Lindsey Sirera
Updated July 18, 2019
Jon Kopaloff, FilmMagic

The red carpet is no place for the fashion meek. There are ridiculously good looks that saunter down a step and repeat all the time, but very few celebrities actually traverse into the most daring red carpet gown category, aka almost naked. Which is what makes the outfits on our list so very special.

Boring, they are not. Forgettable, they could never be. These are the crème de la crème of daring red carpet ensembles, the ones we could only hope to wear in our wildest dreams, but that the women rocking them make look so dayum easy. Of course, Bad Girl RiRi tops the list. She basically wrote the book on daring fashion, and that’s one of the many reasons we revere her style. Kim Kardashian and Beyoncé are also in this elite sartorial category, with sultry nearly naked dresses of their own.

Now, a “daring dress” doesn’t always mean long gown either, as evidenced by Bjork’s 2001 Oscars ensemble. And Miley Cyrus’ addition to the list is more chandelier than dress, but we’ll take it. Clearly, there are quite a few daring red carpet looks worthy of our praise. Now free to ohh and ahh over the assortment of said dresses below.

1Kendall Jenner, 2019

Axelle/Bauer-Griffin, Getty Images

Kendall knows her way around the red carpet, and she left very little to the imagination in her Vanity Fair Oscar Party look.

2Emma Roberts, 2019

Jean-Baptiste Lacroix, Getty Images

So delicate, so chic—we can always count on Emma to serve a sexy yet classy lewk.

3Alessandra Ambrosio, 2018

Jean-Baptiste Lacroix, Getty Images

Golden goddess Alessandra is glowing in this gorgeous getup.

4Gabrielle Union, 2017

Pascal Le Segretain, Getty Images

One leg in and one leg out of this sexy dress is giving us major heart eyes.

5Lady Gaga, 2017

CBS, Getty Images

Obviously, Lady Gaga has never been one to shy away from a statement look, and her 2017 Grammy’s red carpet ensemble was definitely that.

6Jennifer Lopez, 2017

Jason Koerner, Getty Images

If you’ve got it, flaunt it, right? J.Lo definitely lives by this phrase when it comes to her red carpet looks, and we’re all about it.

7Rihanna, 2017

Jon Kopaloff, Getty Images

Bad Girl RiRi is the reigning queen of daring fashion, and this Tom Ford bra-gown shows why.

8Bella Thorne, 2016

Jeff Kravitz, Getty Images

Bella bared it all in this stunning, curve-hugging gown.

9Bella Hadid, 2016

Michael Stewart, Getty Images

We’re getting elegant zebra vibes from Bella wearing these glittery stripes.

10Rita Ora, 2015

Pascal Le Segretain, Getty Images

Cue the jaw drop! We can’t forget Rita in this Donna Karan number.

11Irina Shayk, 2015

Pascal Le Segretain, Getty Images

Mwuah! Irina was not afraid to rock it in this slinky Versace jumpsuit-dress.

12Miley Cyrus, 2015

Jason Meritt, Getty Images

At first glance, we thought this Versace dress was actually a chandelier. Regardless, Miley rocked it.

13Beyoncé, 2015

Axelle/Bauer-Griffin, Getty Images

Queen Bey in Givenchy just plain shut. it. down.

14Amber Rose, 2014

Jason Merritt, Getty Images for MTV

Amber Rose stuns in this chain-link Laura Dewitt dress.

15Rihanna, 2014

Dimitrios Kambouris, Getty Images

Behold: The most daring red carpet dress of all time, courtesy of Rihanna and Adam Selman.

16Kim Kardashian, 2013

Larry Busacca, Getty Images

Feathers, crystals, and a whole lot of see-through fabric qualify this Roberto Cavalli design for the best naked dress category.

17Toni Braxton, 2001

Terry McGinnis, WireImage, Getty Images

She’s a Grammy-winner, and she’ll wear what she wants.

18Bjork, 2001

Jeffrey Mayer, WireImage, Getty Images

It doesn’t get more daring than wearing a swan. (The dress is by Marjan Pejoski.)

19Jennifer Lopez, 2000

Scott Gries, ImageDirect

This Versace number is so iconic, they’re *still* making repeat versions nearly two decades later.

20Lil’ Kim, 1999

Kevin Mazur, WireImage

Pasties weren’t a thing until Lil’ Kim made them a thing.

21Elizabeth Hurley, 1994

Dave Benett, Hulton Archive, Getty Images

This Versace dress basically created the side cutout trend.

Nearly naked dresses are clearly red carpet showstoppers, and this trend has stood the test of time.