These Are The Most Iconic VMA Looks Of All Time, Including Britney With A Snake

Our opinion? Sure. But we dare you to disagree with us...

Britney Spears performing at the VMAs with a snake around her neck

by Lillian Sesiguzel |
Updated on

The MTV Video Music Awards are fast approaching, and we've decided to take a stroll down red-carpet-memory-lane. We've got everything covered, from the most bare of barely-there dresses to double denim ensembles to make even Canada weep. Please note, feelings of nostalgia are perfectly normal.

Historically, an awards ceremony is a classy affair filled with glitz, glamour and A-list celebs on their best behaviour. The VMAs, however, manages to create some of the most talked-about moments of any given year, thanks to some outlandish outfits and questionable speech-making (here's looking at you, Kanye). Is there anything more iconic than the Britney and Madonna kiss, after all? And don't even get us started on Lady Gaga's meat dress.

Ahead of this weekend’s 2019 awards, run with us on a trip down memory lane and examine the 20 most iconic outfits, as chosen by us. And don't worry Taylor, we'll let you finish.


The 20 Most Iconic VMA Looks Of All Time

Rose McGowan wearing a dress to the VMAs red carpet1 of 20

Rose McGowan, 1998

Who could forget the time in 1998 when Rose McGowan truly gave new meaning to the term 'naked dress'? An iconic VMA moment.

Cardi B at the 2018 VMAS in a purple off the shoulder dress2 of 20

Cardi B, 2018

In her first public appearance since the birth of her daughter, Kulture, Cardi B took a rather demure approach to the 2018 VMA's and we're into it. The singer sported a then-new pixie crop to compliment her Nicholas Jebran dress with a thigh high split to envy Angelina.

Cindy Crawford wearing a dress to the VMAs red carpet3 of 20

Cindy Crawford, 1992

Arguably our favorite super of all, it's Cindy Crawford, wearing a classic Versace creation by Gianni himself. This bondage inspired dress was made complete with Cindy's addition of the red ribbon, supporting the fight against HIV/AIDS.

Lady Gaga meet dress on the VMA red carpet4 of 20

Lady Gaga, 2010

When Lady Gaga wore a dress made of meat to the VMAs we were all shocked and maybe also initially confused. This statement echoed a speech that Gaga made called The Prime Rib of America, where she spoke of her wish to end discrimination of gay men and women serving in the US military.

Miley Cyrus at the VMAs5 of 20

Miley Cyrus, 2015

After the singles 'We Can't Stop' and 'Wrecking Ball' came this, a questionable silver surfer/spacewoman look from Miley. Nobody but Miley could pull this off. And that's all we have to say on the matter.

Naomi Campbell in a mint green velvet dress6 of 20

Naomi Campbell, 2016

Proof that you don't necessarily need to use shock tactics to make an entrance, the endlessly flawless Naomi stole the show in 2016 in this mint green Brandon Maxwell mini. We bow down.

Rita Ora on the red carpet at the VMAs7 of 20

Rita Ora, 2014

This backless satin number was a red carpet winner for Rita Ora. Designed by Donna Karan, complete with train and thigh-high slit, with the possibility of inspo from Jessica Rabbit. One gust of wind though...

Mariah Carey on the red carpet at the VMA8 of 20

Mariah Carey, 1997

No wonder her legs were insured. Red carpets need more Mariah, if you ask us.

Katy Perry in double denim on the red carpet at the VMAs9 of 20

Katy Perry, 2014

If there's anything better than Britney Spears and Justin Timberlake wearing matching denim ensembles to the 2001 American Music Awards, it's Katy Perry paying homage to that at the VMAs. Plus, it's custom Versace. Fancy.

Kendall and Kylie Jenner on the red carpet at the VMAs10 of 20

Kendall and Kylie Jenner, 2014

This was Kendall and Kylie's first time at the VMAs and, like any panicked party guest, they decided to play it safe and go with anything black.

Christina Aguilera on the red carpet at the VMAs11 of 20

Christina Aguilera, 2006

Remember when Christina Aguilera started channeling '50s glamour? Well, this is a prime example of that. Nice work, XTINA.

Beyonce and Daughter Blue Ivy attend VMAs in coordinating12 of 20

Beyoncé & Blue Ivy, 2016

Trust the Carter's to bring their A-game when it comes to matchy-matchy, mother-daughter moments. Beyoncé's date for the 2016 VMA's was her then four-year-old daughter, Blue Ivy. She wore a tiara, of course.

Madonna attends the VMAs in 1984 wearing lace13 of 20

Madonna, 1984

Perhaps one of her most iconic looks, Madonna attended the VMAs in 1984 sporting a belt reading 'BOY TOY' (obviously), complete with white lace gloves and her signature bustier.

Hailey Baldwin wears sequined jumpsuit at the 2016 VMA Awards14 of 20

Hailey Baldwin, 2016

Baldwin before the Bieber - at the 2016 VMA's Hailey stunned in a sultry sheer jumpsuit complete with barely there sandals and "I woke up like this" hair.

Pamela Anderson at the 1999 Vmas wearing a white corset and pink fluffy hat15 of 20

Pamela Anderson, 1999

Erm, we're sort of into it? Also, Kim Kardashian recreated this for Halloween. Who said fashion was circular?

Kim Kardashian red carpet sexy black dress16 of 20

Kim Kardashian, 2016

It wouldn't be a red carpet homage without a little Kardashian, and this 2016 look did not disappoint. Straying from her normal uniform of sleek tresses and strong contour, Kim took the 'less-is-more' approach to her beauty look to compliment her overtly sexy LBD. Is this possibly the most low-key the reality star has ever looked?

Kelly Clarkson on the red carpet at the VMAS17 of 20

Kelly Clarkson, 2005

Oh, Kelly Clarkson, you'll always have a place in our hearts. This golden gown was pretty chilled for the VMAs red carpet, and she just looks lovely. We're just off to listen to Breakaway...

Lil Kim wears a one shoulder purple jumpsuit and matching wig18 of 20

Lil Kim, 1999

The red carpet look that inspired a million fancy dress costumes (including Miley Cyrus in 2013) - is this one-shouldered, boob-baring jumpsuit the most famous of all VMA history?

Millie Bobby Brown wearing a ruffled Rodarte dress on the red carpet19 of 20

Millie Bobby Brown, 2017

The Stranger Thing's Actress made her red carpet debut in 3 of 2017's biggest trends: ruffles, polka dots and sheer fabrics and immediately skyrocketed to the top our all the best-dressed lists. Millie, then 13-years-old, completed her chic Rodarte mini with tough lace-up boots and a ballerina-esque bun.

J-Lo wears a silver sequined dress with high leg split20 of 20

Jennifer Lopez, 2018

Don't be fooled by the rocks that she's got, Jenny from the Block took to the red carpet a chain-mail Versace gown to accept the Video Vanguard Award before heading to the stage to perform a medley of hits, including "Love Don't Cost A Thing" and "On The Floor". J-Lo forever.

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