Grammy Awards 2019: All Of The Best & Worst Dressed Stars Ranked

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29. Worst: St. Vincent

Singer St. Vincent is always untraditional when it comes to her red carpet fashion and the 2019 Grammy Awards was no exception. She stepped out wearing a black and white dress that featured oversized sleeves and a bold iridescent pattern. As much as we love St. Vincent’s ability to look outside the box, we have to admit we weren’t the biggest fans of this look.

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28. Best: Alicia Keys

Alicia Keys was the host of last night’s Grammy Awards and stepped out wearing a few different looks over the course of the evening. The most notable, however, was the long sleeve red dress she wore on the red carpet. The look was sleek and eye-catching with its plunging neckline, dainty buttons, and vibrant cherry red color.

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27. Worst: Brandi Carlile

We love seeing a strong suit on the red carpet, but we have to admit we didn’t love this specific suit look worn by Brandi Carlile. We didn’t mind the embellishment on the jacket, but the length of this suit jacket seemed to drown her, especially in combination with the bow tie and stifling button-up shirt.

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26. Best: Tracee Ellis Ross

Tracee Ellis Ross dazzled in this green suit look at the 2019 Grammys this year. Her look was the perfect example of being experimental, but not over the top. It was undeniably bold, especially with the snake-detailed belt, but that’s exactly why it grabbed attention for all the right reasons.

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25. Worst: Saint Heart

Saint Heart stepped out at the 2019 Grammys wearing a butterfly-inspired dress that had fashion critics everywhere scratching their heads. The look featured actual wings which she showed off proudly for photos on the red carpet. We, unfortunately, found this butterfly look quite tacky rather than experimental in the name of fashion.

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24. Best: Meghan Trainor

Meghan Trainor stepped out wearing a sleek white jumpsuit that looked absolutely gorgeous on her for the 2019 Grammy Awards. From the plunging neckline to the strong shoulders to the subtle glitter detail, this was the epitome of a winning Grammys look.

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23. Worst: Jeannie Mai

While Meghan Trainor nailed the white jumpsuit look, Jeannie Mai, unfortunately, did not. We were quite confused by the nude cutouts on her jumpsuit and felt that it wasn’t the most flattering option for the American television personality.

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22. Best: Kelsea Ballerini

Kelsea Ballerini dazzled on the Grammys red carpet where she stepped out wearing this delicate champagne-colored dress by Jenny Packham. We love the subtle beading and glitter on the dress and it was nice to see a classy, elegant number in the midst of so many bold Grammys looks.

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21. Worst: Cardi B

Cardi B had a five-person entourage help carry her dramatic Grammys look onto the red carpet this year. The look was inspired by a pearl-and-oyster clam which featured an upturned pink satin skirt and shimmering nude bodysuit. She topped the look with gloves and pearls around her neck and in her hair. While this look was undeniably deserving of applause, we simply think it was better suited for the Met Gala than the Grammys.

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20. Best: Jada Pinkett Smith

Jada Pinkett Smith absolutely dazzled on the Grammys red carpet this year where she stepped out in metallics and feathers in the most tasteful way possible. Her look was the perfect example of being dramatic and glitzy without going over the top.

(Photo by Jordan Strauss/Invision/AP)

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19. Worst: Little Big Town

Little Big Town stepped out at the Grammys this year wearing a strange combination of diverse looks. We really appreciate when bands attempt to coordinate their looks so posing together on the red carpet flows and feels natural, but this wasn’t something Little Big Town considered. The group had so many unique approaches to red carpet fashion that as a band they looked disjointed.

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18. Best: Anna Kendrick

We rarely appreciate a mini dress for a formal awards show, but Anna Kendrick was a definite exception! We absolutely love this cutesy feather dress she donned at the 2019 Grammys. It was on-trend, bold and totaly glamorous.

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17. Worst: Ashanti

Ashanti stepped out at the 2019 Grammys wearing this heavy black and gold dress that we weren’t the biggest fans of. The combination of the black velvet and billowing skirt felt somewhat costume-like.

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16. Best: Ashlee Simpson

Ashlee Simpson stepped out at the 2019 Grammy Awards wearing this gorgeous silver jumpsuit. Feathers are a huge trend this year, but it’s also a trend that can easily go wrong if not styled properly. This, fortunately, wasn’t the case with Simpson’s look! The feathers were subtle and added red-carpet worthy drama to her ensemble.

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15. Worst: Nina Parker

Nina Parker stepped out at the 2019 Grammys this year drowning in pink ruffles. There was no shape or logic to this look, which is why we couldn’t get on board with it. Parker also topped her look with colorful converse sneakers that made the entire fashion situation even worse.

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14. Best: Katy Perry

Of all the experimental fashion looks of this years Grammys, we have to admit our favorite was Katy Perry’s bubblegum pink cupcake dress. A look like this definitely isn’t everyone’s cup of tea, but we think Perry pulled it off flawlessly. Few people could look this gorgeous in such a bold dress!

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13. Worst: Dolly Parton

Dolly Parton is a Grammys icon, but we have to admit her choice of attire for this year’s red carpet wasn’t the finest. From the silver beading to the strange neckline, we definitely think Parton could have done better with her red carpet look.

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12. Best: Miley Cyrus

Miley Cyrus showed a sleek and sophisticated side on the Grammys red carpet this year but also proved she hasn’t totally let go of her playfulness by posing with her tongue out. The look featured an oversized suit jacket that remained sultry and feminine with a plunging neckline that showed a little skin.

(Photo by Jordan Strauss/Invision/AP)

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11. Worst: Heidi Klum

Heidi Klum stepped out at this year’s Grammy Awards wearing an oversized white dress that featured sculptural wing-like details on the shoulders. While this look was obviously intended to be dramatic, we just felt it was a little much and turned heads for all the wrong reasons.

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10. Best: Camila Cabello

Camila Cabello looked absolutely radiant at the Grammy Awards this year where she stepped out wearing a fuschia pink glittering gown that featured a high-neckline and cutout along the back. Her look felt like everything a Grammys dress should be — glitzy, eye-catching and flattering.

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9. Worst: H.E.R.

While the deep indigo dress that H.E.R. wore on the Grammys red carpet this year wasn’t the worst, we couldn’t get over the fact that she decided to wear sunglasses for the entire event. Even when she went to accept her award on stage she kept them on!

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8. Best: Bebe Rexha

Bebe Rexha clapped back at the fashion designers who told her team she was “too big” to fit into their dresses by looking absolutely stunning at the 2019 Grammys Awards! She opted for a dress designed by Monsoori which was a striking shade of deep berry red. The look featured dramatic tulle tiers that created an epic red carpet Princess moment.

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7. Worst: Maren Morris

Country star Maren Morris stepped out at this year’s Grammy awards wearing a gown designed by Galia Lahav. While we actually don’t mind this muted dusty purple gown, the shoulder detail of the lime green embellishment totally clashed and detracted from the dress.

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6. Best: Dua Lipa

Dua Lipa stunned on the Grammys red carpet wearing this sleek metallic dress that made heads turn for all the right reasons. We absolutely love all the intricate criss-cross detailing on the bodice of this dress, especially in combination with the dramatic train which brought even more glamour.

(Photo by Jordan Strauss/Invision/AP)

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5. Worst: Jennifer Lopez

Jennifer Lopez was a total bombshell when she performed on stage at last night’s Grammy awards, but we have to admit we weren’t the biggest fans of her first red carpet look. While the dress itself wasn’t too bad, we can’t say the same for the wide-brim hat she decided to add to her look. It simply felt like it distracted from the detailing of her gown!

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4. Best: Kasey Musgraves

Kasey Musgraves was one of the most elegant stars at last night’s Grammy Awards where she stepped out in this muted tulle dress with a red sash. It felt feminine, floaty and dainty, which made it stand out from a lot of the more dramatic looks at the event.

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3. Worst: Janelle Monae

Janelle Monae is a total fashion icon, but we weren’t convinced by her look for this year’s Grammy awards. While we understand the Grammys is definitely more liberal when it comes to fashion, this sculptural look simply felt too bold for the event and better suited for the Met Gala.

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2. Best: Lady Gaga

Lady Gaga blew us away with her silver ruffle dress at last night’s Grammy Awards! This look actually seemed somewhat modest for how Gaga usually dresses for awards shows, which felt refreshing. It was obviously still dramatic but in a glamorous and appropriate way.

(Photo by Jordan Strauss/Invision/AP)

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1. Worst: Kylie Jenner

Of all the looks at this year’s Grammy Awards, we were the most confused with this Balmain look worn by Kylie Jenner. It totally drowned her shape in every way from the bizarre sleeves to the oversized pants.

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Olivia Di Pede

Olivia loves all things fashion, beauty, and entertainment. In her free time, she can be found taking yoga classes, reading thriller novels, and styling outfits on Instagram.