The 25 best-dressed women of 2021, aged 29 to 100

1. Princess Caroline of Monaco

While the attention of the world’s press might have been on her sister-in-law, Princess Charlene and her dramatic disappearance/ return/ disappearance, Monaco’s Princess Caroline has serenely and elegantly been getting on with the job of looking effortlessly chic for the increased number of duties she’s taken on. She mostly wears Chanel, but this Halston jumpsuit was a low-key yet sophisticated highlight (if you’re working out how to dress for newly-grey hair, let her be your muse, too). Bethan Holt

2. Joan Collins

Joan Collins turned 88 this year and is looking as twinkly and glam as ever, putting women a quarter of her age to shame with outfits which always hint that this is the actress who played Alexis Colby. Whether she’s in tailoring, evening gowns or a wafty kaftan in St Tropez, Collins’ standards never slip – and she’s always dripping in jewels. BH

3. Sarah Jessica Parker

Whatever you think of Carrie’s outfits in And Just Like That..., SJP has a rare sense of style that can carry anything off. This is high-wire dressing that most of us don’t need to try out. But if it was great watching her wear Vivienne Westwood’s more outré looks in her 30s, now that she’s 55 it’s inspiring. Lisa Armstrong

4. Gabby Logan

After Team GB’s Olympic success, it might seem trite to cite Gabby Logan’s style as a standout moment from the Games – but it was if you have a keen interest in these things, as we do on these pages. From Me + Em dresses to Roland Mouret tailoring, Logan and her stylist Charlotte Handley Green offer a masterclass in looking sharp and modern in midlife. BH

5. Iris Apfel

Iris Apfel’s maximalist style has nothing to do with trends and everything to do with pleasing herself. Those bold, round specs are her signature, while her neck and arms are always stacked with colourful jewellery. 2021 was a milestone for Apfel, who turned 100 in August, and to mark the occasion she announced that she was doing a collaboration with H&M – proof, surely, that ageism is finally falling out of fashion. Tamara Abraham

6. Maye Musk

Musk’s tagline is: “It’s great to be 73.” It’s a motto she personifies with her zest for life and experimental style. Working with stylist Julia Perry (they met when they were both working at a modelling school, struggling to make ends meet), Elon’s mother has delivered some inspired looks this year – including this slouchy peach Burberry suit. “I need to make sure I don’t look like a frumpy granny,” she told me recently – there’s no danger of that. BH

7. Sandra Oh

Is there any look Sandra Oh can’t carry off? From a gold lamé co-ord by The Vampire’s Wife to polka-dots and black-framed eyewear, the 50-year-old actress’s red carpet style game is consistently strong. So too are her on-screen looks; her latest role as a professor at a fictional Ivy League university in Netflix series The Chair is rich in grown-up style inspiration. Try buttoned-up blouses and just-collegiate-enough tweed jackets to get the look. TA

8. Yasmin Le Bon

At 57, Yasmin Le Bon’s still got that cool girl vibe about her that made her such a successful model in the Nineties – yet she’s also an everywoman who is happy to rummage for gems in a thrift shop like the rest of us. She wears a mish-mash of vintage and designer pieces from Gucci and Isabel Marant, anchored by androgynous tailoring. It’s fashion, but she makes it her own. TA

9. Susie Cave

Everyone who’s anyone has worn The Vampire’s Wife (Kate Moss, Sienna Miller, the Duchess of Cambridge to name a few), but the best ambassador for the brand is designer Susie Cave herself. A former model and muse to Vivienne Westwood, Bella Freud and Philip Treacy, Cave embodies the label’s feminine, ethereal Gothic glamour. Her best look this year? The showstopping gold gown she wore to collect a Leopard Award last month. TA

10. Gugu Mbatha-Raw

Like most actors of her calibre, Gugu Mbatha-Raw works with a stylist, and hers – Leith Clark – is one of the best. Championing British design talent like Roksanda, Emilia Wickstead and Galvan, their collaboration has resulted in a playful-yet-classic aesthetic that’s a breath of fresh air on what can otherwise be samey red carpets. TA

11. Maggie Gyllenhaal

It’s never quite clear whether Maggie Gyllenhaal’s rich velvet dresses and silk print shirts are made by a wildly expensive French designer, or plucked from the bargain bin of a thrift store in New York’s Lower East Side. That’s because the 44-year-old’s laid-back, comfort-first, print and texture-heavy look is wonderfully individual – and gets more interesting year by year. Melissa Twigg

12. The Duchess of Cambridge

The Duchess of Cambridge knows when to elevate her style, using clothing to create globally-resonant “wow” moments. Two particular ones come to mind in 2021; firstly, at the funeral of Prince Philip, the Duchess was poised and sombre in an impeccably tailored Catherine Walker and co. coat, accessorised with pearl jewellery from the Queen’s personal collection. Then there was this stunning Jenny Packham “Goldfinger” gown at the Bond premiere – a dose of much-needed high glamour post-lockdown. BH

13. Francesca Cumani

ITV’s racing correspondent Francesca Cumani always looks graceful and immaculate, no matter what the conditions, but it’s the extra thought that goes into the provenance of her wardrobe which really earns her a place on this list. Her stylist Sarah Kate Byrne is an advocate for sustainability so everything Cumani wears is vintage, sourced from charity shops or from small, mostly British designers who meet the duo’s high standards. BH

14. Carole Middleton

If you want a masterclass on dressing to flatter your figure after 50, look no further than Carole Middleton. Whether she is popping into Wimbledon, posing for a Christmas card or walking up the aisle of Westminster Abbey, Middleton has mastered the art of midlife dressing. And, impressively, is now even more of an LK Bennett wedge heel connoisseur than her daughter. MT

15. Rene Macdonald

Her parents worked as diplomats and she grew up between her native Tanzania and London. Both cultures run beautifully rampant in the way she dresses – bold, colourful but invariably tailored and disciplined. She’s vague about her age as she’s entitled to be. This is bold, beautiful ageless style. LA

16. Prue Leith

Bake Off was joyful for many reasons – one of them being Prue Leith’s absolute refusal to age quietly in biscuit-coloured knitwear. In canary yellow raincoats, scarlet shoes and bright pink dresses, she continues to inspire women of all ages. Not to mention her wonderfully cheerful accessories: bright eyewear, even brighter lipstick and bold jewellery. MT

17. Peneleope Knatchbull, Countess Mountbatten of Burma

Even amid the dignified elegance at the Duke of Edinburgh’s funeral, Countess Mountbatten stood out. No surprise there. She has been a quietly impeccable figure in the Windsor orbit for decades. The epitome of the mantra “buy once, buy well”, the 68-year-old Countess’s style has consistently leaned on expertly cut, understated classics that suit her. Judiciously chosen shirt dresses, tailored jackets, slim trousers and soft shades of blue interspersed with punchy pops of red ensure she always looks sleekly modern. LA

18. Aerin Lauder

Lauder’s olde worlde comportment and manners are a constant balm in a world where brash often seems to win out. Hugely influenced by her grandmother Estee, she grew up believing that when it comes to aesthetics, there is nothing that can’t be improved – rooms, table settings, hair – with a little work. Think tailored classics and timeless elegance. LA

19. Emilia Wickstead

Meghan and Kate are huge fans of Emilia Wickstead the brand, and some of the world’s most stylish brides have chosen to be dressed by the New Zealand designer. But Wickstead herself might still be the greatest brand ambassador of all. With her slicked back hair and minimal accessories, she looks dazzling in her colour block or print dresses, jumpsuits, and high-waisted skirts. MT

20. Priya Ahluwalia

The British menswear scene is being shaped by a group of talented young designers – led by Priya Ahluwalia. Although one glance at her own personal style proves she’d be a dab hand at womenswear as well. Ahluwalia draws inspiration from her Indian-Nigerian heritage and dresses in an array of slick suits, long print dresses and new-wave streetwear, much of which she designs herself. MT

21. Isabelle Huppert

Although she embodies classic French style, 68-year-old Huppert is also a daring adventuress in fashion-land. Her flame red hair and cinnamon coloured freckles ensure that even when she’s wearing the most pared-back black trouser suit, she never looks banal. But she’s also convincing when she’s twirling in a bat-like shroud on the Balenciaga catwalk, or staring down a phalanx of photographers at the Met Ball while dressed as a crimson mermaid. LA

22. Sanna Marin

Easily confused for an influencer – she could be a sharp dealer in the City – Finland’s 35-year-old prime minister is the youngest in the country’s history. She’s found an effective, sleek style that creates a big impact on the world stage without seeming either extravagant or inappropriately high maintenance. Well tailored, mainly monochrome separates (lots of trousers, obviating the problem of what tights and shoes to wear), sartorially she’s a manifestation of soft power. LA

23. Rosie Huntington-Whiteley

Huntington-Whiteley morphed from English rose girl-next-door to LA glamazon when she moved stateside. Now she’s back and has found her style sweet spot. It’s a lesson in glossy minimalism – she mostly sticks to a palette of browns, creams and black but is never boring with it, combining tactile textures like fluffy shearling or supple silk with sculpture-like accessories. BH

24. Marion Cotillard

Marion Cotillard at Cannes is French style personified. While other actresses are trussed up in tight gowns, she is often found in a simple navy shift dress, a pair of dungarees or a white linen skirt. Half her wardrobe is invariably made by Dior but even in couture, Cotillard exudes a very Gallic air of insouciance. MT

25. Leena Nair

Chanel’s new CEO proves you can look the part as a C-suite exec without sacrificing on style or femininity. 52-year-old Nair’s fashion formula relies on well-cut shifts in punchy colours that help her stand out in a crowd. They’re versatile, carrying her from meetings with world leaders at Davos to tea-picking in Kenya. It’s the uniform of a hands-on power player – Coco Chanel would surely approve. TA