Oscars 2019: All Of The Best & Worst After Party Looks Ranked

If you were impressed by the 2019 Oscars’ red carpet fashion this year, you’ll be blown away by some of the fabulous After Party looks. Each year, Vanity Fair hosts a star-studded Oscars’ After Party where celebrities slip into something a little more party-appropriate. We love the glitzy, swoon-worthy evening ensembles that celebrities step out in, but that doesn’t mean there aren’t also a few after party looks that fell flat. Follow along as we rank all the best and worst 2019 Oscars’ after party looks for this year’s Vanity Fair party:

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40. Worst: Serena Williams

Serena Williams wore a gorgeous black and red gown for the official Oscars red carpet that had all eyes on her, but we can’t say the same for her after party look. The blue and black look felt chaotic and the double layered tulle on the skirt was super distracting.

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39. Best: Kacey Musgraves

After wearing a disastrous pink tulle dress for the official red carpet, we let out a sigh of relief when we saw Kacey Musgraves step out at the Vanity Fair after party wearing this sleek bronze dress. It was the perfect party look with a glitzy texture, body-skimming shape, and flattering color.

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38. Worst: Letitia Wright

Letitia Wright stepped out wearing this rich yellow gown at the 2019 Oscar awards after party that initially we didn’t find too bad. The peach bows on the shoulders, however, seemed to really detract from the look. The color of the bows clashed and they distracted from the gorgeous print and texture of the dress itself.

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37. Best: Ciara

Ciara made jaws drop when she stepped out at this year’s Oscars’ after party wearing a sleek dress with silver and blush pink accents. We absolutely loved how unique this look was and how it almost looked like two different dresses from each side! It was elegant, glitzy and pure perfection.

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36. Worst: Behati Prinsloo

Behati Prinsloo stepped out at the 2019 Oscars’ after party wearing head to toe cheetah print. We are huge fans of animal print, but this simply felt like overdoing the trend. We wish Prinsloo had opted to wear cheetah in a more subtle, effortless way.

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35. Best: Chloe Grace Moretz

Chloe Grace Moretz stunned at the 2019 Vanity Fair party where she stepped out in this gunmetal silver dress that was the perfect balance of dainty and flashy. We absolutely love the sleek, body-skimming shape of this dress and how the deep silver color brings light to her blue eyes.

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34. Worst: Chloe Sevigny

Chloe Sevigny stepped out at the 2019 Vanity Fair party wearing a puzzling black ensemble that we, admittedly, didn’t love. From the ruffled shoulder to the large cutout, to the sequin skirt, there was far too much happening at once.

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33. Best: Miley Cyrus

Miley Cyrus has gone through quite a few phases when it comes to red carpet fashion, but we think 2019 might be her best year yet. She’s narrowed down her style to many classic pieces with a modern twist, like this sequined plunging dress. We love this elevated, party vision of a classic little black dress and how she jazzed it up with bold silver jewelry.

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32. Worst: Sophie Turner

Sophie Turner stepped out at the 2019 Oscars’ after party this year wearing a look that, unfortunately, missed the mark. We love a strong sequin dress for an after party, but this look featured unsightly ruffles that flared out at an unflattering height on her waist and really detracted from the dress as a whole.

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31. Best: Shay Mitchell

Shay Mitchell was an absolute knockout at the 2019 Vanity Fair party where she stepped out in this gorgeous deep green dress. We love the subtle feather detailing around the neckline and how glamorous the wispy sleeve detailing looked. This look was truly unique and unlike any red carpet dress we’ve seen before, which is why we were such big fans.

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30. Worst: Jessica Alba

Jessica Alba is one of the most beautiful women in Hollywood who could seemingly pull off anything. While the dress she wore to the Oscars’ after party wasn’t overly awful, it simply wasn’t a standout look like we were hoping to see. The black dress sat loosely on her body and didn’t particularly flatter her figure. Overall, we just felt the look was quite underwhelming which was disappointing.

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29. Best: Constance Wu

Crazy Rich Asians star Constance Wu dazzled on the Oscars’ red carpet in a floaty marigold dress, but she really brought the drama with her after party look! This pleated metallic number was super flattering and glamorous. We especially love the unique asymmetrical neckline that featured dark, sultry feathers trailing down her back.

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28. Worst: Olivia Colman

Olivia Colman may have won the Best Actress award at the 2019 Oscar Awards this year, but unfortunately, she didn’t win in the fashion department. The actress stepped out wearing a confusing green dress on the official red carpet and a similarly puzzling look to the after party. The satin texture of this dress came across as slightly cheap looking since it was a seemingly aged yellow color and wrinkled.

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27. Best: Alessandra Ambrosio

Supermodel Alessandra Ambrosio stepped out at the Vanity Fair after-party this year and instantly had all eyes on her. She donned a dreamy powder blue dress that featured a plunging neckline and high slit that was balanced out with a cape-style sleeve and dainty lace embroidery on the bodice.

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26. Worst: Chrissy Teigen

We absolutely love Chrissy Teigen’s chic sense of style, but we, unfortunately, weren’t the biggest fans of her Oscars’ after party look this year. The combination of the mesh texture of the dress with a floral print pattern and feather embellishment simply felt a little chaotic.

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25. Best: Laura Dern

Laura Dern had an unfortunate fashion miss on the official Oscars’ red carpet this year, but luckily she made up for it with her stunning after party look. We absolutely love this black beaded number! It was glitzy, sultry and the perfect black dress for an evening of celebrating.

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24. Worst: Taraji P. Henson

Taraji P. Henson sadly missed the mark with her Vanity Fair after party look this year. The major reason we didn’t enjoy this look is because of the texture of the dress, which photographed quite strange and was almost plastic-looking on camera.

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23. Best: Kerry Washington

Kerry Washington looked absolutely angelic at the Vanity Fair after-party this year where she stepped out in this nude corset-style dress. The look felt really delicate with the strapless neckline and sheer bodice, but also dramatic with the voluminous, tiered skirt.

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22. Worst: Tessa Thompson

We have to admit we weren’t the biggest fans of this black sheer dress worn by Tessa Thompson at the Oscars’ After Party this year. We didn’t love the chunky silver and black glitter on this dress, which made it appear a little cheap, especially when paired with the heavy black boots she opted for.

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21. Best: Amy Adams

Amy Adams absolutely nailed both her official Oscars’ look and her after party ensemble this year! This rich, jewel-tone blue dress looked so lovely on Adams. We love the plunging neckline, which showed a little skin without showing too much. The sparkling brooch and pleats along the skirt really brought the drama with this look.

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20. Worst: Natalie Portman

Natalie Portman has had quite a few memorable red carpet moments throughout Oscar history, which is why we always have high expectations when she hits the red carpet. Portman’s after party look this year was quite disappointing in all honestly! A plain black look like this could easily be worn for any other event and we wished she had opted for something a little more special on Oscars’ night.

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19. Best: Rosie Huntington-Whiteley

Supermodel Rosie Huntington-Whiteley absolutely dazzled at the Vanity Fair party this year where she stepped out wearing a head to toe silver gown. What we especially love about this sequin number is the asymmetrical neckline, which really made it stand out and look unique in a sea of sparkling after party gowns.

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18. Worst: Emilia Clarke

We swooned over Emilia Clarke’s sculptural lilac dress she wore on the Oscars’ red carpet this year, but we can’t say we felt the same for the little red dress she wore to the after party. The dress seemed to cut her at an awkward angle at the ankles which didn’t properly elongate and flatter her. This look also definitely could have skipped on the oversized puff sleeves.

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17. Best: Sarah Hyland

Sarah Hyland was a total showstopper at the Vanity Fair party this year where she stepped out wearing a magenta pink one-shoulder number that fit her like a glove. The sleek, body-skimming shape of this dress really flaunted Hyland’s petite figure and the touch of turquoise on her earrings was the perfect colorful punch of contrast to her dress.

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16. Worst: Rowan Blanchard

Rowan Blanchard stepped out at the 2019 Vanity Fair party wearing quite an interesting ensemble this year. From the enormous oversized shoulders to the embroidered flower print, this look simply had too much going on.

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15. Best: Winnie Harlow

Winnie Harlow mastered the art of rocking a dramatic dress at this year’s Vanity Fair party. We love how this look featured a high low cut which allowed Harlow to still show a little leg without getting lost in ruffles and tulle. This was such a flawless red carpet princess moment!

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14. Worst: Emily Ratajkowski

We were disappointed to see Emily Ratajkowski miss the mark with her Oscars’ after party look this year. The color of this dress did nothing for her complexion and the combination of lace and peplum felt a little mismatched.

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13. Best: Madelaine Petsch

Riverdale star Madelaine Petsch wore the most beautiful gown to the Vanity Fair party this year! This look felt so whimsical and feminine, but also bold with the full textured skirt. She topped the striking look by sleeking back her hair and adding a pop of deep red on her lips.

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12. Worst: Lily Collins

We were less than impressed with this look that Lily Collins opted for at the Oscars’ after party this year. The burgundy abstract print of this dress wasn’t the most flattering, especially when it transitioned to awkward looking tulle along the skirt.

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11. Best: Kiki Layne

Kiki Layne had two winning fashion moments at the 2019 Oscars this year. The first being the pale pink dress she wore on the red carpet, the second being this jaw-dropping metallic gown she wore to the Vanity Fair party. We absolutely love the contrast of the shiny silk texture with the sheer, beaded paneling.

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10. Worst: Naomi Campbell

Naomi Campbell opted for a long sleeve embellished gown for this year’s Vanity Fair party that we have to admit we didn’t love. The high neck, long sleeve dress felt a little stifling and none of the colors of the embroidery particularly popped out to flatter her skin tone.

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9. Best: Lupita Nyong’o

Lupita Nyong’o stole the show at the Oscars’ after party this year where she stepped out in a full feathered gown. When it comes to feathers, it’s important to style them strategically so the look doesn’t appear overwhelming, which Lupita Nyong’o nailed. By showing a little shoulder, leg and adding a belt, she still managed to show off her figure among all the glamorous and bold feathers. This is a head-turning party look we’ll never forget!

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8. Worst: Heidi Klum

Heidi Klum missed the mark on her Oscars’ after party look this year which was quite disappointing. The combination of the black feathers, heavy embellishment and a strange train made for a less than impressive ensemble.

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7. Best: Emma Roberts

It seems like Emma Roberts can do no wrong when it comes to awards show fashion! We absolutely love this delicate glitter dress she wore to the Vanity Fair after-party this year. It had such a soft, but still sultry feel to it with the draped tulle sleeves, high slit and sheer detailing.

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6. Worst: Halsey

Halsey had an unfortunate fashion miss at the Oscars’ after party this year where she stepped out in this bizarre embellished plaid dress. Plaid and embroidery should never go together and this look is definitely proof of that.

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5. Best: Kate Bosworth

Kate Bosworth absolutely stunned at the Vanity Fair party this year in this delicate yellow gown that was totally unique. We love the flattering ruched detailing along her neck and how flawlessly this elegant number skims her figure.

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4. Worst: Maya Rudolph

Maya Rudolph had two pink fashion misses this year at the Oscars. First on the official red carpet, and then at the after party. This asymmetrical magenta party look seemed to add unnecessary volume to her figure and didn’t feel properly tailored to flatter.

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3. Best: Jennifer Lopez

Jennifer Lopez was a red carpet all-star at this year’s Oscars! She absolutely nailed her official red carpet number in a mirrored silver dress and then brought even more fabulousness to the Vanity Fair party afterward. This sparkly indigo number is unlike anything we’ve ever seen before. We absolutely love the ombre, fanned out embellishment on the bodice.

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2. Worst: Kendall Jenner

Kendall Jenner wore one of the most uncomfortable looks we’ve ever seen her in at this year’s Vanity Fair party. This look was without a doubt a fashion catastrophe and wardrobe malfunction waiting to happen.

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1. Best: Gemma Chan

Of all the looks at this year’s Vanity Fair party, we have to give major kudos to Gemma Chan with this sparkling fringe number she donned. It was the epitome of a fabulous party look with a little glitz and glamour, but totally unique and unlike any other look at the event with the swoon-worthy fringe. It’s iconic to say the least!

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