The Most Stunning & Daring Red Carpet Dresses Of All Time

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Gwyneth Paltrow

All eyes are on this A-lister when she steps out at any awards ceremony, but perhaps in 2002 she went a little far. Her Alexander McQueen number was called ‘the worst dress ever’, which isn’t what anyone is aiming for. Alexander McQueen himself said that she looked incredible, but Gwyneth admits she wishes she had done some things differently. “I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to – a little bit of punk at the Oscars.”

Sandra Bullock

This is one of those love/hate designs that could go either way. While the top of the dress is simple and elegant, it lifts out into two fluffy feathered stripes which are certainly an acquired taste! This dress was an Oscar de la Renta classic, which was previously in black, but redone in white. It would be another six years before she won the Best Actress award for her role in The Blind Side, but her fashion choices hit the headlines many times before then.

Sandra Bullock

Cher

This is one lady who always sets tongues wagging with her incredible style choices, as well as being known for dressing to astound on the red carpet! So no one was surprised to see Cher in all her glory stepping out in this Bob Mackie number at the 1998 Oscars. She laughed off the criticism she received for this ensemble, saying “If you want to look the same as everyone else, you should be going to the Seatback Convention — not the Oscars. I thought we were in show business!”

Halle Berry

In 2002, Halle Berry showed that sheer can work in your favor with a stunning Elie Saab dress which had everyone talking. While the full skirt was made of silk, the bodice was sheer, with the help of strategically placed embroidery of course! It was the right night to impress the media, as she was awarded the Best Actress award for her incredible role in Monster’s Ball, along with the late Heath Ledger. The dress stands as one of the best in red carpet history.

Rihanna

Rihanna is known as much for her show stopping fashion as her show stopping voice. This red carpet superstar knows how to get attention to herself, and in this photo you can see she wears this incredible yellow gown with the largest train we’ve ever seen. Half Disney princess, half gorgeous peacock, and teamed with the highest heels we’ve ever seen, she certainly stole the show. The diva looks entirely flawless.

Rihanna

Jennifer Lawrence

There’s almost nobody in the world ho can say a bad thing about J Law. Her acting skills are second to none, and her down-to-Earth personality is something that we all can relate to. She likes to keep it real, despite her worldwide fame and enormous fortune. So for the Red Carpet, she went with an interesting sheer grey dress, with a simple black bodysuit underneath to cover up the important parts.

Tilda Swinton

Lanvin tends to get it right, and many actresses use them as a way to get an effortless win when they head to an awards ceremony. They have been known to dress some of Hollywood’s biggest stars such as Beyonce, Kim Kardashian and Meryl Streep. But in 2008, Tilda Swinton came under fashion fire for wearing this dress, which people said looked like a trash bag. Ouch. It certainly does look oddly shiny from certain angles, and drapes off her in a not very flattering way.

Marion Cottilard

In 2008, Marion Cottilard became the first French Actress to win the coveted Best Actress award at the Oscars for her role in La Mome. The next year she knew she would be center stage again, so certainly dressed to impress. This incredible gown turned heads with its full skirt which took volume to a whole new level. The simple jewellery she wore with it, as well as subtle make up made sure that she didn’t take the look too far.

Marion Cottilard

Helena Bonham Carter

This actress is known for splitting the crowds with her crazy unique style. At the 2013 Oscars she stunned the crowds with this feathery layered dress, which she worked on with Colleen Atwood. Some said it was the best she had looked at the Oscars, while others said that this was a real fashion faux-pas. She had been nominated for Best Supporting Actress in 2011, for her role in The King’s Speech, but this was a low-key year for her.

Helena Bonham Carter

Miley Cyrus

In recent years this little lady has turned head for her provocative and obscure outfits and behaviours.  But recently her style has mellowed out and she has toned down the shock appeal when it came to her public appearances. Miley Cyrus has dazzled us with her talent, charm, and now elegant red carpet gowns. This particular ruby red gown was worn to the Grammys, where she performed with Elton John. Miley, you are a true gem in this stunning dress.

Carey Mulligan

AT the 2010 Oscars, Carey Mulligan wore a Prada dress which got everyone talking. From a distance it looks like it’s covered in miniature gems and sparkles. Up close, you can see that the design is really dozens of nuts, bolts and even tiny utensils! Miuccia Prada designed the dress, but we wonder whether Prada would have been too happy by what happened at the end of the night. “I got drunk at the end of the night and started ripping them off and giving them as presents to people, so that was fun. I’m pretty sure that was the point of it!”

Carey Mulligan

Whoopi Goldberg

Whoopi might hold the award for the most famously bad Oscar outfit of all time. This paisley pantsuit is as bold as can be, in lime green and purple. She wore it for the 1993 Oscars. In 1991 she won Best Supporting Actress at the Academy Awards, but in 1993, the biggest talking point was definitely going to be her outfit choice. It didn’t help with easy headlines that she had also acted in the movie, The Color Purple. Ouch.

Halle Berry

It looks like Halle Berry just can’t lose on the red carpet, and when she stepped out in 2013 in a stunning custom made Atelier Versace design, the response was breath taking. The dress featured a plunging neckline and unique stripe detail, as well as a mesh beading. She was invited to introduce the James Bond tribute, so all eyes were truly on her. As the first black actress to win Best Actress at the Oscars, she is a role model for many people of color.

Halle Berry 2013 oscars

Angelina Jolie

At the 2000 Oscars, Angelina Jolie decided to channel her inner Goth with a striking black gown which might have been a little more Morticia Addams than she originally planned for. The look surprised and delighted the media, who were used to more classic cocktail dresses and spaghetti straps. This was the year she won Best Supporting Actress for her role in Girl, Interrupted, so we can see why she chose to go with her inner darkness.

Bjork

The Bjork swan dress is probably the most memorable Oscar outfit of all time. Bjork wore it in 2001 for the award ceremony, shocking many people on the red carpet. At the ceremony, Bjork mimed laying an egg directly onto the carpet! Bjork herself wore the dress again for her next album cover, and it has been emulated many times, including by Ellen DeGeneres at the Emmy awards, and then reimagined by Valentino at the 2014 Spring Couture fashion show.

Meryl Streep

Meryl is the undisputed Queen of Hollywood, and on the year she picked up the Best Actress award for Kramer vs Kramer, she also stole the show with a gold lame Lanvin gown. Some people weren’t too impressed with the dress, saying that she was mimicking the trophy she so coveted! Seeing as she walked away with the top spot, we would say she had the last laugh, a role model and style icon for women everywhere, and a deserving winner.

Meryl Streep

Vera Farmiga

Vera has been an actress for many years, but it’s her roles in The Departed and Up in the Air which really caught our attention. At the 2010 Oscars she wore this incredibly eye catching gown in the brightest of berry pinks, complete with ruffles and folds galore. The dress was a Marchesa, and she complemented it with matching lipstick, and subtle jewellery. She stole the limelight away from many younger actresses that night!

Hilary Swank

Voted the 16th greatest red carpet dress of all time, this Guy Laroche dress turned heads in 2005. Completely backless, but covered up from the front, Hilary Swank looked entirely flawless, and put her firmly on the best dressed list. Almost aptly, this was the year that she won Best Actress for Million Dollar Baby, and many said that she totally dressed the part. This dress is one of the most famous Oscar outfits of all time.

Hilary Swank

Diane Keaton

Proving her place as a fashion risk taker is pretty difficult with all eyes on you at an event as important as the Oscars. Diane Keaton found herself effortlessly cool with her unique trouser suit idea for the Academy Awards. In 2004, this may well have been a little head of its time, and she recognizes that sometimes her fashion choices result in her ending up on some ‘worst dressed’ lists. She shrugs this off, and is happy being herself. And we love her for it!

Charlize Theron

Here is Charlize again, stunning the crowds with this amazing dress by Dior in 2006. This dress proves that you win some you lose some, as while the critics didn’t like her 2010 ‘rosebud’ number, this was one outfit which they went wild for. Complex and yet elegant, this dress could keep you talking all night, and it certainly did! Just two years previously she had walked away with Best Actress for Monster, and she was nominated again that night for North Country.

Celine Dion

In 1999, Celine Dion stunned her fans with her iconic backwards tuxedo, designed by John Galliano. Many people said she looked crazy, with pants which were ‘far too big’ and that the whole look was just wrong. She recently spoke up for that outfit choice, including telling People magazine that perhaps it was a bit ahead of its time, and would have fared better on the red carpet today, rather than almost 2 decades ago. She has zero regrets.

Celine Dion 1995 oscars

Jada Pinkett Smith

Will Smith’s other half has had some incredible red carpet wins in her time, and stunned the media and the public alike with her awesome dress sense. But this year has to be a bit of a fail. The white and yellow dress cuts her in half in quite an unflattering way, and the shiny pattern in the full skirt looks cheap and flashy rather than stylish and elegant. She even looks like she knows she could have done better with her style this year, uncomfortable on the carpet.

Melissa George

This Dolce and Gabbana gown came with the trendiest mermaid style we’ve ever seen, giving Melissa George effortless elegance on the red carpet here in 2009. She paired it with a lovely simple white clutch and some very understated jewellery to go alongside. If it were us, we’d spend the evening worried about someone spilling their wine on us, but she seems to pull off that glistening clean look pretty well.

Melissa George

Beyonce

When you know you’re going to be on display, you want to look your very best. But when you’re Queen Bey, and you always look pretty awesome, the Oscars are a time to pull out all those stops. For the 2009 Oscars, Beyonce was performing in front of millions, and her dress was certainly a show –stopper. We love the gorgeous material that just makes you want to touch it, and those striking gold roses. Breath taking.

Beyonce

Uma Thurman

Who wouldn’t want to wear a bit of white and ruffled after spending so much time on the set of Kill Bill? Uma Thurman went for almost the exact opposite of her costuming when she stepped onto the 2004 red carpet at the Oscar ceremony, and she is still being picked apart for her outfit choice today. Billowing and oddly cut, with a bright blue belt holding it all together, it’s certainly not the most obvious look for the evening.

Cameron Diaz

This Asian-inspired floral gown split the critics at the time, and it’s still under a lot of scrutiny. Is it gorgeous and timeless, or does it look like someone’s dressing gown? Is it a great alternative to the more uptight cocktail dresses we usually see at the Academy Awards, or is it far too simple and casual for such an important event? Cameron paired the dress with understated jewellery and some simple peep toe shoes, and she looks effortlessly at home on the red carpet.

Lizzy Gardiner

If you’re a costume designer, people are going to expect more from you than your average red carpet dress, and you’re clearly going to design something yourself, which is a bit more out of the box. Gardiner certainly did that, with this unique dress made of 254 American Express cards. While people were mean about the design, it was auctioned off to give over $12,000 to AIDS research, and that very night Lizzy Gardiner won an Oscar for Best Costume Design. So who’s laughing?

lizzy gardiner

Trey Parker and Matt Stone

Some people take the Oscars seriously, while others… don’t. When Matt Stone and Trey Parker, better known as the creators of South Park, were nominated for Best Original Song in 2000, they decided to take the whole thing extremely lightly. They showed up in full drag gear for the red carpet, and reportedly got high on Acid before having a friendly chat with some reporters and media attendants. They didn’t win the award, and that’s probably just as well!

Jennifer Lopez

This Giorgio Armani Prive gown turned heads at the 2010 oscars, with many saying the extra material was unnecessary and ruined the dress, and others disagreeing entirely, loving the unique style. Jennifer Lopez is all about body confidence, and we think she looks radiant, showing that there is no right shape or look for the red carpet, it’s all about flaunting what you have, and holding your head high while you do it.

Jennifer Lopez

Vanessa Paradis

An actress, model and musician, Paradis is actually a spokesperson for Chanel, so it’s not surprising that she stepped onto the red carpet in this Chanel design. On her arm is none other than her at the time boyfriend Johnny Depp, but the pair make rather a gloomy image. The neck scarf and black clutch seem just a bit too much black for this happy occasion. While Johnny tries to brighten things up with his navy suit, it doesn’t quite work.

Sharon Stone

In 1998, Sharon Stone fought against the red carpet culture when she decided to eschew the designer trend for her stroll across the world’s most famous carpet. In fact, she wore a white button down shirt, which was reportedly from the Gap, and might well have been her husbands! Ok, she wore it with a Vera Wang skirt, but it was still pretty low key for such an auspicious event. Two years earlier, she chose a Gap turtleneck for the event, showing this isn’t just a one off for her.

Susan Sarandon

In 1996, Susan Sarandon won the Best Actress Academy Award for her role in Dead Man Walking. But it wasn’t just her talent as one of the world’s greatest actresses which had people talking. She wore a truly gigantic brown gown, stealing the show and totally owning it. Alongside her cropped haircut and very understated make up and jewellery, the dress was a real statement, and one which people still talk about today.

Charlize Theron

On the red carpet at the 2010 Academy Awards, this number by Charlize Theron certainly turned heads, especially the er… midsection! The Orange County Register said “We hated the weird rosebud pasties on her strapless, flowing lavender and mauve gown. All the attention in the wrong place.” Charlize was totally nonplussed by references to the cinnamon buns on her chest, gushing about how much she loved her dress to US Magazine. You go, girl.

Charlize Theron 2010 oscar dress

Cate Blanchett

This Givenchy classic turned a lot of heads at the 2011 Oscars, but not all of them were complimentary. Despite it being totally on trend, the weird middle plate section gave critics a bit of a field day, as well as the demure pose which Blanchett took on the red carpet itself. She didn’t win any awards that year, but the dress is certainly one for the memory books. And just 3 years later she would walk away with the most coveted Best Actress award for Blue Jasmine.

Cate Blanchett

Nicole Kidman

Some people hit the headlines because their dresses are outrageous, or out of the box, designed by someone particular, or even self designed for the awards ceremony of the year. Nicole Kidman turned heads for different reasons in 1997 when she took to the red carpet in this Dior classic. The designer reportedly paid her a staggering $2 million to wear the dress on the red carpet, making it one of the most expensive pay outs of all time for an awards outfit.

Heidi Klum

Heidi Klum can probably turn heads wearing her pyjamas, so it’s unsurprising that her red carpet outfits are the talk of the town. This incredible outfit choice was custom designed by John Galliano of Dior, and she looks the most confident she could be as she shows it off, complete with a simple red clutch purse. Red can sometimes be a risky color choice, as it could end up clashing with the carpet itself, but Klum pulls it off in true style.

Heidi Klum

Kim Basinger

If we’re going to find one red carpet outfit which we can get everyone to agree on, it’s probably this self-designed outfit by Kim Basinger, which she wore to the 1990 Oscar awards. It might be that it’s over 25 years old, or it might be just timelessly tragic, but no one understood what she was thinking. One sleeve, giant skirt, strange material… this one was just no all over. We wonder if the glove was a last minute addition, or part of the ensemble?

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