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We're Calling It: These Are the 50 Best Dressed Women of 2019

Whether they're hitting a red carpet or re-inventing how to wear a cardigan, this year's style stars have really stepped things up.
Oct 14, 2019 @ 9:00 am

We’ve walked the red carpets, scrolled through the feeds, and scored the street style shots, and the verdict is finally in: this year in fashion was all about individuality.

Lady Gaga went both movie star glam at the Oscars and full-on fashion transformer at the Met Gala. Brie Larson channeled her superhero alter ego throughout her entire Captain Marvel press tour. And Zoë Kravitz showed us that, yes, an 18-karat gold bra can look just as chic as a ballgown on the step-and-repeat.

For fashion lover Tracee Ellis Ross, the fashion process was actually pretty simple this year. “The secret is to embrace your own style and try not to follow trends,” she says. That style M.O. was on display at the Met Gala’s celebration of camp fashion when she wore a black Moschino dress, complete with a gold picture frame around her face, paying tribute to black art. “The gold frame I wore was to open everyone’s eyes to the contributions that black men and women have had on camp fashion. It was an ode to the artist Lorraine O’Grady.”

Elle Fanning, who fronts InStyle’s November “Best Dressed” issue, also lands on our list for her love of fashion fantasy. “I love feeling confident in what I’m wearing,” says Fanning, who had a near constant rotation of frothy, fabulous princess dresses this year by Kimhekim, Rodarte, and Vivienne Westwood Couture, among others.

Tessa Thompson followed one major piece of fashion advice when she was getting ready for the red carpet this year. “Dress how you want to feel, not for how you want to look,” she says. “It makes getting dressed up an absolute dream, and also a party, a celebration, an adventure, a risk — all the good things in life.”

Keep scrolling to see our complete list of the 50 best dressed stars of 2019.

For more stories like this, pick up the November issue of InStyle, available on newsstands, on Amazon, and for digital download Oct. 18.

1. Cate Blanchett

Courtesy of Morag Ross

Her go-to look may be “a well-pressed suit,” but even when she opts for something wildly glamorous, Blanchett (in Fendi Couture) keeps it real—fashion critics be damned. “True chic is effortless, and it’s got to come from you,” she says. “It’s not about what gets likes and views.”

 

2. Kate Bosworth

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In Chloé at Build Studio in N.Y.C.

 

3. Zoë Kravitz

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“At first I was like, ‘There’s no way in hell I’m wearing that.’ Then I sent my mom [Lisa Bonet] a picture of it as kind of a joke. And she said, ‘Honestly, you can only wear that for a few more years, so if you’re going to do it, you should do it now,’” says Kravitz of her statement-making Tiffany & Co. Elsa Peretti bra and Saint Laurent by Anthony Vaccarello skirt at the Vanity Fair Oscar party.

 

4. Nico Parker & Thandie Newton

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Not only did Thandie Newton (in Oscar de la Renta) pass along her passion for acting to her 14-year-old mini-me (and breakout star of Dumbo), Nico Parker (in Gucci), she also showed her the red-carpet ropes this year. Turns out, artful draping, playful patterns, and feminine flourishes are winning at any age.

 

5. Issa Rae

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“I’m not the biggest fan of red carpets, so when I do go, I like to have fun,” says Rae (in Peter Pilotto), who has been turning heads with her punchy color combos. “Bold colors match my personality, and, quite frankly, they look best on my skin tone.”

 

6. Julianne Moore

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Ever wonder how Moore always looks camera ready? She checks her angles long before she leaves the house. “The best thing that’s happened to me regarding fashion is the iPhone,” she jokes. No doubt this gleaming Valentino creation earned its spot on her camera roll.

 

7. Lupita Nyong'o

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In Honayda at the Us premiere at the SXSW Film Festival in Austin.

 

8.Michelle Pfeiffer

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In The Row at the D23 Expo in Anaheim, Calif.

 

9. Saoirse Ronan

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In Gucci at the Golden Globes in L.A.

 

10. Elle Fanning

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It’s safe to say Fanning (in Rodarte) has a thing for pink. But no matter what color she’s wearing, the 21-year-old star shines brightest in looks that play up her love of fashion fantasy — the more bows, beading, and ball gowns, the better.

 

11. Tracee Ellis Ross

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If you follow Ross (in Rodarte) on Instagram, you already know the Black-ish star likes to keep things playful (can you say bathtub chic?). Thankfully, she brings that same joie de vivre to the red carpet. “The secret is to embrace your own style and try not to follow trends,” she says. “I feel an immense sense of freedom when I express myself through fashion.”

 

12. Naomi Watts

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In Nina Ricci at the New York Film Critics Circle Awards.

 

13. Jennifer Aniston

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In Celine by Hedi Slimane at the L.A. premiere of Murder Mystery.

 

14. Adwoa Aboah

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In Diane von Furstenberg at the Met Gala in N.Y.C. 

 

15. Brie Larson

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“Captain Marvel is a force who owns her power, so we wanted Brie’s red-carpet looks to reflect that,” says stylist Samantha McMillen. This year, Larson (in Celine by Hedi Slimane) gravitated toward sleek lines, sequins, and accessories that pack a punch.

 

16. Lucy Boynton

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During her awards-season sweep for Bohemian Rhapsody, Boynton leveled up her style game. “I loved this Gucci look because it was the peak of my experimentation,” she says. “You would’ve never caught me in that a year ago.”

 

17. Céline Dion

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No one does cheeky street style quite like Dion. This summer she turned the City of Light into her personal runway, giving everything from a Vetements “I Love Paris Hilton” T-shirt to Chanel spandex a moment in the sun (above).

 

18. Tessa Thompson

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“My best piece of style advice? Dress for how you want to feel, not for how you want to look,” she says. "My favorite look this year was the custom dress that Rodarte made for my Men in Black: International premiere. They dressed me for my first big premiere, so this felt like a full circle moment."

 

19. Nicole Kidman

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The best part about Kidman’s style? You can never quite predict what she’ll step out in next. Whether she chooses an architectural sheath or a sequined turtleneck gown (in Michael Kors Collection), the red-carpet pro still manages to surprise us year after year.

 

20. Chloë Sevigny

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In Miu Miu at the Cannes Film Festival.

 

21.Megan Rapinoe

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In Coach 1941 shorts at the ESPY Awards in L.A.

 

22. Ruth Negga

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In Louis Vuitton at the Venice Film Festival.

 

23. Laura Harrier

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“I got to play dress-up all year!” says Harrier (in custom Louis Vuitton), who calls her first awards season [for BlacKkKlansman] a total whirlwind. “I’m a ‘T-shirt and jeans’ girl most of the time, so it was definitely a step outside my normal life.”

 

24. Yara Shahidi

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“I’ve had so much sartorial fun this year,” says Shahidi, who lists the Monse look she wore to the CFDA Awards among her most memorable. To find her groove, Shahidi keeps a “growing album of inspirational images” that ranges from street murals to protests to iconic shots of Naomi Campbell. “My stylist Jason [Bolden] and I use every moment to explore a new aspect of my fashion sensibilities.”

 

25. Janelle Monáe

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In Marc Jacobs at Instagram's "Fem the Future" brunch in L.A.

 

26. Gemma Chan

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In Miu Miu at the InStyle and Warner Bros. Golden Globes after party in L.A.

 

27. Danai Gurira

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In Thom Browne at the brand's fall show in Paris.

 

28. Elizabeth Debicki

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With her relaxed way of styling (she wears suits with a silk blouse or, you know, nothing at all), she’d top our list even if she simply stuck to separates. But when she does go off script — like in her maximalist floral Armani Privé number (above) — it’s pure fashion magic.

 

29. Kiki Layne

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Though Layne is relatively new on the scene, she has quickly made her mark. “This year has been filled with so many fashion firsts, including my first Met Gala and the first time I had a gown custom-made for me [at the Golden Globes, above],” says Layne. “I’m excited to keep surprising people.”

 

30. Sarah Paulson

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“Sarah’s style is the perfect mix of femininity, strength, and full-on fashion,” says stylist Karla Welch of the star (in Prada).

 

31. Lady Gaga

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Whether she’s channeling Old Hollywood with an Oscar in hand or going full-fashion transformer with four Met Gala looks, one thing remains constant: her go-to designer and longtime pal Brandon Maxwell. “The world sees the moments on a carpet, the moments on stage,” said Maxwell on Instagram. “But I’ve been fortunate enough to see the moments behind the curtain that truly define what makes a star, a star.”

 

32. Kerry Washington

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“Kerry likes to balance femininity with edge,” says Washington’s stylist Joseph Cassell, citing the star’s Tory Burch Met Gala gown as one of her most avant-garde looks. “She isn’t afraid to take a risk.”

 

33. Rowan Blanchard

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When Blanchard (in Marc Jacobs) isn’t killing it on the step and repeat, she’s the queen of the high-fashion selfie, thrilling her 5.1 million followers with every creative #LOTD. As for the feedback? “I really like how I dress,” she says, “So if somebody says something [rude], I don’t care.”

 

34. Sienna Miller

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In Louis Vuitton at the brand's fall show in Paris.

 

35. Patricia Clarkson

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In Michael Kors Collection at the InStyle Badass Woman Dinner in L.A.

 

36. Hunter Schafer

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In Thom Browne at the Build Speaker Series in N.Y.C.

 

37. Margot Robbie

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Throughout her entire Once Upon a Time in Hollywood press tour, Robbie’s ethereal gowns (including this Chanel Haute Couture number) and smoldering beauty looks stole the show. Movie-star glam at its finest.

 

38. Lena Waithe

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“This is what a CEO looks like now," says Waithe (in Pyer Moss, right). "I’m not always in a suit, but I always want to look cool and be comfortable."

 

39. Allison Janney

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Dramatic silhouettes, sophisticated color palettes, and a whole lot of bling — over the years Janney (in Alberta Ferretti) has found a red-carpet strategy that only gets better with time. “I call it classic with a flair for the theatrical,” she says.

 

40. Gwendoline Christie

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In Iris van Herpen at the Game of Thrones premiere in N.Y.C.

 

41. Michelle Dockery

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At the London premiere of the long-awaited Downton Abbey movie, Dockery delivered one sexy return to the red carpet in this gilded Galvan creation, Cartier hoops, and a slicked-back do. Lady Mary would certainly be proud.

 

42. Yalitza Aparicio

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In The Vampire’s Wife at Vanity Fair's New Hollywood party in L.A.

 

43. Rihanna

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In Alexandre Vauthier Couture at the Savage x Fenty show in N.Y.C.

 

44. Gwyneth Paltrow

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In G. Label by Goop at the Avengers: Endgame premiere in L.A.

 

45. Zendaya

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Besides earning her street-style cred and a prime spot in the New York Fashion Week lineup (her second collection with Tommy Hilfiger launched this fall), Zendaya’s statement-making looks have helped her overcome personal obstacles as well. “I allow fashion to be an outlet and a way to experience different sides of who I am,” says the star (in David Koma). “It’s given me a lot of confidence.”

 

46. Sophie Turner

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In Louis Vuitton at the Deauville American Film Festival in Deauville, France.

 

47. Michelle Yeoh

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In an Elie Saab dress at the Charles Finch and Chanel pre-Oscar dinner in L.A.

 

48. Millie Bobby Brown

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In a Maje jacket in London.

 

49. Taraji P. Henson

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“My favorite fashion moment this year was at the BET Awards," she says. "I changed three times and then instantly fell in love with my spiked Balmain dress.”

 

50. Judith Light

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“When I get dressed, I think, ‘Who do I want to be in this moment?’” says Light (in Christian Siriano). “The answer is usually someone bold and elegant.”

For more stories like this, pick up the November issue of InStyle, available on newsstands, on Amazon, and for digital download Oct. 18.