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Fashionista's 31 Best-Dressed Celebrities of 2019

These celebs are leading the way for self-expression through fashion.

Billy Porter in Christian Siriano at the 2019 Oscars.

Red-carpet fashion generated a lot of buzz in 2019. While the ladies of Hollywood have always and will continue to look stunning, this year was a big one for menswear. Beginning with awards season and escalating at the camp-themed Met Gala, celebrities were given a chance — and became willing — to step out of the box and perhaps blur some lines of conventional gendered dressing. 

See: Billy Porter‘s tuxedo gown at the Oscars, Timothée Chalamet in Stella McCartney womenswear on the “Little Women” press tour and Harry Styles‘ painted nails for a few examples. In short, celebrity fashion in 2019 reshaped the cultural narrative around expressing oneself through personal style. 

Read on for our 31 picks for this year’s best-dressed celebrities who embodied personal expression, and credit where it is due to their talented and hard-working stylists.

Timothée Chalamet

Timothée Chalamet in Louis Vuitton at the 2019 Golden Globe Awards. 

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Timothée Chalamet’s red carpet style created a loud buzz this year and even inspired this amazing satirical essay about Chalamet’s stylist. But here’s the catch: he doesn’t have a stylist, which makes his unique sartorial decisions all the more impressive. Instead, he works closely with designers like Haider Ackermann. This year, the “Little Women” actor raised the bar for all other men sticking to the same black tuxedos on the red carpet.

Lizzo

Lizzo in Christopher John Rogers at the 2019 GLAAD Media Awards. 

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2019 was the breakout year of Lizzo, and now we can’t imagine a red carpet without her. Her outfits, styled by Marko Monroe, are always exciting, fun and Good as Hell, of course. The “Truth Hurts” singer loves a good ruffle and neon moment and always steals the spotlight at any awards show that she attends.

Lucy Boynton

Lucy Boynton in Miu Miu at the 2019 Venice Film Festival. 

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Lucy Boynton’s personal style never fails to impress. This year, the “Bohemian Rhapsody” actor worked with stylist Leith Clark and makeup artist Jo Baker to bring together her ultra feminine, mod-chic looks that I absolutely want to steal.

Tracee Ellis Ross

Tracee Ellis Ross in Christopher John Rogers at the POPSUGAR X ABC “Embrace Your Ish” Event. 

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Tracee Ellis Ross was our undisputed best-dressed celebrity last year, and this year is no different. It’s clear that the “Black-ish” actor is passionate about clothing — not just the way it looks, but the craft and design as well. Ross and stylist Karla Welch continue to leave us speechless year after year. 

Billy Porter

Billy Porter in Christian Siriano at the 2019 Oscars.

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Billy Porter, kindly remove your heels from our necks! The “Pose” actor has graced us with so many iconic and groundbreaking looks this year, from a tuxedo gown to a uterus-shaped ensemble (made from the “Kinky Boots” curtains) to support women’s reproductive rights. With his stylist Sam Ratelle, Porter has shaped the cultural narrative around gender-fluid attire this year.

Tessa Thompson

Tessa Thompson in Vaquera at the 2019 Film Independent Spirit Awards.

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I don’t think Tessa Thompson has ever made a fashion faux pas. She always looks elegant, yet young (I swear, this woman does not age). She’s not afraid to play around with fabrics, volume and color to create a fun-loving and glam outfit — with help from her stylists Wayman Bannerman and Micah McDonald, of course.

Zoë Kravitz

Zoe Kravitz in Tiffany & Co. bra top and Saint Laurent skirt at the 2019 Vanity Fair Oscar Party.

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Whether it’s an uber mini dress or 18k-gold bra top, Zoë Kravitz and stylist Andrew Mukamal consistently create the hottest looks on the red carpet. She looks equally as jaw-dropping in a vintage T-shirt and jeans as she does in Saint Laurent, her red carpet favorite. You can tell that everything she wears is true to her personal style.

Kristen Stewart

Kristen Stewart in Chanel at the “Seberg” premiere during the 2019 Toronto International Film Festival.

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Kristen Stewart has always valued red carpet comfort, but her looks felt more elevated and mature this year, from Chanel ensembles with sneakers to sexy suits with stilettos. Stylist Tara Swennen has helped Stewart find her red carpet footing and establish her style identity.

Zendaya

Zendaya in Nina Ricci at the LA Premiere Of HBO’s “Euphoria.” 

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Zendaya truly killed the game on- and off-screen this year. The multihyphenate’s “Euphoria” performance showed her depth as an actor, while her second Zendaya x Tommy Hilfiger clothing collaboration was a major hit in the fashion realm. With the help of her stylist Law Roach, Zendaya proved that delicate, sexy and sophisticated can be served simultaneously.

Margot Robbie

Margot Robbie in Rosie Assoulin at the Berlin photocall for “Once Upon A Time… In Hollywood.” 

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Margot Robbie’s style is decidedly sweet as can be. With help from stylist Kate Young, the “Once Upon A Time…In Hollywood” star went retro this year, channeling her character, Sharon Tate.

Kacey Musgraves

Kacey Musgraves in Valentino at the 2019 Grammy Awards.

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Yes, the red dress from the infamous Kacey Musgraves Grammys meme was worn just this year. With her stylist Erica Cloud, Musgraves is redefining country style, swapping out sundresses and cowboy boots for psychedelic tulle and sequins, but always with a nod to her roots — even if it’s literally just big hair.

Yara Shahidi

Yara Shahidi in Gucci at the 2019 LACMA Art + Film Gala.

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Yara Shahidi, 19-year-old “Grown-ish” and “Black-ish” actor, exemplifies how to be a teenager and have fun with fashion while still displaying an undeniable sense of elegance and maturity. With power stylist Jason Bolden, Shahidi has curated high-fashion red carpet looks that would make any college student jealous.

Sinéad Burke

Sinéad Burke at the Salvatore Ferragamo Dinner Party during Milan Fashion Week Fall/Winter 2019.

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Sinéad Burke made history this year as the first little person to attend the Met Gala. But more significantly, she’s an activist and self-proclaimed fashion-admirer, who is leading the way in making fashion more inclusive and available to all. In addition to being a powerful advocate, Burke has one of the most covetable wardrobes around, with some favorites being Gucci, Burberry, and Prada. 

Angela Bassett

Angela Bassett in Georges Chakra at the 2019 Screen Actors Guild Awards.

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With decades of work under her belt, Angela Bassett is still absolutely killing the fashion game with help from stylist Jennifer Austin. This year, she looked hot in a bright pink high slit dress at the Oscars and even wore a Chanel bra as a top.

Harry Styles

Harry Styles in a Lanvin cardigan at Spotify Celebrates The Launch of Harry Styles’ New Album.

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When Harry Styles isn’t in a dashing Gucci suit or glittery unitard, he’s probably wearing wide-legged trousers, a forbidden “Sex” T-shirt on national television or his well-loved black Vans sneakers. As always, Styles led the way for creative menswear this year with his stylist Harry Lambert (Harry squared, if you will). Fans and fashion-lovers alike have gotten to know and love Styles’ everyday style — painted nails, pearl necklaces and rings included.

Rihanna

Rihanna in Givenchy at Rihanna’s 5th Annual Diamond Ball. 

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While we miss Rihanna’s music career deeply, her fashion and beauty businesses have filled a void in our hearts. Although Riri is a certifiable fashion expert in her own right, she continues to work with stylist Jahleel Weaver, who is also a Fenty collaborator, to create her ultra-glam looks.

Sandra Oh

Sandra Oh in Stella McCartney at the 2019 Golden Globe Awards. 

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Christina Yang — I mean, Sandra Oh — had quite the year for style. The “Killing Eve” star co-hosted the Golden Globes earlier this year, where she wore three different gowns throughout the night, all by female designers. Oh is graduating from supporting role to leading lady, going from dark blue scrubs to glamorous, elegant gowns and suits with the help of stylist Elizabeth Saltzman.

Laura Dern

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I will not, not include Laura Dern in our best-dressed list! This year, Dern quickly became one of our favorite beauties to keep an eye out for on the red carpet, just like her “Big Little Lies” character Renata Klein became one of our favorite and most quotable on-screen personalities. Much credit goes to her stylist, Cristina Ehrlich.

A$AP Rocky

A$AP Rocky in Gucci at the Gucci show during Milan Fashion Week Spring/Summer 2020.

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A$AP Rocky and Gucci tweed blazer is a combination that we did not know we needed. The rapper was among the best-dressed front row guests at multiple fashion shows this year, showing his faithful interest in the industry.

Regina King

Regina King in Oscar de la Renta at the 2019 Oscar Awards.

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Oscar Award-winning actor Regina King is not only incredibly talented, but she’s also never killed it more on the red carpet than she has over the past year. With help from stylists Wayman Bannerman and Micah McDonald, King always stunts in sophisticated, shoulder-baring gowns.

Maggie Rogers

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Maggie Rogers’s fun-loving personality truly shines through her on-stage wardrobe, usually with some version of a free-flowing cape or scarf, wide-leg pants and booties that are made for dancing. The pop-folk singer just started working with a stylist this year, and now collaborates with Kat Typaldos for her wardrobe and designer Jinnah Park for her “Heard it in a Past Life” tour looks.

Chadwick Boseman

Chadwick Boseman in Atelier Versace at the 2019 NAACP Image Awards.

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Isn’t it crazy that Chadwick Boseman invented suits? Just kidding, but am I? Boseman has been working with menswear stylist Ashley Weston to transform his style. His fun and fresh ensembles — often by Givenchy, Versace or Ermenegildo Zegna — and streetwear-inspired everyday wardrobe were only some of the reasons he topped our best-dressed list this year.

Lady Gaga

Lady Gaga in custom Valentino at the 2019 Golden Globe Awards.

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Lady Gaga has always made over-the-top stylistic choices, which is exactly why the singer was a co-chair at the camp-themed 2019 Met Gala — and nothing is more camp than Gaga stripping down to her underwear on the Met steps at the biggest fashion event of the year. This year, Gaga worked with stylists Tom Eerebout and Sandra Amador to bring her intricate, multi-faceted looks together.

Lena Waithe

Lena Waithe in Grayscale at the 2019 NAACP Image Awards.

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There’s no other word that better describes Lena Waithe’s personal style than “cool.” Her casual looks and power suits always look like they were made just for her (and sometimes they were). Plus, Waithe is all about writing and performing in thought-provoking work, and that theme carried over into her personal style when she referenced and honored Black drag queens at the Met Gala with her Pyer Moss design.

Celine Dion

Celine Dion at the Schiaparelli Haute Couture Fall/Winter 2019/2020 show at Paris Fashion Week.

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My heart will not go on if Celine Dion and stylist Law Roach ever stop working together. After 30 years in the spotlight, Dion became an overnight fashion icon in 2016 when the pair started their collaboration. The looks that this dynamic duo create are always creative, unique and absolutely show-stopping.

Kiki Layne

Kiki Layne in Gucci at the 2019 LACMA Art + Film Gala.

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By virtue of stylists Wayman Bannerman and Micah McDonald, Kiki Layne always looks like she should have a red carpet rolled out in front of her. The “If Beale Street Could Talk” breakout actor is having a breakout moment in fashion as well, serving fun maximalist looks that even led to a campaign contract with Kate Spade.

Lili Reinhart

Lili Reinhart in Rodarte at the 2019 Time 100 Next gala.

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Lili Reinhart always manages to look equal parts sexy and sweet, thanks in part to stylist duo Brit and Kara Elkin, who also style Emma Roberts. 

Janelle Monáe

Janelle Monae in Marc Jacobs at the Janelle Monae x Instagram Fem The Future brunch.

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Janelle Monáe is no stranger to a funky silhouette. The multi-talented singer-songwriter-actor’s whimsical style always earns her a spot on our best-dressed list. At this point, she’s an expert in using style for personal expression.

Indya Moore

Indya Moore in Iris van Herpen at the 2019 Time 100 Gala.

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“Pose” actor Indya Moore has such a wide sartorial range. They can effortlessly pull off anything from a smoking-hot sheer top to a little white lace prairie dress. A passionate activist even when it comes to fashion, Moore created a social media frenzy when they wore earrings that honored the 17 Black trans women who were killed in the U.S. this year.

Henry Golding

Henry Golding in Tom Ford at the 2019 Screen Actors Guild Awards.

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Ever since he skyrocketed to fame last year, Henry Golding has been dressing a whole lot like his sharply styled characters from “Crazy Rich Asians” and “A Simple Favor.” This year, he graduated from black, white and navy blue suits to velvets, florals, sequins and more than one plaid look for the winter to promote his holiday film, “Last Christmas.”

John Legend

John Legend in a Paul Smith suit and Prada shirt at the Los Angeles premiere of HBO’s “United Skates.”

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John Legend, also known as Chrissy Teigen’s husband, can rock a suit in any velvet, pastel or jewel tone that he likes. The singer-songwriter was voted People‘s Sexiest Man Alive 2019, and it’s clear that his style played a factor in earning him the title. He and his stylist, David Thomas, are constantly reinventing the classic suit, whether it’s by adding a ruffled Prada button-up shirt or pairing the look with white Celine boots.

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Source: Fashionista.com

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