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Art of Style

2019’s best dressed

Over the past 12 months, we have been compiling the definitive guide to this year’s best dressers. It was near impossible to narrow our sartorial love list down to just 25 unequivocal style winners, but we got there in the end. So, from the red-carpet show-stoppers to the icons of cool, here are the incredible women whose looks we have swooned over in 2019…


Katie Holmes

Katie Holmes and her subtly sexy ‘bradigan’ was the viral fashion moment of 2019. Epitomizing the sartorial shift away from streetwear as the fashion world indulges in a new fascination with the ’70s Bourgeois trend, Holmes and her coquettish cardigan reminded us to never underestimate the sex appeal of a luxe knit, some artful layering and just the right amount of exposed skin. The biscuit-colored top in question was by emerging New York-based label Khaite and the actor has since been spotted out in many more of the brand’s elevated basics, from a fringed suede jacket to pair of zebra-print knee-high boots. Striking the perfect balance between aspirational and accessible, we’ll be keeping a close eye on Holmes’s chic make-under next year.

Zoë Kravitz

As the daughter of rock royalty Lenny Kravitz and ’90s icon Lisa Bonet, coolness was a birth right for Zoë Kravitz. Her personal style hits the sweet spot between downtown LA grunge and vampish Parisian nonchalance, as she wears boldly-colored and baggy silhouettes just as well as she rocks micro-mini, second-skin dresses. It was for precisely this reason that Saint Laurent’s Anthony Vaccarello tapped the sultry-eyed beauty as a brand ambassador. Reprising her role as earth-mother Bonnie in HBO's critically acclaimed series Big Little Lies for a second season, she slinked down the red carpet at the show’s New York premiere wearing a sequinned black Saint Laurent mini dress, reminding us why she’s Hollywood’s archetype cool girl. For the Oscars after-party, she chose a barely-there, gold Tiffany bra top with a black, floor-skimming Saint Laurent skirt, proving that she’s not afraid of taking risks on the red carpet either.

Jennifer Lopez

It’s no stretch to say that 2019 was Jennifer Lopez’s year. From getting engaged to boyfriend, now-fiancé, Alex Rodriguez in March to celebrating her 50th, yes 50th, birthday in July with a lavish party in Miami and releasing box office smash Hustlers in September, Lopez has cemented her status as a pop-culture icon. However, the highlight of her year was undoubtedly closing the Versace SS20 show at Milan fashion week in an even more risqué version of the legendary jungle-print dress that she wore back in 2000. While the original outfit is credited with creating Google Images, thanks to the furore and frenzied searches it inspired, this time around, suffice it to say, Lopez broke the internet.

Victoria Beckham

The perfect poster woman for her elegantly understated fashion house, our perennial style crush, Victoria Beckham, never puts a stiletto-clad foot wrong. The pieces she wears are simple but exquisitely crafted. From perfectly cut wide-leg pants and plush knits to crisp shirting and endlessly wearable midi skirts, her closet is full of classic pieces with a contemporary twist – making her look both timeless and utterly of-the-moment. Unsurprisingly, this sartorial prowess extends to accessories too. We’re particularly besotted with the peep-toe boots VB has been sporting this year. However, it was Beckham’s tailoring that truly stole the show in 2019. On multiple occasions (and in multiple colors), she has proved that she can rock a tux like the best of them.

Phoebe Waller-Bridge

2019? Phoebe Waller-Bridge completed it with her Emmy hat-trick for the darkly comedic Fleabag – which she wrote, produced and played the lead in – not to mention her other accolades this year, such as the ongoing success of Killing Eve (the Bafta-winning drama she co-wrote) and the American Vogue cover she rounded off her stellar year with. Waller-Bridge brings her idiosyncratic touch to her personal style, too, and the fashion world is just as enamored with this hyper-achieving multi-hyphenate as the TV critics. To collect the gongs, she wore a glittering Monique Lhuillier gown, perfectly fit for the Hollywood star she has so deservedly become.

Cindy Crawford

Cindy Crawford continues her reign as the queen of model off-duty chic with a street-style closet that is one part all-American woman and one part executive realness. Case in point? The asymmetric Max Mara suit Crawford recently sported on the streets of New York, finished with this season’s must-have barely-there sandals and a ladylike top-handle bag. The original supermodel’s flawless style formula is timeless, effortlessly elegant and something we’ll be applying to our closets in 2020.

Adwoa Aboah

As a fearless dresser who dares to experiment with color, the joy of Adwoa Aboah’s style is that it’s always unpredictable yet always completely her. Off-duty, the model’s hi-lo approach to dressing has made her a street-style favorite. Consider the baby pink Molly Goddard dress she debuted during London Fashion Week: Aboah served up pure originality by styling the look with a vintage-inspired Gucci bag and cat-eye sunglasses that gave it a playful twist. The model’s uncanny ability to take a trend and make it feel entirely her own is a true fashion superpower.

Deepika Padukone

As the Bollywood star who breathes life into our wildest fashion fantasies, Deepika Padukone is unparalleled in her ability to make magic on the red carpet. This year, her sartorial highlights are a whirlwind of enchanting couture pieces. However, it was at the Cannes Film Festival that Padukone truly took mega-watt glamour to another level, in a tulle Giambattista Valli masterpiece that brought the red carpet to a standstill – and made headlines around the globe.

Jodie Comer

From pussybow blouses at Saint Laurent to slouchy suiting at Versace, a less-is-more approach proved itself to be the most modern way to stand out on the red carpet this year. Few mastered it quite as deftly as Jodie Comer. The Killing Eve star’s stand-out look of the year was undoubtedly the Grecian-style white gown she wore to collect her first Emmy Award. Designed by Tom Ford, this knock-out dress featured long sleeves and a full-length skirt – albeit with a sensational thigh-high slit and plunging neckline.

Rosie Huntington-Whitely

As the woman who pioneered sleek airport style, Rosie Huntington-Whiteley has pared back elegance down to a tee. Her sartorial formula relies on luxe, well-cut pieces in an easy to mix color palette of cool neutrals. As the fashion world collectively fell head over square-toed heels for Bottega Veneta this year, Huntington-Whiteley showed us how to wear this big-love label on the street: that purple dress with its ultra-modern sweetheart neckline, those dreamy cloud-like pouch bags. Another of her winning looks of 2019 put a subversive spin on classic tailoring: a camel coat shrugged nonchalantly over a matching tonal knit with black tailored pants tucked into Jimmy Choo’s cult mock-croc Mavis boots and finished with a chunky chain. It’s easy to see why she’s the reigning queen of refined off-duty style.

Letitia Wright

When it comes to tailoring, Letitia Wright is a one-woman masterclass in the art of chic suiting. The Black Panther star’s signature esthetic is defined by clean lines, sleek cuts and streamlined accessories, making her the poster girl for androgynous sophistication. Wearing a precision-cut white tuxedo by Stella McCartney to accept her Rising Star award at the Baftas, Wright cemented her status as one to watch on the red carpet and rekindled our love affair with the sleek simplicity of after-dark suiting.

Martha Hunt

Walking for some of the biggest names in fashion might have made Martha Hunt the American model of the moment, but it’s her phenomenal personal style that has made her an icon – and earned her an Instagram following of over three million. Unafraid to experiment with color, Hunt excels at tonal dressing, regularly making head-to-toe mustard yellow, beige, navy and emerald green look effortless. A champion of female-led labels such as The Row, Khaite and Matteau, her minimal look is a daily source of sartorial inspiration.


At just 22, Zendaya’s reign as a noughties style icon is firmly in ascent. A devoutly fashion-forward dresser, the actor and singer is always pleasingly experimental with her style – it would be quicker to list the styles and looks that she hasn’t yet tried than the ones she has. She is clearly a woman who truly loves fashion and, as well as donning couture gowns by Armani Privé on the red carpet, she also champions emerging designers such as New York-based newcomer Peter Do. We can’t wait to see what this fearless fashion chameleon pulls out of the bag next year.

Lupita Nyong’o

When it comes to getting dressed, many women shy away from riotous prints and eye-popping colors, but Oscar-winning actor Lupita Nyong’o is not one of them. In fact, it’s her fearless approach to styling that has the fashion world enthralled. This year, as ever, she has served up innumerable mood-enhancing looks – sequins, polka dots, vivid colors – you name a trend, she’s tried and conquered, it. But, of course, Nyong’o’s genre-defying Met Gala gown deserves a special shout-out of its own. Designed by Donatella Versace, who fully embraced this year’s ‘camp’ theme, the star-strewn, technicolor creation was a knock-out. By crowning her look with a gilded afro, Nyong’o brought black-girl magic to the red – or this case, pink – carpet.

Liu Wen

It’s hard to overstate the impact Liu Wen has had on the fashion industry. From becoming the first Asian model to land on the Forbes list of highest paid models to being unveiled as Estée Lauder’s first Asian spokeswoman, she’s been making history since day one. As one of the most sought-after names in the game, it should come as no surprise that Wen still dominates the runway. However, it’s her personal style that really has us enthralled. Eschewing the tired biker-jacket-and-skinny-jeans model off-duty look, Wen’s elegant yet androgynous esthetic feels like a totally fresh proposition. A fan of straight leg jeans, she often pairs them with everything from boyish brogues and oversized blazers to sneakers and tie-dye tees. Trying to perfect your weekend wardrobe? Take note.

Sienna Miller

Sienna Miller’s style has evolved over the years without ever forsaking her boho-chic heartland. Lately, she’s been stepping out in sleek silk separates by female-led labels such as Nili Lotan and The Row. Her penchant for relaxed denim prevails, and for good reason too – no one makes vintage jeans look quite as elegant as Ms Miller. Slouchy suiting, demure evening dresses and tonal layers are also defining features of the actor’s sartorial evolution, striking the perfect balance between laidback and polished. If you want to recreate her look, the key is to never scrimp on accessories – think statement earrings, retro cat-eye sunglasses or shoes in an unexpected pop of color.


With a Billboard 100 record-breaking single under her belt, 2019 has been the year of Lizzo. Looking ‘good as hell’ on and off the stage, the singer’s maximalist style is a like a love letter to the art of dressing for yourself. When performing, an array of lingerie-inspired bodysuits has become a highlight of her high-energy concerts. This fearlessness extends to the red carpet too, where Lizzo is unafraid to make a statement with bold splashes of color and headline-grabbing accessories. Take the internet-breaking outfit she wore to this year’s American Music Awards: Lizzo’s bright orange, ruffled mini dress was eclipsed only by the diminutive Maison Valentino handbag dangling from one perfectly manicured finger.

Ashley Olsen & Mary-Kate Olsen

You’d be hard-pressed to find a Best Dressed list that doesn’t feature this ultra-stylish duo – and for good reason, too. Not much has changed since their oversized-hobo-bag-plus-venti-latte heyday, and the sisters and co-creative directors still serve up their trademark insouciance via oversized tailoring, louche robe coats and expertly tousled waves. As the poster girls for the discreet luxury esthetic behind their cult label, The Row, follow their lead to perfect the art of understated sophistication.

Kaia Gerber

Next-gen ‘Super’ Kaia Gerber might have turned 18 in September this year, but it was back in June, when the model called upon legendary hair stylist Guido Palau to give her a dramatic new look, that her style really went up a notch. The ‘drama cut’ gave Gerber’s ’90s-inspired off-duty uniform (think straight leg jeans, leather jacket, crop tops and, of course, Matrix-style sunglasses) an entirely new edge. However, it’s not just Gerber’s out-of-office style that excels – she has also expanded her arsenal to include an array of chicly tailored pieces. Case in point, the precision-cut, khaki Alexander McQueen skirt suit she was recently spotted in.

Rooney Mara

The undisputed master of monochrome dressing, actor Rooney Mara is living proof that, despite what your Instagram feed might lead you to believe, there is room for understated elegance on the red carpet, even in 2019. A regular fixture on this year’s festival circuit, she dazzled in a myriad of enchanting gowns. From suitably gothic lace dresses to graphic two pieces and embellished jumpsuits, Mara proved that quiet luxury can be just as impactful as the most outré ensemble. We were particularly enamored by the white Givenchy Couture gown she wore to the Joker premiere in Venice; finished with minimal makeup and a chic topknot, Mara resembled a modern-day Audrey Hepburn.

Margot Robbie

Margot Robbie is a dab hand at bringing her personal brand of modern bohemia to the red carpet. The Australian actor’s go-to look is a billowing maxi dress with minimal accessories and glossy beach waves, and she gravitates to brands associated with high summer, such as Jacquemus and Zimmermann, or ultra-feminine, frothy gowns by Rodarte. Off-duty, her look revolves around pared-back denim and low-key blouses. Robbie is the ultimate go-to for girl-next-door-meets-grown-up-glamour.

The Duchess of Cambridge

No matter the occasion, you can always be sure that the Duchess of Cambridge will be bring a sense of ceremony with her polished personal style. This year, as ever, she dazzled in an array of timeless looks – from her flawless take on off-duty dressing (think Breton stripes paired with perfectly tailored pants and playful accessories) to her signature skater-style coats and a particularly joyful floral dress by British designer Emilia Wickstead. All of which she accessorized with her mega-watt smile and perfectly coiffed mane.

The Duchess of Sussex

2019 has been another year of iconic looks for the fashion-forward Duchess, who turned maternity dressing into an art form, showcasing an enviable array of power pieces by Valentino, Carolina Herrera and Alexander McQueen. She also made a strong sartorial statement with a nod to sustainability by re-wearing the same elegant purple midi dress for, not one, but two royal engagements. Reminding us that that truly great design is made to be worn, and cherished, forever.

Priyanka Chopra Jonas

Striking the perfect balance between fun and refined, Priyanka Chopra Jonas’s modern take on feminine dressing has enlivened red carpets, talk shows and, of course, our Instagram feeds, throughout 2019. A champion of color, print and sparkle, Chopra Jonas never shies away from a scene-stealing ensemble. With a penchant for waist-cinching dresses, ladylike coordinates and vertiginous heels by designers such as Max Mara, Michael Kors and Christian Louboutin, it’s Chopra Jonas’s ability to wear these elevated pieces with a sense of ease that makes her style so alluring.

Tracee Ellis Ross

Known for her love of vivid colors, daring cuts and exaggerated proportions, sartorial alchemist and actor Tracee Ellis Ross is a true champion of avant-garde fashion. Therefore, when the news broke back in October that she would host the UK’s 2019 Fashion Awards, the announcement was met with a rapturous reception. Fans were hoping that Ellis Ross would serve up some serious red-carpet showstoppers, and she did not disappoint. From a white handkerchief dress by Loewe and Richard Quinn’s signature prints to not one but two sensational sequined dresses, designed by Simone Rocha and Gucci, plus a dramatic brocade ensemble, courtesy of Erdem. As ever, Ellis Ross brought an air of fantasy and fun to the ceremony.

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