selection, Cos; Hai Silk shoes, £142, Whistles; Gold plated earrings, £359, Tom Wood
I'm 6ft so good quality jeans at the right length are few and far between. I've tried a crop (on me they're more like pedal pushers), dipped into the Mom jean trend (the narrowed ankle makes everything very top heavy) and given a loose wide leg a go (way too much fabric swishing around) and have come to the conclusion that there is nothing better than the classic straight leg.
I have three pairs of jeans in my rotation and prefer a thicker denim which means they keep their shape, last for years and justify a higher price point. So many high-street stores don't offer longer lengths (Topshop Tall used to be my go to) but I've found Abercrombie & Fitch, M&S and Zara are your best bet if you don't mind stretch denim.
Smart
Ayla polish denim trousers, £340, Citizens of Humanity; Tubular knitted tank, £45, Cos; Leather belt, £125, J&M Davidson; Loafers, from a selection, Russell & Bromley; White rhodium plated earrings, £299, Tom Wood
I always make sure to try on jeans with the highest shoes I would wear them with to get the length perfect and when shopping online, I check the height of the model. Another trick is to buy turn up hem jeans and turn them down (if you're getting them tailored remember that you can take fabric away but you can't add it on).
For smarter denim, I've chosen these subtle tapered-leg jeans which are just different enough from my day-to-day straight legs and are cut to a trouser fit, making them feel a little more special. Made from Eco-Indigo, these jeans are guaranteed to last a lifetime and at the perfect length the cost-per-wear will be worth it.
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Sonia Haria – 30s
Casual
High waisted cropped flare jeans, £39.50, Marks & Spencer; Blouse, from a selection, Sezane; Leather tote bag, £155, & Other Stories; Shoes Sonia's own
My weekend uniform usually consists of a dark grey or mid-blue pair of straight-leg jeans with a T-shirt or cotton shirt. This takes me from early morning kids football practice to an afternoon barbeque with friends (I just swap out my trainers for a pair of sandals). I am in jeans most of the time and have more pairs in my wardrobe than I care to admit – except I didn't have a pale blue pair like the ones by M&S worn in our shoot. I'm really taken with them; I've paired the jeans with one of my favourite jazzy floral shirts by Sezane and the leopard-printed leather sandals by Topshop I have worn for the past seven summers. I also love the kick-flared cropped length of the jeans; at 5ft 3in, I avoid very baggy shapes, and I found this cut to be surprisingly flattering. A bargain for under £40, too.
Smart
High waisted denim trousers, £125, Sezane; Top, from a selection, Cos; Shoes, from a selection, Marks & Spencer
For the evening, high-waisted, dark-washed denim in a wide-leg shape is very much my comfort zone. This pair of jeans by Sezane are utter perfection. They are too long to wear with flat shoes, but I'm not mad about that – if I'm out for a dinner with friends, I will usually be in some sort of comfortable heeled sandal anyway. I think this is a classic pair of jeans that will never date, and although they are wider in structure, I've paired them with a fitted linen bandeau top by Cos for some balance. The whole outfit is just dressy enough for my liking, and the bare neckline means I can wear some sort of fun necklace (in this case, a 4 euro beaded choker from a Greek market a few weeks ago).
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Tamara Abraham – 40s
Casual
Extreme tapered jean, £175, Me+Em; Organic cotton T-shirt, £30, Colourful Standard
I've developed an addiction to barrel-leg jeans, the more exaggerated the better. Some friends are baffled by this, convinced they're a shortcut to broader hips, but I find them to be flattering, nipping in my waist, yet delivering a slightly grunge-y slouch that's pleasing to the Nineties teenager in me. The shape makes all my staple shirts, T-shirts and blazers look more current – anything that helps my existing wardrobe work harder is a win for me.
My all-time favourites are the Sienna Miller for M&S grey cropped barrel-leg jeans – you can't buy them new anymore, but I've just tracked down a white pair on Vinted for £30. For blue denim the wash of this Me+Em pair is spot on. As a general rule, non-stretch denim is key – it requires a little wearing-in but the way it hangs on the body is so much more effortless and expensive-looking.
Smart
The Kite Rancher argyle frayed jacquard denim jeans, £325, Wiggy Kit; Silk top, £150, Rise & Fall; Suede shoes, £450, Toteme; Rope-chian necklace, £44.99, H&M
This silhouette transcends into eveningwear beautifully, and white jeans look so elegant when you add heels and jewellery. This Wiggy Kit pair has a frayed argyle pattern woven into the denim that makes it more formal. There are also buttons at the back to adjust the fit at the waist. I'm 5ft 4in, so somewhere between petite and regular – those shorter of stature will love Mother's cream Lil' Mother Half-Pipe ankle jeans with black piping down the leg.
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Sarah Bailey – 50s
Casual
XL Straight jeans, £110, Levi's; Reversible denim and nylon blouson, £860, Levi's x Sacai; Tencel lyocell shirt, £130, With Nothing Underneath; Suede shoes, £150, Esska
I love the sassy, can-do energy that wearing a great pair of jeans can bestow. But, of course, if you are wearing a style that is too tight and cuts you in half when you sit down… well, all that goes out the window.
I blame my 1980s and 1990s youth, but for years I associated looking fashionable in jeans with sausaging my legs into the most uncomfortable straight-leg/drain-pipe/spray-on styles imaginable. The thigh chafing wore me down after a while, and I confess, I went through a few no jeans years. But now, in my 50s, I am a jeans wearer once more and I give rousing thanks for the advent of wide-legs, barrel-legs and boyfriend styles. In fact, I feel I can bravely assert that you can no longer say that there isn't a style of jean that suits you, you simply haven't tried on enough pairs yet!
Smart
Stella A-line jeans, £85, Lee; Silk blouse, £375, Philippa London; Leather shoes, £199, Penelope Chilvers
For our shoot, I revisited two of the classic American denim brands – Levi's and Lee. These Levi's XL Straight Jeans are soft and slouchy (and come with a cute tie belt if that is your thing). I've been road-testing the pair you see here at weekends with trainers and a bomber jacket and I love them (let's say, they have 'anti-aged' my wardrobe).
The Lee 'Stella' jeans I'm wearing in the picture for my 'smart' look have a tighter waist and a sharper leg, but I'm delighted to report there is no compromise in terms of comfort. I really enjoyed styling them with this puff-sleeved fondant pink blouse by Philippa London. On my frame at least (I'm 5ft 4in), this style looks best with a heel and with these gorgeous Penelope Chilvers numbers on my toes, I really feel like I could go anywhere.
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Lisa Armstrong – 60s
Casual
Taylor relaxed barrel leg jeans, £301, DL1961; Tencel lyocell shirt, £120, With Nothing Underneath; Shoes: Lisa's own; Earrings: Dinosaur
I weeded out all the old jeans I no longer wear a while back and am now at half a dozen pairs, including some dark straight-leg Acne's I bought 12 years ago and still love. My other perennials are a pair of straight-leg Levi's (mid wash) and some slightly darker Khaite Abigail straight legs from Net-A-Porter. They're always sold out but this size must have been returned. Lesson: always turn on your notifications and get your name on a waiting list. Both work, on Net-A-Porter at least.
Having got to an edit I wear all the time, including weekends in the country, where wide legs just aren't compatible with wellies, I very rarely buy new jeans. I love the up to date look of these looser cuts though, particularly the Gap ones, which feel ultra soft and floppy. I like to keep a note of current trends, but I'm never doing low rise again. They're so unflattering – and chilly. Bell bottoms are also off the list.
I wouldn't normally go as faded as the DL1961s. Nothing to do with my age, but for me, faded equals a casual look, whereas something darker is more versatile. Come to think of it, maybe that notion is to do with my age.
Smart
Wide leg jeans, £50, Gap; Tweed jacket, £589, Ridley London; Supima cotton T-shirt, £14.90, Uniqlo; Reversible leather and suede belt, £95, Me+Em; Leather bag, £265, Stow London
These days, dressing something up isn't necessarily about adding heels or sparkle. It's more a question of wearing them with beautiful shirts or the perfect T-shirt. I also love the idea of them with a Dior Bar jacket (who doesn't? You can find these for much less on the pre-worn sites). Interesting flats and velvet mules can look sophisticated and modern with jeans. I love them with classic cropped boucle jackets too. At a certain age, you have to start mixing your classics with casual or more punk pieces, otherwise you can look very staid. This jacket's from Ridley London – choose from a range of tweeds and they'll make you one in 10 days.
I love the fact that DL 1961 uses a tenth the amount of water of the average jean manufacturer to make each pair. E.L.V. Denim is another great sustainable brand which upcycled old jeans into innovative new styles.
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