Rihanna, Cher, Britney Spears, Justin Timberlake and Barbra Streisand

A look back through time at some of the most memorable red carpet moments we can’t help but love.

Cher: A-


Cher, 1986 Oscars  Globe Photos/Shutterstock

She was a trailblazer, bringing stage costumes onto the carpet — and making it memorable. Who can forget this look, which was one of the high points of her collaboration with Bob Mackie? This showgirl get-up would not work on anyone else, but Cher turns this into one of our favorite guilty pleasures.

Barbra Streisand: B+

Watchf Associated Press Domestic News Entertainment California United States APHS56920 OSCARS STREISAND 1969 Actress and singer Barbra Streisand wears a sequined Arnold Scaasi bell-bottomed sheer pantsuit as she poses with her Oscar for her role in "Funny Girl" at the 41st Academy Awards in Los Angeles. Scaasi, whose flamboyant creations adorned first ladies, movie stars and socialites, died, at New York-Presbyterian Hospital of cardiac arrest. He was 85Obit Arnold Scaasi, Los Angeles, USA

Barbra Streisand, 1969 Oscars  George Birch/AP/Shutterstock

This is one of the earliest naked dresses in red carpet history. Her subversive tone with white cuffs and black bow creates the perfect tension between good girl meets vixen. This outfit is a perfect extension of her character in “Funny Girl.”

Lil Kim: B

MTV Music Awards New York, America 1999MTV MUSIC AWARDS, NEW YORK, AMERICA - SEPT 1999

Lil Kim, 1999 MTV Video Music Awards  Erik Pendzich/Shutterstock

It is very difficult to encapsulate a decade with one outfit, but Lil Kim clearly succeeded with this asymmetrical jumpsuit with matching pastie. This outfit is unforgettable.

Britney Spears and Justin Timberlake: A-

SPEARS TIMBERLAKE Show host Britney Spears, left, and Justin Timberlake of N'Sync arrive at the 28th Annual American Music Awards in Los AngelesAMERICAN MUSIC AWARDS, LOS ANGELES, USA

Britney Spears and Justin Timberlake, 2001 American Music Awards  Mark J Terrill/AP/Shutterstock

We will never look at Canadian tuxedos the same way again — as well as the best execution of couples coordinated outfit. It’s so bad that it’s good. Not only is it a guilty pleasure, it also joined the hall of fame for celebrity Halloween costumes, elevating it to iconic status.

Björk: B+

Bjork Singer Bjork, wearing a Marjan Pejoski swan gown, arrives at the 73rd annual Academy Awards, in Los Angeles. Bjork is nominated for best song for "I've Seen it All" from the film "Dancer in the Dark2001 Academy Awards, Los Angeles, USA

Björk, 2001 Oscars  Michael Caulfield/AP/Shutterstock

In 2001, Björk decided to dress like a swan to the Oscars, and the world was never the same. There is nothing pretty about the outfit, but the sheer confidence to dress like an animal at the biggest red carpet of them all gives her a spot in this guilty pleasures list.

Celine Dion: A-

DION Celine Dion, nominated for best song with "The Prayer" from the movie Quest for Camelot, arrives at the 71st Annual Academy Awards at the Dorothy Chandler Pavilion of the Los Angeles Music CenterOSCARS, LOS ANGELES, USA

Celine Dion, 1999 Oscars  Dave Caulkin/AP/Shutterstock

Today she is a fierce fashionista, but that wasn’t always the case. With this backward Galliano suit in 1999, she surely turned heads, and it got her a good amount of negative press. But she caught the attention of the fashion elite then — and has never looked back.

Rihanna: A

Rihanna2014 CFDA Fashion Awards, New York, America - 02 Jun 2014WEARING ADAM SELMAN

Rihanna, 2014 CFDA Fashion Awards  Marion Curtis/Starpix/Shutterstock

When it comes to Rihanna there are a variety of guilty pleasure moments. But this naked dress golden era meets Marilyn Monroe look is both ultra chic and steaming hot. There have been other, much more bombastic red carpet moments from her, but this is an instant classic.

Ezra Miller: A-

Ezra Miller'Fantastic Beasts: The Crimes of Grindelwald' film premiere, Paris, France - 08 Nov 2018Wearing Moncler x Pierpaolo Piccioli

Ezra Miller, 2018 “Fantastic Beasts: The Crimes of Grindelwald” premiere  PDN/SIPA/Shutterstock

When it comes to men’s wear, things have changed dramatically in the past few years, and Miller is one of the leading forces in this new movement. This black, witchy Pierpaolo Piccioli for Moncler coat/gown with matching black lipstick was thought of as a runway-only outfit — until Miller showed us otherwise.

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