There is no doubt people from around the world look forward to the Oscars every year. Celebrities must plan far in advance for this special event, and we patiently wait to see not only who wins awards but also to judge their fashion choices. There are always beautiful, bright gowns, over the top fashionista dresses and of course the extreme, unforgettable, fashion faux pas.
Kendall Jenner
This has been an extraordinary year for Kendall Jenner. Her stardom has taken a huge rise, as she became one of the world’s top models alongside her best buds Gigi and Bella Hadid. Her 2017 red carpet dress leaves little to the imagination. It shows off her naturally thin and fit figure, and hugs her curves in all the right places. We love it!
Kendall Jenner
Miranda Kerr
The Victoria’s Secret Model always looks amazing and she looks as sexy as ever in this red dress. She proudly displays quite a bit of skin with this look, and we think there might be more skin on display than material. She leaves little to the imagination and it totally works.
Miranda Kerr
Hilary Swank
Swank won an award and on the red carpet in 2000. She won the Oscar for Million Dollar Baby and she lit up the room in this beautiful, elegant blue dress.
Hilary Swank
Farah Fawcett
Farrah Fawcett wore a beautiful, golden Stephen Burrows gown in 1978. This dress was certainly memorable and thousand of girls copied the dress after she wore it.
Farah Fawcett
Irina Shayk
Irina’s dress was the topic of the night for many people. It is certainly revealing. We think she looks gorgeous!
Irina Shayk
Gigi Hadid
The super famous, top model and her sister have always turned heads. We wish we had their genes and bone structure! No matter which event she attends, Gigi looks stunning. This decision is no exception.
Gigi Hadid1
Charlize Theron
While some like to criticize the South African beauty’s skin and hair, we think it complements the dress perfectly. We also think this is one of her finest red carpet moments. Do you agree?
Screenshot 7
Rihanna
Our favorite bad girl, Ri Ri is well known for taking fashion risks. We usually are big fans of her style, but we aren’t quite sure she pulls this one off. Some fashion experts have commented she looks like an unflattering Valentine’s Day bouquet.
Rihanna
Angelina Jolie
Usually, such a pale-colored dress wouldn’t complement such a pale complexion. In this case, however, it totally works! This dress definitely complements her figure and she looks absolutely beautiful. While her face might look less than impressed, we think she nailed it.
Angelina Jolie
Katy Perry
Katy Perry certainly started some controversy over this interesting outfit decision. Whether you love this look or hate it, we think Katy Perry achieved her goal of making a huge impact on the red carpet and challenging our expectations of how a woman should dress for this event.
Katy Perry
Andra Day
The 2018 look of Andra Day certainly caught eyes with its array of materials and colors. The Grammy-nominated singer, Andra Day, turned heads both with this dress and by lying down on the red carpet! She added more drama with her hairstyle decision. The voluminous ponytail full with loose waves was gorgeously decorated with small pink flowers. We certainly think this is a totally original, girly look.
Andra Day
Sarah Jessica Parker
SJP is well known for her adventurous and experimental fashion sense. Some have said she went one step too far with this 2015 look. She definitely turned heads with both the dress and the headgear.
Sarah Jessica Parker
Daryl Hannah
In 1988 when Daryl Hannah paired elbow-length gloves with this glamorous gold dress and long blonde waves, she certainly turned heads. We commend her for this look, especially in the ’80s!
Darryl Hannah
Jennifer Lopez
In 2015, Jennifer shined in this Elie Saab gown. Every detail is perfection: the neckline, the coloring, the shape, it all just works so well!
Jennifer Lopez
Jennifer Lawrence
Jennifer Lawrence became the face of Dior in 2012 and we can see why. She looks graceful and gorgeous in her gown.
Jennifer Lawrence 2013
Miley Cyrus
Miley Cyrus is known to make a statement while on the red carpet; more often than not, she opts for edgy looks that will definitely catch your eye. Here we can see she went with a black sequined Yves Saint Laurent gown with a plunging neckline. She paired it with black sandals, chandelier earrings, a snake necklace, a thick bracelet, and multiple stacked rings. All her jewelry was by Bvlgari.
Miley Cyrus
Cardi B
Cardi B showed up with a vintage Thierry Mugler look straight from 1995. The dress featured dramatic ruffles with pearl details at the waist and neck. The entire ensemble was made to resemble a pearl inside a clam but in a fashionable way. Cardi paired the dress with a matching pearl updo. In fact, this was the same piece that was worn on the runway.
Cardi B
Penelope Cruz
Penelope looks so beautiful! We love the dress, her simple hair, and simple jewelry.
Penelope Cruz
Taylor Swift
At this year’s AMAs, Taylor Swift went for gold for her onstage outfit. The singer was honored with the Artist of the Decade award and performed a medley of her greatest hits on stage. She sported a glittering gold bodysuit embellished with crystals and fringe detailing. To complete the look, she wore gold block-heel ankle boots with pointed toes and crystal-covered heels.
Taylor Swift
Blac Chyna
31-year-old Blac Chyna attended the Oscars for the first time in 2020. She showed up wearing a black high-slit low-cut Dona Matoshi gown that featured embroidered shoulders to the show. To complete her look, she paired the dress with coordinating Jimmy Choo heels and large matching blue earrings. She attended the event with Christopher Trujillo, the record producer, and recording engineer as his plus one.
Blac Chyna
Geena Davis
This one is more of a throwback. Here we have Geena Davis at the 1992 Academy Awards wearing a dress designed by Ruth Meyers and Bill Hargateat. The black and white ruffled minidress had ruffles that made it look somewhat like an elaborate costume. She paired it with long gloves.
Geena Davis
Melissa Rauch
Often seen as an underdog on ‘The Big Bang Story’ Melissa Rauch takes the red carpet by storm, that’s for sure. The star recently announced an exciting pregnancy. She is seen here in a breathtaking yellow dress that is rouched and cinched around the waist area, the color is beautifully bold and daring for someone with such a fair complexion.
Melissa Rauch
Jennifer Aniston
Jennifer Aniston doesn’t always wear red, but when she does, wow! She looks stunning in this crimson Valentino Haute Couture gown at the 2013 Oscars.
Jennifer Aniston
Salma Hayek
Just at this last Oscars, Salma Hayek wore a purple Gucci dress with a beautiful diamond Harry Winston chain. We can’t believe she is 51 years old!
Salma Hayek
Emily Ratajkowski
Emily Ratajkowski is a gorgeous woman and we love this dress on her. We think she looks like a million dollars. She looks great in black and the shape of this dress is very flattering on her sexy figure.
Emily Ratajkowski
Cindy Crawford
Beautiful, supermodel Cindy Crawford would wear just about anything and look gorgeous. For her first-ever Academy Award’s she picked a winner. This body-hugging Herve Leger dress shows off her incredible figure and we think she looks awesome.
Cindy Crawford
Heidi Klum
Heidi Klum is used to strutting her stuff on many catwalks and red carpets. This purple gown is definitely girly, but some have said it was not an appropriate choice for this event.
Heidi Klum
Celine Dion
Celine Dion decided to take a risk and go for a rock chic glam look here. We aren’t sure the dark makeup or the dress was her best style choice.
Celine Dion
Cameron Diaz
Cameron Diaz is used to being at the top of the best-dressed list. While this kimono-esque nightgown might not be everyone’s favorite look, it is certainly bold and memorable.
Cameron Diaz
Kim Kardashian West
Fashionista KKW is known for taken fashion risks and being on top of trends in the design world. Since her marriage to Kanye West, we think her style has matured and improved. This dress is a great example. We think this dress is elegant and classy, and it hugs her figure in all the right places.
Kim Kardashian West
Demi Moore
Demi Moore really surprised us with this look. She usually dresses way more chic. Wither you love this dress or not, it is undeniable that she looks extremely happy wearing this interesting dress.
Demi Moore
Cher
We absolutely love Cher! She is absolutely an icon but even total divas can wear not the most flattering looks. Some style critics called this look “unflattering.” We aren’t sure about the dress, but we dig the wig!
Cher
Lady Gaga
Lady Gaga always is always pushing the boundaries and is an amazing fashion trend setter. This outfit certainly fits the bill. Lady Gaga’s style has certainly evolved and this jump suit exudes class and timeless style.
Lady Gaga
Juliette Binoche
The nineties were an interesting time for fashion. This one is not easy to forget. Juliette Binoche’s 1997 Oscars look was this dress made from brown velvet. Some might not give the dress an award, but she walked with the Best Supporting Actress Award during this show.
Juliette Binoche
Kate Winslet
Kate Winslet always looks stunning on and off the red carpet. We totally think this dress suits her with both the cut and the color. Against her pale skin this dress really accentuates her natural beauty. Nice choice, Kate! You look like the epitome of a beautiful English rose!
Kate Winslet
Liz Hurley
Liz Hurley started a wave of controversy in 1995 not only due to this dress, but also the man on her arm. Her date this year was fellow British actor, Huge Grant. They later went on to become the ultimate Hollywood couple.
Liz Hurley
Cate Blanchett
Cate Blanchett is one amazing woman who seems to always get it right with her fashion choices during awards seasons. This Armani Prive gown complete with the 3D floral detailing was a well down ode to old Hollywood glamor.
Cate Blanchett
Lupita Nyong’o
Lupita Nyong’o wore this amazing custom baby blue prada gown to the 2014 awards. Everything about this dress works on her. The floating shape, cut, neckline, everything! We think there is not one flaw in this look and it is one of our all time favorite celebrity dresses.
Lupita
Amanda Seyfried
Amanda Seyfried really owned this Alexander McQueen gown. We think she made a great decision with both the dress and her classic hairstyle. It offers a beautiful, timeless look that we just adore.
Amanda Seyfried
Amy Adams
We love Amy Adams’ style and this Oscar De La Renta dress is no exception. The American Hustle actress looked like the epitome of elegance at the 2013 awards. We aren’t sure she can top this look. Well done, Amy!
Amy Adams
Zendaya
This young beauty stirred up a wave of controversy with this dress. Some fashion critics think this risk deserves a place on the best dressed list, while others strongly disagree. Do you think this is a fashion win or a huge faux pas?
Zendaya
Faith Hill
Faith has said in many interviews she likes to dress how she feels. She must have felt very happy on this day because she chose to wear the happiest summer colors. While some people aren’t a huge fan of this look, we think she looks jovial and that is very attractive on its own.
Faith Hill
Kim Basinger
Kim Baginer designed this dress herself and it definitely is an unforgettable look. She rocked this white Cinderella look during the 62nd Academy Awards where she won Best Actress in a Supporting Role for her work in L.A. Confidential.
Kim Bassinger
Whoopi Golberg
We love this comedic actress to death, and if her goal was to put a smile on our face with this look she definitely achieved that.
Whoopi
Gwyneth Paltrow
There is no Oscar Dress list without Gwen’s infamous pink dress. We love everything about this look from the dress to the hair. She looks like a perfect real life Barbie doll. This look is definitely unforgettable.
Gwenyth Paltrow1
Kate Hudson
Kate Hudson definitely has a classy, glamour style, and this look reflects that. She has perfected the art of looking amazing on the red carpet and we wonder every year how she will look.
Kate Hudson
Michelle Williams
Michelle Williams is beautiful and this dress is definitely one of her best fashion decisions ever. She nails it with the red lips against the yellow dress and her porcelain skin. Everything about this look is red carpet perfection.
Michelle Williams
Celine, Again
Back in 1999, Celine Dion wore a backwards tuxedo. There were mixed opinions about this look, but we think it is awesome whenever a celebrity takes a risk!
Celine Dions 2nd Look
Octavia Spencer
Octavia Spencer looked amazing in this dress. That night she won the award for Best Supporting Actress.
Octavia Spencer
Marion Cottilard
Marion Cotillard shined in a beautiful, mermaid like Jean Paul Gaultier dress.
Marion Cottilard
Zoe Saldana
In 2010, Zoe Saldana wore a Givenchy Haute Couture with crystal embellished bodice and a tulle ruffled skirt that made heads turn. Simply beautiful!
Zoe Saldana
Meryl Streep
Meryl Streep made a statement in this gold Lanvin dress. It absolutely works and she looks great!
Meryl Streep
Halle Berry
This dress definitiely made headlines! Halle looked beautiful in this sheer dress. The maroon looks beautiful against her skin and it shows off her figure in a very classy way. This dress is a winner in our book!
Halle Berry
Angelina Jolie
In 2012 Angelina wore an Atelier Versace dress. Her pose showing off one leg went viral because she looked so beautiful!
Angelinas 2nd Look
Cher, Again
This dress is definitely iconic. Cher stole the red carpet in this wild headpiece and black jewel-encrusted look.
Chers 2nd Look
Bjork
This swan dress is definitely an unforgettable Oscar moment. We commend Bjork for taking a risk, but this might not be her best look.
Bjork
Julia Roberts
Julia Roberts looked stunning and classic in this dress. We love the train in the back.
Julia Roberts
Bella Hadid
No wonder Bella is one of the top models in the world! Her body looks amazing in this sexy red dress.
Bella Hadid
Jennifer Lawrence, Again
Jennifer Lawrence rocked a simple but chic cropped top and skirt, and she looked beautiful. We love her smoky eyes and sleek haircut. Everything goes so well together!
Jennifer Lawrence Again
Charlize, Again
Charlize knows how to wear color. She wowed in this red Dior dress.
Charlize Theron
Madonna
The queen of pop resembled Marilyn Monroe in this beautiful look. We think she looks stunning!
Madonna
Whitney Houston
Whitney Houston definitely took a risk wearing this modern white suit back in 1994. We love it and think it definitely works!
Whitney Houston
Mira Sorvino
Mira Sorvino won on and off the red carpet! She looks like a princess and also won the award for The Mighty Aphrodite.
Mira Sorvino
Reese Witherspoon
Reese looks classic in this vintage Christain Dior dress. She won the award for best actress for Walk the Line that evening.
Reese Witherspoon
Rita Moreno
This is the second time this elegant black and gold boatneck gown has hit the red carpet. Rita Moreno wore it for the first time in 1962 when she won the Oscar for Best Supporting Actress for her role in West Side Story. Fifty-six years later, she decided to rock the same look complete with beautiful black satin opera length gloves. We totally love this decision and this look. She looks amazing!
Rita Moreno
Nicole Kidman
At the 90th Academy Awards, Nicole Kidman looks like a total red carpet diva. We think she deserves a place on the year’s best dress list for her cobalt blue Armi Privé dress. The shape is so unique and it is tailored to perfection. We also love the bold red lipstick she chose to complement this look.
Nicole Kidman
Nicole Kidman
And again, Nicole Kidman wore this Balenciaga gown back in 2007. We love the bow draping from her neck. We think this dress really compliments her figure and the color is perfect for her skin and hair color. Nice job, Nicole!
Nicole Kidmans 2nd Look
Marion Cotillard
Marion Cotillard is just beautiful! In 2008 she turned heads wearing this Jean Paul Gaultier dress that looked as though it was literally made of fish scales. We think it is different and looks perfect on her!
Marion Cotillard
Zoe Saldana
Zoe Saldana at the 2010 Oscars was, well, interesting. She chose this Givenchy Haute Couture dress with a crystal embellished bodice and a big tulle train. We aren’t sure it is her best dress, but her makeup, hair, and accessories are great!
Zoe Saldanas 2nd Look
Michelle Williams
Back in 2010, Michelle Williams was nominated for Best Actress for My Week With Marilyn. She wore this cute red tulle Louis Vuitton gown. The matching lipstick is a beautiful touch.
Michelle Williams 2nd Look
Gwyneth Paltrow
Gwen wore this to the 2012 Awards. It is a beautiful Tom Ford cocktail dress. We approve!
Gwyneth Paltrow