Flashback: Grammy Awards Red Carpet Hits & Misses Ranked

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35. Hit: Bebe Rexha – 2018

Bebe Rexha stepped out looking sleek and chic at the 2018 Grammy Awards! Her look consisted of a curve-hugging dress in a blush pink color that was the perfect balance of soft and sexy. We love the contrast of the bronze tulle along the bust and the gold glitter beaded throughout the gown. This subtle glittering look flattered her skin tone and made her platinum blonde locks truly pop!

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34. Miss: Madonna — 2015

Madonna shocked everyone when she stepped out at the 2015 Grammys wearing this revealing black and pink ensemble. While we’ve come to expect bold fashion from the queen of Pop, we also wish she had opted for something a little more tasteful. The look showed an excessive amount of skin and had way too much going on to be a reasonable red carpet look.

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33. Hit: Lady Gaga – 2019

Lady Gaga blew us away with her silver ruffle dress at the 2019 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.

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32. Miss: Katie Holmes — 2018

Of all the red carpet fashion from the 2018 Grammy Awards, we were definitely the most disappointed with Katie Holmes’ look! Holmes stepped out wearing an ankle-length dress made of an awkward leather material that was quite unexpected. In combination with her dress, her vintage style waves and dark smokey eye seemed to age her rather than flatter her. We would have much preferred to see Holmes in something a little softer and more glam!

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31. Hit: Nelly Furtado — 2002

Nelly Furtado was the queen of the Pop music world back in the early 2000s when her hit song “I’m Like A Bird” was on every radio station. For the 2002 Grammys, the star opted for a seriously stunning Giorgio Armani dress that featured a nude underlay and a dainty, sheer floral design. The striking gown made for a delicate and eye-catching red carpet moment.

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30. Miss: Alicia Keys — 2004

Alicia Keys is an absolute beauty, which is why her 2004 Grammys look was such a disappointment! She could seemingly pull off anything with her glowing complexion and shiny locks, but this confusing outfit did her no justice. The look consisted of a pair of dark wash jeans and a color-blocked top which doubled as a dress and fanned out into a train behind her. To make matters worse, Keys rocked a denim cuff on one arm. The look was overall just quite casual for a formal awards show and will definitely go down as one of the most disappointing Grammys looks of all time.

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29. Hit: Katy Perry — 2009

Katy Perry’s style has shifted significantly throughout the years and we rarely have any idea what to expect when she steps out onto a red carpet. In 2009, however, she opted for a relatively tame route in comparison to some of her more theatrical looks. Perry opted for a blush pink chiffon gown that featured a dramatic satin bow detail along the front. The look was elegant, feminine and totally memorable!

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28. Miss: Katy Perry — 2017

Katy Perry’s 2017 Grammys dress was a definite red carpet miss! We’re quite accustomed to Perry’s out-of-the-box style and statement looks by now, but this dress was simply unflattering. The shiny fabric of the bodice came across as cheap-looking, especially because it clung to her body in all the wrong places. We also would have much preferred if the feathers formed a flattering mermaid shape of some sort rather than this column style shape which cut her awkwardly below the hips.

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27. Hit: Kim Kardashian — 2011

No one does a sultry gold dress better than Kim Kardashian! For the 2011 Grammys, the star opted for a draped golden dress that showed skin in all the right places without being over the top. It was sultry, seductive and most of all, totally glamorous.

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26. Miss: Alessia Cara — 2018

Alessia Cara is an absolute sweetheart, but this Canadian native unfortunately needs some assistance in the fashion department, especially after seeing her look for the 2018 Grammys. Her red carpet looks are notorious for being overly casual and she has made a habit of rocking t-shirts and sneakers as her awards show go-to. Although she didn’t land herself on the best-dressed list in 2018, she did go home with a Grammy Award in hand, so that’s quite the accomplishment in our books!

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25. Hit: Taylor Swift — 2012

The 2012 Grammys was a big night for Taylor Swift who snagged two awards for her hit song “Mean.” For the monumental evening, Swift opted for a full-glam golden dress by Zuhair Murad that featured a dramatic mesh cutout and intricate beading throughout. Rather than her typical head of curls, Swift opted for a sleek updo that was clean and sophisticated.

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24. Miss: Sheryl Crow — 2002

Sheryl Crow’s look from the 2002 Grammy Awards completely baffled us! She donned what appeared to be a black romper that laced up the front, which she paired with a floor-length grey fur coat. To make matters worse, Crow rocked a pair of cowboy boots that matched with the details of her romper and a pair of lightly tinted sunglasses. In her defense, sunglasses like this were definitely a trend at the time, but we were quite disappointed she took the risk of wearing them on the Grammy’s red carpet!

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23. Hit: Jennifer Lopez — 2017

One of the most memorable J.Lo looks of all time is this dreamy lilac Ralph & Russo dress that she wore for the 2017 Grammy Awards. While we often aren’t fans of oversized embellishment, since the rest of the dress is so simple the tulle detail on the shoulder looked super elegant.

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22. Miss: Lil Kim — 2002

Lil Kim most definitely made an entrance when she stepped onto the 2002 Grammys red carpet! Her red leather outfit consisted of a pair of skin-tight pants, a lace cropped top and a matching leather jacket. For accessories, Lil Kim chose a pair of oversized red sunglasses, a Chanel embossed motorcycle helmet, biking gloves, and an embellished belt. This look will forever go down as the most confusing Grammy looks we’ve ever seen.

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21. Hit: Chrissy Teigen — 2016

Chrissy Teigen has proved over the years that she has the chicest maternity style in all of Hollywood! She loves to show off her bump in chic dresses, and our ultimate favorite of hers is this sophisticated and glitzy white number she wore to the 2016 Grammys. The crystal cape was to die for and a fashion moment we’ll never forget.

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20. Miss: Halsey — 2017

In 2017, pajama-inspired clothing was definitely all the rage, but unfortunately, it appears that Halsey might have taken the trend a little too seriously at the Grammy Awards! Instead of a typical dress, Halsey opted for a matching silk tracksuit-inspired outfit that she left undone to expose a silver body chain. There is definitely a tasteful way to style the pajama trend, as we’ve seen many other stars do, but Halsey totally missed the mark with this royal blue ensemble.

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19. Hit: Rita Ora — 2018

Rita Ora mastered the little black dress when she stepped out at the 2018 Grammys wearing this sultry number designed by Ralph & Russo. What we especially love about this dress is the crystal detailing on the underside of the hemlines. It’s a subtle pop of glitz that’s unique and unexpected!

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18. Miss: Pink — 2003

Pink has always had a no-fuss attitude when it comes to fashion and award shows, but this particular 2003 Grammys look was quite extreme! The look consisted of a revealing floral halter top and a black sheer skirt with strange string detailing that seemed to hang in all the wrong places. She rocked a super dramatic cat eye and coiffed her hair into a rocker style updo. As much as we appreciate personal style and Pink’s classic hardcore attitude, we couldn’t help but feel a little disappointed with this look!

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17. Hit: Taylor Swift — 2016

Taylor Swift stole the show when she opted for this bold two-piece set by Atelier Versace at the 2016 Grammy Awards. Initially, a shade of coral mixed with fuschia wouldn’t seem to be the most natural pair, but Swift found a way to make it work flawlessly. The look was dramatic and seductive by showing a little skin, which marked a huge shift in Swift’s career from that of an innocent young country star to a full-blown glamorous pop star.

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16. Miss: Katy Perry — 2011

Katy Perry is so gorgeous that she can really pull off almost any look, but unfortunately she really missed the marks at the Grammy Awards in 2011. It kind of seems Perry got the Grammy’s mixed up with the Victoria’s Secret fashion show, donning a long, sheer white skirt complete with full white wings. A good look for other events, or Halloween, but definitely not the Grammys!

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15. Hit: Kelly Rowland — 2013

Cutouts are a tricky look to pull off when it comes to the red carpet and there is a fine line between coming across as tasteful or tacky. The jaw-dropping Georges Chakra gown that Kelly Rowland wore at the 2013 Grammy Awards was definitely one of the riskiest cutout dresses we’ve seen and featured strategically placed geometric sheer designs throughout. The risque gown was undeniably a talking point at the 2013 Grammy Awards, especially after CBS sent a memo advising celebrities to avoid sheer, see-through clothing. “It’s so funny! I thought about the dress code and thought about it again, and that’s about it,” Rowland joked at the time.

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14. Miss: Heidi Klum — 2018

Heidi Klum definitely had a peak in her red carpet style these past few years; however, it seems that at the 2018 Grammys she missed the mark. This sheer, black gown featured far too many cutouts and textures that it came across tacky and confusing. We can definitely appreciate the sultry quality of a cutout, jet black gown, but Klum’s look from the Grammy red carpet showed a little too much skin to pull the look off tastefully.

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13. Hit: Katy Perry — 2012

Katy Perry is the ultimate fashion chameleon and has transitioned her sense of style more than a few times throughout her career. Her 2012 Grammys look was one of our ultimate favorites and definitely a peak in Perry’s fashion evolution! The powder blue Ellie Saab dress was completely covered in soft, sheer applique that was feminine yet still sultry. The choice of dress couldn’t have been better with her electric blue hair color at the time and her luminous makeup and pink lip definitely added a softness to the look.

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12. Miss: Lady Gaga — 2010

Music icon Lady Gaga definitely dresses for the shock factor instead of the style factor. Over the years fans have seen the star in quite a few bizarre ensembles and the Grammys in 2010 were no different. From the hair to the shoes to the dress itself, there was definitely a lot going on with this look, and it’s still not clear how she sat down, or if she was even able to!

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11. Hit: Kim Kardashian — 2015

Kim Kardashian’s Grammy Awards dress from 2015 was definitely one of her most memorable looks ever. The 100 lb Jean Paul Gaultier gown featured embellished shoulders, a plunging neckline, and a glittering waist-cinching crystal belt. The intricate, glittering gown looked like a piece of art straight off the cover of Vogue and definitely made this Kardashian look like a glamour queen at the 2015 Grammy Awards!

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10. Miss: Rihanna — 2008

Over the years Rihanna has changed her style both personally and musically. She has become quite the fashion icon, but she has admittedly hit a few snags over the years as well. The gorgeous singer did not dress to impress when she attended the Grammys in 2008. Her cobalt dress had a lot going on at once from the fringe to the ruffles and we’re not sure it came together as a winning style moment.

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9. Hit: Carrie Underwood — 2012

Carrie Underwood’s head to toe sequined gown from the 2012 Grammy Awards was one of the highlights of the evening. The show-stopping gown was sleek and sharp, but still intricately designed and luxurious! The simple gown featured a cutout along the back which Carrie allowed to shine by pulling her hair into an elegant and loosely coiffed updo.

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8. Miss: Cyndi Lauper — 2008

Cyndi Lauper is amazing, but more than once her Grammys fashion has been a bit questionable. We have to excuse her for her 1984 Grammys look because ’80s fashion was innately quite bold, but in 2008 she still didn’t seem to have a handle on the best red carpet styles for the event. From the gloves to the lace to her bold hair, this definitely didn’t come together as a fashion win.

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7. Hit: Jennifer Lopez — 2011

Jennifer Lopez has never shied away from flaunting her amazing and toned figure, and while her 2000 Grammy Awards dress has gone down in history, her 2011 dress was also spectacular. J.Lo rocked a short and shimmering silver metallic Emilio Pucci dress. As if Lopez needed any help being eye-catching, this dress did the trick and was one of the most talked-about looks of the night.

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6. Miss: Jennifer Lopez — 2000

Year after year after year, Jennifer Lopez stuns and turns head on every red carpet she walks, and while she never seems to age and her body always looks good, her Grammy’s look in 2000 took things just a little too far. She seemingly wore a beach cover-up without the beach or a bikini for that matter. There’s definitely a fine line between looking sultry and revealing too much.

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5. Hit: Rihanna — 2013 

Over her years of attending the Grammys, Rihanna has had both hit and misses, but one of her most memorable looks was her 2013 Grammy Awards gown. The singer wore a custom-made Azzedine Alaia red dress which mastered the use of sheer cutouts way before they were popular. Rihanna herself said the dress was “stunning” and loved the vibrant look which she made sure to match to both her lips and her nails.

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4. Miss: Fergie — 2012

Fergie may be stunning but, unfortunately, the singer has landed on quite a few fashion miss lists over the years. The Grammys in 2012 was one of those times when she stepped out wearing this orange lace dress that was completely sheer. The dress bared all and left little to the imagination, which is why we admittedly weren’t the biggest fans.

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3. Hit: Beyonce — 2014

Beyonce has always stunned at the Grammys. From her days with Destiny’s Child to going solo, she has never failed to impress, and one of her best looks was at the Grammy Awards in 2014. Queen B wore a white and lace Michael Costello gown which received rave reviews and kept the buzz going for weeks afterward.

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2. Miss: Nicki Minaj — 2012 

Similar to Lady Gaga, Nicki Minaj intentionally aims to shock with some of her outfits she wears to awards shows. The pop star has a long list of questionable Grammy’s outfits including her 2011 leopard print suit and of course 2012’s red hooded ensemble which she wore while accompanied by an elderly man dressed as the Pope.

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1. Hit: Taylor Swift — 2015

2015 may seem like decades ago now to some, but at the time, high-low skirts and dresses were all the rage and when Taylor Swift showed up to the 2015 Grammys, she stunned everyone. Donning a shimmering blue Elie Saab gown, jaws-dropped when Swift took the red carpet, and it quickly became of the most memorable Grammy looks of all time.

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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.