The Most Daring Red Carpet Dresses Of All Time

Published on 04/23/2020
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So many people all over the world await the Academy Awards every year. Besides waiting to see which of our favorite films will win the awards, but some of us more so than others look so forward to seeing our favorite celebs in their magnificent ensembles. The red carpet has always been filled with beautiful, stunning dresses and suits. Let’s not forget the occasional fashion blunders. Now, let’s take a short stroll down memory lane and rediscover the Oscars’ most memorable dresses! We guarantee all the best moments for you!

Kendall Jenner

Kendall Jenner is one of the sexiest models out there. She is very well-known for her family’s hit reality TV show, Keeping Up with the Kardashians. She reached ultimate stardom after becoming Victoria’s Secret model together with her BFF Bella and Gigi Hadid. In 2017, her dress for her red carpet appearance, was, let’s just say, left too little for the imagination.

Kendall Jenner1

Kendall Jenner

Rihanna

Rockstar RiRi is definitely not shy when it comes to challenging the rules & regulations of fashion. Typically, we admire her confidence when it comes to style, but this number might just be an exception. Fashion critics have gone as far as saying, “she resembled a bad bouquet for Valentine’s Day”. Oh RiRi, what happened?

Rihanna

Rihanna

Angelina Jolie

Without a doubt, there on not many people in the world that can truly succeed in wearing a pale-colored dress and certainly not with a pale complexion as well. Who else could do this, none other than Angelina Jolie, it seemed so simple and effortless for her. Not only does the dress look ravishing on her but it also shows off her amazing figure.

Angelina Jolie

Angelina Jolie

Andra Day

Turning heads with her extraordinary floral dress was other than Grammy-nominated, Andra Day. To complement her dress, her hair was styled in an extensive full ponytail decorated with cute pink flowers. She continued to unveil the drama with her very feminine dress by lying down on the red carpet!

Andra Day

Andra Day

Rita Moreno

The first appearance of this elegant gold and black boatneck gown was back in 1962. It was worn by Rita Moreno when she won Best Supporting Actress for playing Anita in West Side Story. And then again in 2018, she settled on wearing the classic piece once again, but this time she opted to add simple black satin gloves to complete her look. No doubt she is a magnificent iconic, right?

Rita Moreno

Rita Moreno

Nicole Kidman

During the 90th Academy Awards, Nicole Kidman looked absolutely astonishing in her Armani Privé dress. The unique structure of her cobalt blue gown fitted her like a glove! The deep blue color of the dress gave the perfect contrast to her light skin. She completed the look with a bold red lipstick. And we think she looks just amazing!

Nicole Kidman

Nicole Kidman

Cameron Diaz

Cameron Diaz has often topped many of the best-dressed lists, and we definitely understand why. Although this wrap dress she wore may not have been everyone’s cup of tea but it clearly showed us that Ms. Diaz is not afraid to experiment when it comes to fashion and style.

Cameron Diaz

Cameron Diaz

Kim Kardashian West

When it comes to fashion trends, it’s safe to say that Kim Kardashian-West is always on top of what’s trending. Shes often known for taking some risks when it comes to fashion and we also love to see how her taste has matured and evolved since she married Kanye West. She has a more classier and polished look, don’t you agree?  This dress is a great example…it hugs Kim’s figure perfectly!

Kim Kardashian West

Kim Kardashian West

Sarah Jessica Parker

Another famous style icon is Sarah Jessica Parker, much like her distinctive character in Sex and the City. However, many people think that she overstepped the mark with her extreme fashion choice back in 2015. All we can say is that she definitely turned heads with her out of the box ensemble.

Sarah Jessica Parker

Sarah Jessica Parker

Heidi Klum

As she is very used to strutting the catwalk, Heidi Klum is no stranger to red carpets. But, she may have missed the memo for this Oscar event as numerous people thought it was inappropriate for the occasion

Heidi Klum

Heidi Klum

Celine Dion

So many people actually considered the rocker chic look that Celine Dion went for to be a bit overboard. But then again it always refreshing to see celebrities venture out on their looks, but her outfit choice may have not been her best one.

Celine Dion

Celine Dion

Kate Upton

I think we can all agree that Kate Upton stole the spotlight at the Vanity Fair afterparty! She wore a simple, long black lowcut dress along with shoulder-length sparkling diamond earrings. The romantic look was completed with a matching black clutch as well as a couple of chunky rings and red lipstick. How gorgeous?

Kate Upton

Kate Upton

Daryl Hannah

During the time of the ’80s, Daryl Hannah became a fashionista trendsetter when she opted for this dazzling gold dress together with an elegant pair of elbow-length gloves. Her beautiful, long blonde waves flawlessly complemented her classy look during the 60th Academy Awards! She looks like a goddess!

Darryl Hannah

Darryl Hannah

Cindy Crawford

The gorgeous, long-legged supermodel Cindy Crawford can pretty much pull off any look. For her very first Oscars appearance, she chose a form-fitting Hervé Léger dress to boast her magnificent figure. And we think she looked amazing!

Cindy Crawford

Cindy Crawford

Savannah Chrisley

There is no doubt that this stunning 23-year-old actress will look absolutely exquisite in anything she wears. And when it came to this revealing black number, it was no different. It has been said that this has been her most sensual dress to date. Even though the design of the dress was not only form fitting but didn’t leave much for the imagination. Regardless, she completely nailed this look on the red carpet when she attended the ACM Awards.

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Savannah Chrisley

Miley Cyrus

We’ve all spotted Miley at multiple red carpet events and with no questions asked – she loves making a statement. Most of the time she opts for a more unconventional look that is bound to catch anyone’s attention. Take a look at her sleek black sequined Yves Saint Laurent gown that has a plunging neckline. To complete the look, she wore black sandals, chandelier earrings, a snake necklace, a bracelet, and multiple stacked rings. All the jewelry she wore was by Bvlgari.

Miley Cyrus

Miley Cyrus

Gal Gadot

Not only was she Wonder Woman in a solo film about her character but most people think she is the real-life version. Gal Gadot has made many stunning appearances on various red carpets, but here she looked truly magnet. When she attended the premiere of Wonder Woman in Hollywood, she wore a shimmering red Givenchy gown and looked as elegant as ever. This look has been regarded as one of her top 10 red carpets looks to date.

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Gal Gadot

Cardi B

We’re all very much aware that Cardi B is a huge fan of going all out on the red carpet. Here we see she wore a vintage Thierry Mugler look that came straight out of 1995. The dress had spectacular ruffles with pearl details at the neck and waist. The whole thing made her look like a pearl inside a clam, but only more stylish. She paired the dress with a matching pearl updo. Fun fact: this was the exact headpiece that was worn on the runway!

Cardi B

Cardi B

Taylor Swift

At the AMAs, Taylor outfit of choice was gold, gold, and more gold. She was also honored with Artist of the Decade award and performed a mix of her greatest hits on stage. Her outfit was a glittering gold bodysuit embellished with crystals along with fringe detailing. To finish the whole look, she wore matching gold block-heel booties with crystal-covered heels. Either way, she looked [au]some!

Taylor Swift

Taylor Swift

Geena Davis

What a throwback look, right? At the 1992 Academy Awards, Geena Davis was seen wearing a dress designed by Ruth Meyers and Bill Hargateat. The minidress was black and white with ruffles that genuinely made it look honestly made it look pretty much like a sophisticated costume. She completed her look by pairing it with a delicate pearl necklace and long gloves.

Geena Davis

Geena Davis

Kate Upton

I think we can all agree that Kate Upton stole the spotlight at the Vanity Fair afterparty! She wore a simple, long black lowcut dress along with shoulder-length sparkling diamond earrings. The romantic look was completed with a matching black clutch as well as a couple of chunky rings and red lipstick. How gorgeous?

Kate Upton

Kate Upton

Jennifer Lawrence

Jennifer Lawrence rocked a simple yet classy Dior gown that stole everyone’s hearts. We adore her sleek, tied back hair that complemented this chic look. Jen certainly looked exquisite.

Jennifer Lawrence 2013

Jennifer Lawrence

Melissa Rauch

Melissa Rauch never struck us as daring with her role in ‘The Big Bang Theory’ however, she is taking the carpet by storm and truly looks so different from how she does on the show. This spicy yellow gown, accentuates her tiny waist and hourglass figure perfectly. She has styled and accessorized the dress simply with pearl earrings and a white clutch bag.

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Melissa Rauch

Jennifer Lopez

In 2015, J.Lo was absolutely glowing and showed the world what kind of a fashionista she really is. She wore this jaw-dropping customized Elie Saab dress. The cut, shape, and color of the dress made her look like the belle of the ball! Every detail was perfect.

Jennifer Lopez

Jennifer Lopez

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