WWD Report Card: Red Carpet Guilty Pleasures

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

Cher: A-

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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+

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

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-

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+

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-

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

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-

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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