The 25 best-dressed women of the year - and they're all over 40
Princess Caroline of Monaco, 63
The big fashion moment of 2020 for Princess Caroline came in November when she attended Monaco’s National Day celebrations wearing a black Chanel suit, her hair swept back with a plaited Alice band which subtly highlighted her softly grey roots. Of course, this is how Caroline, an under-the-radar princess who has always stuck to timelessly chic looks with just a dash of edge, would style out going silver. BH
Alexandra Tolstoy, 46
The trend which dominated 2020 was cottagecore and the person who embodied it for grown-ups was Countess Alexandra Tolstoy, who spent her lockdown in the Oxfordshire countryside with her three children, wearing a constant rotation of haute-peasant blouses, floral dresses and homespun knitwear. She may now be back in London, but the prairie chic inspiration continues with capes for church and embroidered jumpers for supper at home. BH
Rene Macdonald, 50
Bold prints and vibrant colours don’t always seem to equate with elegance in modern fashion parlance, but Rene Macdonald – founder of the label Lisou – offers a masterclass in looking sophisticated whilst experimenting. Macdonald, who grew up in Tanzania, makes light work of clashing, say, an emerald diamond patterned blouse with high-waisted trousers embroidered with silver flying women. Even the Duchess of Cambridge is taking cues – she wore a Lisou rainbow blouse in October. BH
Jet Shenkman, 59
Jet Shenkman’s label Eponine specialises in couture occassionwear, but the designer has an effortless and joyful way of styling herself which really resonated this year. The essential elements of her look? A fabulous Eponine fit-and-flare dress or neat dog-tooth suit paired with a statement yet practical pair of shoes (Vans are a favourite) plus an exuberant hair accessory and chunky tortoiseshell glasses. BH
Helena Morrissey, Baroness Morrissey, 54
Helena Morrissey has long been hailed as the ultimate modern power dresser, a woman who juggled being a chief executive in the finance industry with being mother to nine children. But how did she face a year in which the notion of workwear was turned on its head? She gave practical tips on keeping up WFH morale and dressing for video calls, as well as taking the chance to showcase pieces from her incredible wardrobe – a series of Instagram posts were dedicated to her wearing ball gowns in her garden. BH
Kristin Scott Thomas, 60
Britain’s favourite French-ish actress (she’s lived there since she was 19) deserves a permanent spot on any best-dressed list. Few women wear a tuxedo with as much panache as Thomas, and she suits other forms of tailoring, too – she was the one upside of an otherwise unremarkable Rebecca, chilling as the sharp, severe, skirt-suited Mrs Danvers. She’s also prescient: the long-sleeved gold dress she wore to the premiere of Military Wives would be just the thing to wear for a relaxed but gleaming Christmas on the sofa. EC
Claudia Schiffer, 50
What does 50 look like now? According to the supermodel Claudia Schiffer, who celebrated her milestone birthday in August, it’s wearing an electric blue, sheer crochet dress while counting up Instagram “likes”. Designers including Dolce & Gabbana and Donatella Versace launched new products in honour of Schiffer’s 50th. During the year’s lockdowns, her regular outfit posts have been fun to follow – as well as the party dresses, she does a lot of good, practical denim looks too. CL
Kamala Harris, 56
Madame Vice President has a nice ring to it, doesn’t it? In a year that has been disappointing at best, the election of US President-elect Joseph Biden and Vice President-elect Kamala Harris stood out as a bright spot. Harris’s ascendance is historic for so many reasons – including interest in how the US’s first female VP will remake the second-highest office in the land in her own image. Expect modern tailoring, statement pearl necklaces and the right shoes – Converse trainers or Manolo stilettos – for every occasion. EC
Gabriela Hearst, 44
It has been a mega year for Gabriela Hearst. Not only were dresses by the Uruguayan-American designer worn during the US Presidential campaign by both Dr Jill Biden and Ivanka Trump, earlier this month she took on the prestigious role of creative director of Chloé. Hearst herself dresses beautifully in the sort of ultra-luxe monochrome and expensive accessories favoured by the 0.1 per cent – although be warned, all of her outfits will instill in you a deep yearning for a world of parties and champagne receptions. One day… MT
Yvonne Telford, 47
Designer and founder Yvonne is her own e-commerce model, much to the delight of her label’s loyal following (@kemitelfordqueens). Not that her statement Kemi Telford printed frocks need accessories, but Telford herself nails it with sculptural earrings, printed cardigans and heeled boots or chunky trainers, depending on her mood. She only designs what she’d happily wear herself, and the proof is in the pudding: rarely is the designer not pictured smiling from ear-to-ear in a joy-bringing frock. KT
Christiane Amanpour, 62
English-born Amanpour has stylish workwear down pat. In a year that saw the rest of us set our tailoring aside for luxe loungewear and cashmere socks, for CNN’s Chief International Anchor, the show went on. She toed the fashion/formal line perfectly, opting for velvet trousers and blouses, or tailored suits with cinched waists and boot cut trousers that sat nicely over her leather boots. The war reporter and anchor isn’t afraid to love fashion, and breaks the assumption that you can’t be intelligent and successful and care about what you wear. KT
Paula Sutton, 50
Paula Sutton lives a picturesque life on Instagram that’s different to many of the clichés – there are no skyscrapers or champagne receptions in sight, but rather a Georgian house in Norfolk that acts as a backdrop for tea parties, gardening and laying beautiful tablescapes. Sutton is doing Jane Austen style for now, lifting the mood with her chintzy frocks and wellies. Anyone who thinks the countryside isn’t cool just needs to stumble upon Sutton’s secret garden. HM
Maria Grazia Chiuri, 56
The creative director of Dior didn’t let the mere fact of a pandemic dent her style, sticking to her usual immaculate uniform of monochrome dresses, simple shirts and well cut trousers over the rollercoaster of the past 10 months. Conducting most of her interviews for her latest collections in impeccably cut navy jumpers and denim, her hair slicked back into a ponytail, Chiuri is minimalist to the core – and the perfect role model for anyone looking to start 2021 in the sleekest way possible. MT
Tory Burch, 54
Tory Burch was always going to make the year of staying home look good. She dabbled in aspirational interiors before 2020 (her lettuceware is the stuff of crockery dreams), and the year’s homebound vibe provided the perfect opportunity for her to hunker down in style. So Burch leaned into designer dog-walking attire (Chicken and Slim, we love you), cosy-luxe fireside outfits (knitwear galore) and stay-at-home sequins (an all-yellow outfit looked as good on her as it did in her brand’s New Bond Street boutique window). Bravo, Ms Burch. EC
Catherine O’Hara, 66
The world has fallen head over heels for Moira Rose from Schitt’s Creek, played by Canadian actor Catherine O’Hara. As the matriarch of a family that’s gone from riches to rags, Moira lives vicariously through her designer labels: Balenciaga, Isabel Marant, Alexander McQueen and many more. In real life O’Hara is just as OTT, with sequins and glitter being the name of her fashion game. HM
Linda V Wright, 72
Forget Emily in Paris, the fictional Netflix series which obsesses over whether a 20-year-old publicist from Chicago can discover French chic. Turn your attention to Linda in Paris; 72-year-old Linda Wright has been “doing an Emily” in real life since 1978, when she relocated from Texas. Wright is the director of Crimson cashmere boutique on Rue Marbeuf and has a refined yet joyful sense of style. Her daily posts have documented her year in colourful, cheering knitwear and have kept 120,000 Instagram followers inspired. CL
Uberta Zambeletti, 52
Working from home in burgundy leather trousers? Cooking a lockdown risotto in scarlet sequins? These are just some of the style scenarios realised by Uberta Zambeletti in 2020, a woman who has not let her sense of fashion fun slip an inch because of the pandemic. The founder of the Wait and See concept store in Milan, Zambeletti favours a palette of red, orange, gold and leopard print. Ideally? All at the same time. Not once did Zambeletti succumb to a grey tracksuit… CL
The Duchess of Cornwall, 73
When Camilla stepped out in a leopard-print mask and a chic monochrome outfit in October, she caused a stir on social media, with fans of all ages pointing out that despite being in her seventies, she can still give the younger Duchesses a run for their money. Camilla had worn the pinafore dress by couturier Fiona Clare before and this time paired it with a white silk balloon-sleeve blouse and a cape from the same brand, and finished the look with suede boots that wouldn’t have looked out of place in a fashion magazine. MT
Queen Elizabeth II, 94
Her Majesty understands the power of her image perhaps better than anyone else on the planet. Therefore in this particularly testing year, a glimpse of the Queen in a reassuring colour – or an uplifting one, a festive one, or one which harmonises with the uniforms worn by the NHS – can speak volumes to a worried public. Her Majesty nailed it again and again, but this striking rose pink outfit, worn in October for her first in-person engagement since the start of the pandemic, was particularly lovely. CL
Gillian Anderson, 52
Raise your hand if you have been cheered up by the mere sight of Gillian Anderson this year. Whether it was her turn as bejewelled-dress wearing Jean Milburn in Sex Education, as blue-suited Margaret Thatcher in The Crown, or silk blouse wearing Stella Gibson in reruns of The Fall, she was never not a tonic for our eyes. Her Instagram posts were equally cheerful, with outfits ranging from Khaite shirts to slim tracksuit trousers, racing green shirts… and Dune fluffy slippers. Finally, an outfit we can copy for 2020. MT
Nancy Pelosi, 80
Nancy Pelosi: influencer? The Speaker of the House made fashion waves last year when the popularity of her red MaxMara coat compelled the house to reissue the style. This year, she applied her powers of persuasion to masks. She was among the first politicians to embrace mask-wearing and its accessorising potential, choosing masks that picked up on the colours or patterns of the bright suits and dresses she wore to work at the US House of Representatives. In the process, she normalised or demystified mask-wearing for millions. EC
Queen Maxima, 49
Queen Maxima of the Netherlands serves up all the glitz and glamour we’d expect of a Queen. Dubbed “Maxima the Maximalista” by this publication, in a year where everything was scaled back, Maxima – known for her rainbow wardrobe, power dressing panache and excellent accessorising game – dialled it right back up. Her most fabulously OTT 2020 look? A tangerine midi dress, with tan suede courts, sunglasses and a top handle bag – for riding a bike on a visit to south-east Friesland, naturally. KT
Dr Zoe Williams, 40
Dr Zoe Williams is the most stylish doctor on TV. There are no shift dresses or ballet flats in sight, instead it’s considered silky blouses and leather skirts that elevate this GP’s look. Williams unashamedly makes her love of fashion work for her day job. When duty calls she’s in her blue scrubs, but on air she has an affinity for comfortable yet unexpected fabric combinations that cement her as a standout hit on the small screen. HM
Patti LaBelle, 76
Patti LaBelle has not let a pandemic dim her light – of course, no real diva would ever let that happen. At 76, she has kept up her style mojo in geometric prints. Her signature diamanté hoop earrings and purple acrylic nails can be relied on to lift spirits wherever she is, be it performing to an empty audience at a Thanksgiving parade or hosting impromptu cooking tutorials on Instagram. If you want to be more LaBelle, just dress with some soul. HM
Dame Donna Langley-Shamshiri, 52
As Chairman, Universal Filmed Entertainment Group, Dame Donna Langley is often the sole woman among a sea of men, but that doesn’t stop Hollywood’s first lady plumping for the most feminine of looks. Pictured here at a film premiere back in February (remember those?), the British-born film executive wore a printed midi dress and sleek knee-high leather boots – her go-to polished, but effortless, outfit formula – complete with her trademark curls. KT
