The Most Unforgettable Oscars Outfits Of All Time

Irina Shayk

This outfit caused a lot of controversy on the Red Carpet as she attended the famous yearly Vanity Fair Oscar Party. It is very daring, but we have to say wow she looks incredible.

Kate Upton

This model and actress is famous for her curves and assets. She leaves little to the imagination here at the Vanity Fair Oscars party, but she is definitely oozing Marilyn vibes.

Emma Thompson

This British beauty went absolutely flying, but didn’t let it get her downn, and shrugged it off, posing happily just after the red carpet mishap. You played that well Emma, very well.

Bella Hadid

This top model has big hopes and dreams, and has expressed her desire to take up acting and win a coveted Oscar one day. We are not sure about that, but one thing we do know, she absolutely killed it on the red carpet.

Cindy Crawford

What’s a supermodel to wear to her first Academy Awards? Well if you are Cindy Crawford, you could wear just about anything and look a million dollars. Of course she chose a body-hugging Herve Leger dress to show off her incredible figure.

Gigi Hadid

The top model and her sister always turn heads, no matter which red carpet event they attend. At the Vanity Fair party, Gigi’s cut out ensemble was definitely a crowd pleaser. But let’s be serious, when is she not?

Angelina Jolie

In the earlier days of her career Angelina Jolie was known for her eccentric bad girl escapades. At the 2010 Oscars, Jolie showed up with her brother on her arm. As the two walked the red carpet they shared a passionate kiss that left more than a few people feeling uncomfortable. We know brothers and sisters can be close-knit, but this Oscar moment is just a little too weird to explain.

Demi Moore

Demi Moore is usually known for looking demure on the red carpet but this early look of hers will go down in history as one of the very worst celebrity fashion choices. Are those bicycle shorts? Sorry Demi, but it’s a big no from us.

Sarah Jessica Parker

We’re all for being adventurous when it comes to fashion but Sarah Jessica Parker might have taken it one step too far. The star wore this interesting ensemble in 2015, ultimately turning quite a few heads, and not in a good way. We’re not sure the headgear was necessary.

Cher

Don’t get us wrong, we absolutely love Cher. She’s truly an icon! But even divas can get it horribly wrong sometimes. This is one of the most unflattering outfits we’ve seen on the superstar in a long, long time. Beading, satin and mesh detailing? Less is more, Cher!

Juliette Binoche

The nineties were an interesting time for fashion but this faux pas is difficult to forgive. Juliette Binoche showed up to the 1997 Oscars looking like something out of a B-grade horror movie. Made in brown velvet with an almost ridiculous Dracula-like collar, the dress was quite simply horrible. She may have walked away with the trophy but she certainly lost on the fashion front.

Trey Parer and Matt Stone

Trey Parer and Matt Stone are known for having great senses of humor. The South Park creators proved they were in it for the laughs when they showed up to the 1999 Academy Awards wearing dresses. They both donned looks reminiscent of Gwyneth Paltrow and Jennifer Lopez’s iconic fashion choices. We’re not quite sure whether to label this as a fail or a win?

Kendall Jenner

Kendall Jenner has risen to stardom, becoming one of the world’s hottest top models, alongside her best buds Gigi and Bella. She recently hit the red carpet, leaving little to the imagination, and that material with those heels, a recipe for disaster was just waiting to happen.

Hilary Swank

Swank won the Oscar this year (2000) for her show stopping performance in Million Dollar Baby. The plunging back really helped her make quite the entrance, and as she took to the stage to receive her award, she lit up the room.

Angelina Jolie

We wouldn’t have thought that such a pale color would work on the gothic actress, however, this dress complemented her to a T, and she looks absolutely beautiful. We are not sure that she seems so impressed, but we think she nailed it.

Kate Winslet

The Titanic star, is the epitome of English rose. She always looks stunning on the red carpet, and this dress is no exception. The red against her pale skin just accentuates her natural beauty. The cross shoulder detail just tops it off wonderfully we think.

Liz Hurley

Liz Hurley made a statement on this red carpet for a number of reasons. The man on her arm, her date for the evening was fellow British actor Hugh Grant. They became the ultimate couple. Her dress also caused a stir that evening, but we are not sure if it was for the right reasons but never the less, it became a memorable moment, that is for sure.

Cate Blanchett

Cate is another celeb who always gets it right when it comes to awards season, and this Armani Prive gown with 3D floral detailing was the perfect ode to old Hollywood glamor.

Lupita Nyong’o

Lupita Nyong’o definitely stole the show in this baby blue Prada gown. The floaty shape, the fabric, the neckline, it all just worked so well, there is nothing not to love about this look.

Amanda Seyfried

Amanda Seyfried just exuded demure on this Oscars night. Her Alexander McQueen gown, paired with her classic hairstyle, offered a timeless look.

Amy Adams

Well, what can we say? Amy Adams’ Oscar De La Renta look was definitely a memorable one in 2013. The American Hustle actress looked the picture of grace and elegance on the red carpet. Let’s see if she can top it this year.

Madonna

The queen of pop certainly made a statement with the King on her arm as her date. They both look very glamorous, head to toe in sparkles and fur. Oscars chic.

Cameron Diaz

Cameron usually nails her red carpet outfits. Yet this kimono-esque night gown is not quite what we think of when the Oscars comes to mind. Let’s hope this year she shocks in a better way.

Halle Berry

The actress wowed the crowd in this sheer number. Showing off her curves perfectly, this dress definitely was a winner, even if she didn’t go home with a gold statue.

Rihanna

Well well well, Ri Ri is definitely known for experimenting with fashion, but here she has really pushed the boat out. We are not quite sure if this is extremely innovative and revolutionary, or just a big no no. The pink eyes and cheeks just accentuate the fact that she looks like a valentines bouquet.

Zendaya

This young beauty, definitely made headlines with this number. Some have argued that she won the look for best dressed, while others have disagreed. What do you think. French Renaissance chic, or Les Miserable?

Faith Hill

What comes to mind when we see this dress are swizzles, the sherbet rainbow candy sticks. Faith you are very talented, but this dress is just truly an Oscars fail. The southern beauty will look amazing in anything, but the stylist missed the boat with this one.

Kim Basinger

When Kim Basinger walked across the stage at the 62nd Academy Awards, she looked more like Cinderella after running away from the ball. What is worse, is that she claims to have designed the horror movie like wedding dress herself.

Whoopi Golberg

We love this comedic actress so much, but we are unsure if this outfit was supposed to be a joke? She looks as if she hopped off a stage performance of the Wizard Of Oz.

Heidi Klum

This worldwide sensation has strutted her stuff on many catwalks and red carpets, but we are sorry to say that this dress should never have made it onto the red carpet.

Celine Dion

The singing sensation went for rock chic glam here, but we are not sure on what our verdict is. The dark eyes seem to sink into her face, and the silver sparkles feel a bit outer space to us. Stick to the singing Celine.

Miranda Kerr

The Victoria’s Secret Model never fails to impress, and certainly wowed in this number. There is definitely more skin on show than material here, but she is just perfection. Yet it doesn’t leave much to the imagination.

Gwyneth Paltrow

Oh Gwyn, yet again. Here she looks like a Barbie come to life. We do love the hair pulled back, but the baby pink gown is not doing it for us.

Kate Hudson

Kate Hudson, shone in this gold number. When it comes to the red carpet, she really has it down to a fine art. We wonder what she will pull out of the bag this year.

Charlize Theron

The South African beauty, radiated on the red carpet. Her tanned skin and blonde hair complemented the dress perfectly, and it is no wonder that this outfit is one of her finest moments. We cannot wait to see what she wears this year.

Michelle Williams

This statement dress, will go down as one of her best. The red lips against the yellow dress and her porcelain skin, just absolutely nailed it. Everything about this look is a red carpet winner to us.

Katy Perry

Katy Perry was definitely the talk of the town in this interesting outfit choice. Where do we even start? How do you make an impact on the most daring red carpet of the year? If you’re Katy Perry, it’s definitely about challenging our expectations.  Well she definitely made a lasting impression, that is for sure.

Emily Ratajkowski

This actress is a stunner and looks a million dollars in every outfit. This dress in particular caused a lot of head turning when she showed up to the Vanity Fair Oscars party last year.

Celine again

Who could forget the backwards tuxedo jacket Celine Dion rocked up in, at the Oscars in 1999? She was nominated here for her song prayer, but we think many prayed she came in another oufit.


Octavia Spencer

Octavia Spencer sparkled her way down the red carpet in Tadashi Shoji, when she accepted her Best Supporting Actress award for The Help in 2012.

Farah Fawcett

Farrah Fawcett was most definitely the golden girl of the ceremony in 1978. Her innovative Stephen Burrows gown inspired thousands of replicas for the disco.

Daryl Hannah

When Daryl Hannah paired elbow length gloves with her glamorous gold dress and long blonde waves at the 1988 Academy Awards, she got heads turning. We wonder how well this would go down this year.

Marion Cottilard

Marion Cotillard stood out on the red carpet in a Jean Paul Gaultier dress, embodying a mermaid. In the sea of tuille and sparkles, she definitely made a statement, and had the audience wishing they looked like her.

Zoe Saldana

Zoe Saldana made a statement at the 2010 Oscars where she wore a Givenchy Haute Couture with crystal embellished bodice, but it was the tulle ruffled skirt that made a lasting impression. It could have gone either way with this number, but we think she looked totally breathtaking.

Meryl Streep

Meryl Streep usually plays it safe, but this Lanvin number was a bold statement to make, and it totally worked. Streep also took home the gold for The Iron Lady that year. We love her.

Angelina Jolie

2012 was the year her dress went viral and inspired thousands of memes online. Angeline Jolie’s pose in her Atelier Versace gown with her left leg showing became known as “Angie leg.”

Jennifer Lawrence

Jennifer Lawrence has become sort of an Oscars sensation. Every year she manages to somehow tumble her way down the red carpet, or up the stairs to receive an award. Each year we look forward to seeing what will happen to Katnis Everdeen. She does always stumble in style, however.

Cher

Cher always pulls out all the stops when it comes to her Oscar outfits through the years. The Academy asked Cher to present the award for Best Supporting Actor this year and she definitely made an entrance. She stole the red carpet in this wild headpiece and black jewel-encrusted look.

Gwyneth Paltrow

Oh Gwyn. The only thing that comes to mind here really, is sack the stylist. This Ballerina inspired dress looks more like a Black Swan halloween costume that couture atelier gown. This was in her youth, we forgive and just hope she has learnt her lesson for this years upcoming soiree.

Bjork

Bjork’s egg laying swan dress most certainly made an impact, as it has gone down in history as one of the most memorable Oscars outfits of all time. We are not sure quite what she was thinking here. Maybe she was trying to channel Gaga vibes, but we are not sure she can pull it off.

Lady Gaga

Lady Gaga always gets away with pushing the boundaries, and she chose to do no different at the Academy Awards. Instead of playing it safe, she opted for a jump suit, still exuding class and timeless style.

Julia Roberts

The talented actress, has been named several years running as the most beautiful woman in the world, and here as she stood up to receive her award, she just glowed. Her dress was elegant and that train was on point.

Jennifer Lopez

JLo absolutely nailed it in this breathtaking Elie Saab gown in 2015. The neckline, the coloring, the shape, it all just works so well, and Jenny from the block certainly scrubs up well. This one of our favorite looks ever.

Penelope Cruz

This stunning Spanish actress totally wowed the red carpet here. The slicked back hair, paired with minimal jewels and that train, just absolutely hit it out of the park.

Jennifer Lawrence- 2

We love Katniss Everdeen and Jennifer even more. She always seems to have a red carpet tumble wherever she goes, but always plays it off so well. Here she rocked a simple but chic cropped top and skirt, and she looked beautiful.

Charlize again

Charlize wowed in this classic red Dior number on the red carpet. She has been affiliated with the French design house for years, appearing in their J’adore Dior fragrance advert. This gown was simple yet definitely left a mark on the red carpet.

Kim Kardashian West

KKW is known for some fashion faux pas on the red carpet. However thanks to her rapper come designer husband in tow, she dazzled on this red carpet.

ADVERTISEMENT