Home » Style » Fashion » Grammy Awards: Disappointing Red Carpet Looks Of Year’s Past

Grammy Awards: Disappointing Red Carpet Looks Of Year’s Past

Olivia Di Pede

February 4, 2019

Photo By: Elizabeth Goodenough/Everett Collection

Grammy Awards: 7 Best Dressed From Years Past

The annual Grammy Awards is undeniably one of the most anticipated nights in the entertainment and music industry. Hollywood stars from all facets come together to celebrate the best in music, while bands, singers, and writers from all different genres hope for one of the prestigious awards. Although the night might be focused on music and achievement, it is also one of Hollywood’s biggest nights for red carpet style. All eyes will be on the stars walking the red carpet, and over the years there have been many memorable gowns, but unfortunately, quite a few disappointing ones as well. Check out the times we expected more from a few of our leading red carpet fashionistas and ended up disappointed:

18. Fergie — 2004

Back when Fergie was a member of the Black Eyed Peas, she stepped out at the 2004 Grammys wearing this revealing white fringe number. The look was quite disappointing because of how little fabric there was and how the fringe came across slightly tacky. We love how Fergie’s style has progressed over the years and she’s shifted towards a more sophisticated, yet still sultry, sense of fashion.

13 Popular Artists Who Have Never Won A Grammy!

17. 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.

Photo By: Charlie Williams/Everett Collection

Met Gala 2022: Red Carpet Hits & Misses

16. 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!

Photo by Lionel Hahn/ABACAPRESS.COM

2022 ACM Awards: Red Carpet Hits & Misses Ranked

15. 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 seriously 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.

Photo by: Hahn-Khayat/ABACA

SAG Awards 2022: Red Carpet Hits & Misses Ranked

14. 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 cheap looking, especially because it clung to her body in all the wrong places. We also would have much preferred if the feathers flourished into a flattering mermaid skirt of some sort rather than this voluminous column style shape which cut her awkwardly below the hips.

Photo by Broadimage/REX/Shutterstock

Met Gala 2021: Red Carpet Hits & Misses

13. 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!

Photo by Charles Sykes/Invision/AP

Emmys 2021: Red Carpet Hits & Misses

12. 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!

Source: Shutterstock

2021 ACM Awards: Red Carpet Fashion Hits & Misses Ranked

11. 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’s look we’ve ever seen.

Source: Shutterstock

Oscars 2021: Red Carpet Hits And Misses Ranked

10. 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.

Photo by Jim Smeal/BEI/Shutterstock

Golden Globes 2021: Red Carpet Fashion Hits & Misses Ranked

9. 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! There is definitely a way to still look polished and appropriate for an event while still staying true to your style, and unfortunately, Pink just didn’t quite achieve that.

Source: Shutterstock

Grammy Awards 2021: Red Carpet Fashion Hits & Misses Ranked

8. 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 Grammy’s!

Photo by Broadimage / Rex Features

Kate Middleton's Fashion Hits & Misses Of 2020

7. 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 sex appeal 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.

Photo by Lionel Hahn/ABACAPRESS.COM

Ranked: The Royal Family's Fashion Hits & Misses Of 2020

6. Lady Gaga — 2010

It seems almost pointless to put Lady Gaga on this list as she purposefully dresses for the shock factor instead of the style factor. Over the years fans have seen a lot of weird outfits on the singer and the Grammys in 2010 were no different. From the hair to the shoes to the dress itself there is nothing right about this outfit, and it’s still not clear how she sat down…or if she was able to.

Photo by BDG / Rex Features

American Music Awards 2020: Red Carpets Hits And Misses Ranked

5. Rihanna — 2008

Over the years Rihanna has changed her style both personally and musically, and as such as become somewhat of a fashion icon, but she has hit some snags over the years. The always gorgeous singer did not dress to impress when she attended the Grammy’s in 2008; her dress had a lot of different things going on with it from the fringe to the ruffles, and in the end, it looked like a bad ’80s prom dress.

Photo by Lionel Hahn/AbacaUsa.com

ACM Awards 2020: Every Red Carpet Look Ranked

4. 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 weird for everyone, but in 2008 she still didn’t seem to have a handle on the best red carpet styles for the event. The dress wasn’t flattering and was awkward, plus Cyndi just looked completely out of it.

Photo by Lionel Hahn/AbacaUsa.com

MTV VMAs 2020: Red Carpet Looks Ranked

3. 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 bikini for that matter. There’s being sexy and then there is letting it all hang out which she certainly did on music’s biggest night.

Featureflash / Shutterstock.com

Every Outfit Kate Middleton Wore On The Royal Ireland Tour

2. Fergie — 2012

Fergie may be stunning but, unfortunately, the singer has landed on the worst dressed list at various Grammy shows over the years. She just can’t seem to master the best fashion for these big events including the Grammy Awards in 2012 where she donned the sheer dress look before it became massively popular. The look isn’t flattering on pretty well anybody, but the intense color of hers made it even worse.

Photo By: Elizabeth Goodenough/Everett Collection

Kate Middleton's Fashion Hits & Misses Of 2019

1. Nicki Minaj — 2012

Again, like Lady Gaga, Nicki Minaj has to intentionally be aiming to shock with some of her outfits because there is no way someone could wear what she has worn to many different Grammy shows over the years and think it looks good. Year in and year out Nicki has worn questionable Grammy’s outfits including her 2011 leopard print suit and of course 2012’s red hooded ensemble which she wore while attended by an elderly man dressed as the Pope.

Photo By: Elizabeth Goodenough/Everett Collection

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.