Grammy Awards 2019: 20 Most Disappointing Looks

The annual Grammy Awards always features much more experimental fashion than the typical awards show. It’s the perfect opportunity for celebrities to take a risk with their fashion, but sometimes it’s not a risk well rewarded and leaves their fans somewhat disappointed. Follow along as we recap all the looks for the 2019 Grammy Awards that we had high expectations for but ended up falling flat:

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20. Hennessy Carolina

Cardi B’s sister Hennessy Carolina seems to be following in her sister’s footsteps with her bold fashion choices. This oversized orange ensemble Carolina wore to the 2019 Grammys definitely left us quite baffled. The dress felt like a fashion malfunction waiting to happen and the oversized sleeves were quite unnecessary.

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19. Jeannie Mai

We love the look of a crisp white jumpsuit on the red carpet, but we weren’t fans of this look worn by Jeannie Mai at the 2019 Grammys. 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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18. Andra Day

Andra Day stepped out at the 2019 Grammys this year wearing a bold, velvet purple dress with feather-embellished sleeves. We were disappointed with this look because feathers have been a huge trend in 2019, but since this trend is so bold, it’s key to style it in a subtle, understated way. Andra Day overdid it by combining feathers with such a bold color, which made the entire look come across quite tacky.

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17. 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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16. 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 which was a slight let down.

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15. Little Big Town

While it’s important to have an impressive fashion moment as an individual, if you’re a band it’s also important to consider how you will coordinate together on the red carpet. Unfortunately, this isn’t something that Little Big Town took into consideration, which is why we were disappointed. The group had so many unique approaches to red carpet fashion that as a band they looked disjointed.

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14. 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, which is why it was slightly disappointing.

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13. 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 were quite disappointed to see her on yet another worst-dressed list.

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12. 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 felt like an ’80s shoulder pad dress gone wrong. Based on previous awards shows, Heidi Klum seemingly has mastered the art of appropriately dramatic fashion, but this look simply overdid it, which left us disappointed.

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11. Dolly Parton

Dolly Parton is a Grammys icon, but we have to admit her choice of attire for this year’s Grammys wasn’t the most impressive. From the silver beading to the strange neckline, we definitely think Parton could have done better with this underwhelming red carpet look. We actually would have preferred if she had walked the red carpet wearing the white flowy dress she wore on-stage when she performed!

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10. Toni Braxton

While the Grammy Awards is definitely welcoming to untraditional fashion, that doesn’t mean that stars have to skip on modesty. We were quite disappointed with this overly revealing look worn by Toni Braxton at the Grammy Awards this year. The look bared it all, but uncomfortably so.

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9. Ella Mai

Ella Mai stepped out at the 2019 Grammy Awards wearing a dramatic navy dress that had very little shape to it. We simply felt that Mai drowned in the billowing shape of this dress and would have much preferred to see this look with some sort of a sash to balance it out. We also weren’t the biggest fans of this deep blue color since it blended in with the black backdrop and washed out the details of her look.

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8. Janelle Monae

Janelle Monae has established herself as a fashion icon in Hollywood and we can almost always expect her to step out in something totally unpredictable and bold. While her Grammys look was obviously quite dramatic, we, unfortunately, weren’t the biggest fans. This sculptural look simply felt too bold for the event and better suited for the Met Gala.

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7. Alessia Cara

Alessia Cara is an emerging artist to watch, but from the look of her outfit, you wouldn’t think so! She opted for something quite subdued and simple that left no real impression on us. We wish the stunning singer opted for something less dull and perhaps with a little glitz and glamour to make her stand out as the talented musician she is.

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6. Rashida Jones

Rashida Jones was another starlet whose look felt quite underwhelming on the Grammys red carpet. Her deep navy dress blended into the black backdrop of the Grammys red carpet and had no real quality about it that made it stand out. For someone up for a Grammy nomination, and who ultimately won, we expected more for her red carpet look!

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5. 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 beautiful gown, which was quite disappointing.

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4. 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! This was totally disappointing because the night was so epic for her and we would have loved to see her beautiful face.

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3. 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 her look. It’s always a shame when one unsolicited detail throws off an entire look!

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2. Ariana Grande

After a controversy with the Grammys producers about what song she would perform at the event this year, Ariana Grande made the tough decision to skip out on the Grammys. Since she had intended to attend, she already had a Zac Posen custom gown ready to go for the red carpet. The dress was absolutely jaw-dropping, which is why we were so disappointed we didn’t get to see Grande wear it on the red carpet.

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1. Kylie Jenner

Of all the looks at this year’s Grammy Awards, we were the most confused and disappointed with this Balmain look worn by Kylie Jenner. It totally drowned her shape in every way from the bizarre sleeves to the oversized pants. For a star with so much natural style, this look definitely missed the mark and left her fans disappointed.