The Oscars aren’t just the most prestigious awarding ceremony in acting history. It is also that one annual event where some of the biggest stars in the entertainment industry come dressed to the nines, captivating viewers and critics with exquisite designer pieces and jaw-dropping outfits. We’ve curated some of the looks that will go down as some of the most unforgettable outfits in Oscar history—either for their timelessness or being fashion faux pas.
Kendall Jenner
Kendall Jenner is easily a red carpet favorite. Much like how her family rarely makes mistakes in terms of money management, rarely does the supermodel ever make the mistake of donning a fashion no-no. While she may not have graced the red carpet for the Academy Awards itself, she is a staple figure at the after-parties, particularly the one hosted by Vanity Fair. This member of the Kardashian-Jenner brood is not one to shy away from sexy dresses that show a lot of skin and accentuate her assets, and she made a bold move when she wore a risqué Rami Kadi dress during the Vanity Fair Oscars after-party in 2019.
Miranda Kerr
Former Victoria’s Secret Angel Miranda Kerr is always a red carpet stunner. For the 2016 Vanity Fair Oscars after-party, she turned heads with a beautiful custom Kaufmanfranco dress, which came in a striking fire engine red color and featured cutouts that highlighted her toned figure. Much like Kendall’s dress, Miranda’s outfit leaves little to the imagination, but the supermodel carries it effortlessly and elegantly. To complete her look, Miranda wore a gold clutch bag from Swarovski, which also happens to be a company that provides insurance coverage for Swarovski Crystal collections. Her shoes for that night were from Christian Louboutin.
Hilary Swank
In 2005, it was a big year for Hilary Swank as her film “Million Dollar Baby” dominated that year’s awards season, bagging nominations from the Academy Awards, Golden Globe Awards, and Screen Actors Guild Awards. As for Hilary, she was highly favored to bring home the Best Actress Award, and when she stepped on to the Oscars red carpet, she appeared in an elegant gown from Guy Laroche fit for a winner. The beautiful sapphire piece was made with 27 yards of silk jersey, and it quickly became a favorite among fashion critics. Not only does Hilary have a solid acting credit, but she also cemented her place in the world of red carpet fashion.
Farrah Fawcett
Miranda Kerr and Kendall Jenner may be killing the red carpet nowadays with revealing looks, but back in the days, it was Farrah Fawcett who rocked that trend. In 1978, Farah stole everyone’s attention when she sashayed on to the red carpet wearing a gold Stephen Burrows gown. It was a simple dress that went on to become a timeless piece that inspired many red carpet looks of today and solidified Farrah’s status as a style icon. The “Charlie’s Angels” babe topped the look with her signature feathered blonde hair, which was popular on its own and even gave rise to the joke that her amazing her should be covered by insurance!
Grace Kelly
Grace Kelly, as her name suggests, will always be known as the epitome of grace and class. Before becoming Princess of Monaco through her marriage with Prince Rainier III in 1956, Grace was a stellar actress, having won an Oscar for her performance in “The Country Girl”. That night, she wore an ice-blue gown by Edith Head, which was made of French satin and was initially created to be worn for the film’s premiere. Since its red carpet debut, the dress has inspired many designers to recreate the look and give their own twist to it. Grace, without a doubt, will always be held up to a high degree of royalty in the world of acting, fashion, and real life.
Angelina Jolie
Through the years, Angelina Jolie has showcase growth and transformation on screen and the red carpet. Recently, Angelina has dressed in a more conservative manner for the red carpet, and among her most memorable outfits was the strapless black velvet gown from Atelier Versace, which she wore to the 2011 Oscars. The actress was not one to let anyone steal her red carpet thunder when she confidently walked the red carpet in a gown that featured a high slit that emphasized her long, toned legs. Clearly, if it’s a crime to look this good on the red carpet, a lawyer would be suing Angelina.
Andra Day
The fashion situation at the Oscars can be all sorts of things and many stars will arrive wearing shocking pieces. Andra Day’s look at the 2018 event was certainly something different from the sexy and sparkly looks most everyone else was wearing. With her floral pink and blue gown from Zac Posen, she definitely stood out from the others. She even gave everyone a lesson or two about being extra on the red carpet when she laid down the floor to pose for the cameras. If there’s a degree on how to do red carpet poses, Andra will surely ace it.
Sarah Jessica Parker
Sarah Jessica Parker has always lived up to her status as a fashion icon, serving the most exquisite looks on screen and the red carpet. The Christian Dior Haute Couture dress she wore at the 81st Academy Awards is definitely one for the books. The all-white number made the actress look like a dreamy princess from a fairy tale. Carrie Bradshaw in “Sexy and the City” may not have been the best at money management, as she lives a ridiculously lavish Upper East Side life outside of her means, but Sarah Jessica Parker definitely knows how to invest well in amazing couture pieces in real life.
Daryl Hannah
In 1988, Daryl Hannah brought back the popularity of the classic elbow-length gloves when she wore it together with her gold, figure-hugging cocktail dress to the Oscar Awards. Her overall vintage look made her seem like a dazzling star from Hollywood’s Golden Age, and it easily became one of the best Oscar red carpet looks of all time. Since then, many have come to recreate her look. She may no longer be visible in movies these days, but during her active years as an actress, she worked alongside big names such as Robert Redford in the film “Legal Eagles”, where Robert played a district attorney helping out Daryl’s character, who was accused of attempting to steal a painting from a millionaire.
Salma Hayek
Actress Salma Hayek made a huge statement at the 2008 Oscars when she appeared in a purple Gucci by Alessandro Michele gown. In the midst of all-black dress code for the night in honor of the Time’s Up and #MeToo movements, she added a pop of color to the event. Salma Hayek elevated her look with a ton of crystals, capping off her look with diamond chandelier earrings and a diamond ring by jeweler Harry Winston. Her jewelry alone amounted to a jaw-dropping $4.2 million, and we can only assume that her bling was covered by a good insurance plan.
Emily Ratajkowski
Emily Ratajkowski is a gorgeous woman, and she isn’t afraid of flaunting her assets. At the Vanity Fair Oscars after-party in 2016, Emily stunned the crowd in a sexy strapless black dress from Australian designer Steven Khalil. Her dress, a bustier bodysuit with a sheer lace skirting, may have been a bit simple compared to what the stars were wearing that night, but nevertheless, she turned heads and managed to look like a million dollars. The figure-flattering dress, to a certain degree, is a great mix of party-ready and red-carpet-ready. She also accessorized with a satin clutch bag from Tyler Alexandra.
Cindy Crawford
Supermodel Cindy Crawford is a beauty for the ages. Exuding both class, timelessness, and elegance, Cindy can don anything and still look regal. Cindy’s outfit to the 1991 Academy Awards took on a life and identity of its own. The red plunging dress earned public notoriety as the Red Versace dress of Cindy Crawford. The long evening dress was in stunning red color and featured a plunging neckline. The dress itself has since become a major game-changer in fashion, and it has earned a spot in many surveys as one of the greatest red carpet gowns of all time. Versace will also be known as a purveyor of statement pieces, and this red dress certainly adds to its credit.
Heidi Klum
Heidi Klum rarely ever makes a fashion miss, and her purple Marchesa dress at the 88th Academy Awards is certainly one of her most well-loved looks. Although her one-sleeved gown made her a standout in the Oscars red carpet that year, some fashion experts weren’t so keen on the look, with some noting that she looked like an out-of-place bridesmaid at the prestigious award-giving event. Love it or hate it, it was still a big night for Marchesa as many celebrities, such as Sofia Vergara and Chrissy Teigen, that night made investments to wear a gown from the said fashion house.
Celine Dion
Over the course of her decades-long career, Celine Dion has worn a lot of outfits that landed her in multiple best-dressed lists, but she certainly made a fashion statement when she appeared at the 1999 Academy Awards wearing a reversed white suit from Dior. She stepped up to the plate looking like the ultimate girl boss with a solid credit score, single-handedly serving a bold high-fashion look at one of the biggest nights in Hollywood. It was a ballsy move for the songstress to wear a white Christian Dior tuxedo backward and with a matching white fedora and diamond-studded Ray-Bans at that. As bizarre as it may seem, the look made a strong and lasting impression and remains to this day as one of the most memorable looks at the Oscars.
Cameron Diaz
Cameron Diaz has graced the Oscars red carpet several times, but it was in 2002 when she definitely landed in everyone’s favorite dress list. Digressing from the typical glamorous looks and sparkly designer pieces, the actress opted for a dress that was uniquely her. She stepped out in a floral-printed Emanuel Ungaro dress and utilized a 19th-century Indian necklace from Fred Leighton as a belt to elevate her look. It was different from what others were wearing, but it definitely left a good impression. Her look for that night can easily be recreated for any occasion without having to break one’s credit cards.
Demi Moore
Demi Moore’s look at the 1989 Academy Awards really turned heads for its uniqueness and the fact that it was designed by the actress herself. The Academy Awards red carpet isn’t the best place to perform a styling experiment and Demi’s look may have been described as bizarre at the time. Looking back, however, the actress may be considered a creative genius even without so much as a degree in fashion and design. She stepped out in a Renaissance-style corset with what looked like bike shorts. It was unconventional, to say the least, but right now is considered one of the coolest moments in Oscar red carpet history.
Cher
Quite simply, when it comes to Oscar red carpet fashion, nobody does it like Cher. Usually, it’s the best actress and best-supporting actresses that take the lead, but when Cher shows up, she shuts it down. Every decade, Cher always dons a look that will make everyone’s jaw drop. In 1986, the Academy asked the singer to present the award for Best Supporting Actor and she delivered. She arrived in a sparkly two-piece that showcased her toned torso. What made her look stand out more was the Bob Mackie headpiece she wore. Certainly, her bold choices always upped the electricity for the event.
Lady Gaga
Lady Gaga is known for pushing the boundaries and coming out with an element of surprise whenever she steps onto the red carpet. She delivered another surprise during the 2016 Oscars, but it was not what everyone was expecting. The singer-actress sported a white pantsuit, which was designed by her stylist Brandon Maxwell. The polished and elegant look had a stark difference from Gaga’s usual playful sartorial choices. That night, Lady Gaga was an absolute vision and exuded old Hollywood class. Interestingly, Brandon has evolved from being Lady Gaga’s stylist to putting his investment money into his own fashion line.
Juliette Binoche
The ‘90s was an interesting period for Academy Awards fashion. While there may be an Oscar award for Best Costume Design, red carpet outfits that seem like they were plucked out from a movie’s costume department are oftentimes frowned upon. Hence, Juliette Binoche had everyone’s eyebrows raised when she appeared in a brown velvet gown that made her look like she just arrived from the set of a fantasy-themed movie. Thankfully, her outfit did not have any effect on her acting credit and she still took home the Best Supporting Actress Award.
Kate Winslet
Kate Winslet is a prominent figure at the Oscars. Aside from being a repeat nominee, she also consistently appears on every best-dressed list whenever she makes an appearance. One of her most obsessed-over outfits was the red column dress she wore at the 2002 Oscars. The custom dress was designed by London-based designer Ben de Lisi. It was a simple yet classic piece that was telltale of Kate’s fashion preference. In a survey conducted by Debenhams and published in The Daily Telegraph, the dress ranked as the 7th greatest red carpet gown of all time, also catapulting Ben de Lisi to a high degree of fashion repute.
Elizabeth Hurley
Elizabeth Hurley was a strong force in the fashion world back in the ‘90s and was notoriously known for wearing one of the most controversial Versace dresses, now popularly referred to as the safety pin Versace dress. It was not a surprise that Elizabeth brought her A-game to the 1995 Oscars when she stepped out in a beautiful white gown, also from Versace. Although she was not a nominee at the time, she stole the show with the sparkling, curve-hugging outfit. Indeed, Elizabeth made good investments in iconic Versace pieces.
Cate Blanchett
Cate Blanchett is a known risk-taker in terms of red carpet fashion, and year after year at the Oscars, she always gets her sartorial choices right. In 2016, Cate served one of the most beautiful looks in Oscar history. Wearing a 3D floral Armani Prive gown, the actress looked like a beautiful and ethereal goddess. An abundance of floral detailing may be a hit or miss on the red carpet, but Cate’s Armani number got it just right. That year, Cate was nominated for her performance in the film “Carol” which sent a shock of electricity to film critics when it was omitted from the Best Picture and Best Director categories presumably due to the Academy’s indifference towards LGBT-centered films.
Lupita Nyong’o
Most celebrities don’t get their Oscar red carpet fashion moment right the first time, but that wasn’t the case for then-budding actress Lupita Nyong’o. Lupita stunned everyone when she wore this baby blue gown from Prada to the 2014 Oscars where she won Best Supporting Actress for her role in “12 Years a Slave”. The flowy dress, which features a low neckline, was an elegant piece fit for an Oscar awardee. In the movie, Lupita may have struggled with bankruptcy as slaves, but that night at the Oscars, she looked like a princess from a noble family in a fairytale.
Amanda Seyfried
Amanda Seyfried is another actress that doesn’t seem to get it wrong when it comes to her fashion choices. In 2013, it was a big year for the cast of “Les Miserables” as it stormed awarding ceremonies with multiple nominations. Amanda, although not receiving an acting nomination, came dressed like a winner in a beautiful Alexander McQueen gown. The dress, however, sparked a bit of a controversy for her co-star Anne Hathaway who revealed later on that she had to turn down wearing a Valentino gown for the Oscars because it looked similar to the one Amanda was wearing. Anne ended up winning Best Supporting Actress that night, adding to her already strong acting credit.
Amy Adams
As a six-time Academy Award-nominee, Amy Adams always got her Oscar red carpet looks on point. Her most notable outfit was her Oscar De La Renta gown at the 2013 Oscars where she was nominated for Best Actress for her role in “American Hustle”. The actress looked absolutely breathtaking in the dress, easily earning praise from fashion experts and viewers. Even if she does not have a degree in fashion, she co-designed the dress with Oscar himself. The vision for the dress was first conceived when Amy took photos and ideas to Oscar, and the fashion house worked hard to give Amy the dreamy and dramatic tulle-embellished piece.
Zendaya
At just 23 years old, Zendaya is already a force to be reckoned with. Her strong features and statuesque physique has made her a favorite muse among many designers and quite certainly one of the celebrities that many fashion critics look forward to on the red carpet. Zendaya made waves on the red carpet when she appeared at the 2015 Oscars red carpet wearing a sleek Vivienne Westwood gown and donning dreadlocks. Unfortunately, Guiliana Rancic, who is a “Fashion Police” host, remarked that the actress felt like she “smells of patchouli” or “weed”. She was immediately blasted for her racist remark, and this controversy led Zendaya to promote diversity in fashion. A year later, she also opened up about being racially profiled after using her credit cards to make a purchase at a grocery.
Faith Hill
Faith previously said in an interview that she likes to dress the way she feels. She must have been in such high spirits when she wore a multi-colored Versace number to the 2002 Oscars. Not a lot of people were fans of this look, and many pointed out that she looked like a colorful rainbow cake. Perhaps, at that time, the look was inspired by Faith’s bright and sunny Bahamas home, which is probably covered by a good home insurance policy. Nevertheless, her red carpet dress is still remembered by many to this day, although not for very nice reasons.
Kim Basinger
Here’s the thing – the Oscars can be a lot of things, including a melting pot of outrageous looks. Case in point, Kim Basinger’s 1990 Oscars dress was a white-hot mess, as described by many. Kim’s dress was trying to be too many things at once—at the top, it was a blazer and on the bottom part, it was a gigantic ball gown. Unfortunately, Kim only had herself to blame for this fashion disaster since she was the one who designed the dress. At that time, Kim was at the height of her success and many couldn’t believe that she had not been advised to make investments in quality outfits for the red carpet.
Whoopi Goldberg
Whoopi Goldberg is a well-loved comedian, but fans weren’t amused by her green and purple dress during the 1993 Oscars. The actress appeared like she just came out of a Disney movie with her costume-like ensemble. With a prolific career like hers, one would think she has a good credit score that is more than enough for her to get sound advice from a stylist. However, this was the ‘90s after all, a time when many were experimenting with different looks on the red carpet. Also, it’s forgivable because she’s Whoopi Goldberg and isn’t really keen on fashion.
Gwyneth Paltrow
The 71st Academy Awards was a memorable time for Gwyneth Paltrow for many different reasons. First, she bagged the Best Actress award, and second, she came in a beautiful bubblegum pink taffeta Ralph Lauren ballgown that went down in history as one of the best looks seen on the Oscar red carpet. She was decked in jewelry comprising of $160,000 worth of Harry Winston diamonds, from her bracelet to her choker and earrings—all of which was covered by an insurance package. The overall look packed a punch and catapulted Gwyneth to becoming one of Hollywood’s most reputable actresses and notable style icons.
Kate Hudson
Kate Hudson is definitely known for her classy and glamorous style, which she probably got from her mother, actress Goldie Hawn. One of her strongest red carpet looks was the one she wore at the 2003 Oscars. The pale Versace number was a timeless, classic piece, and it perfectly fits Kate’s regal look. The Academy-Award nominee has since been a favorite of fashion critics for being consistent with her good taste in clothing on the red carpet. Because of her love for fashion, she spent a good amount of her investment money into building her own clothing line for women named HappyxNature.
Michelle Williams
It’s rare to see actresses don a pop of color in the Oscars red carpet. A solid yellow color is particularly very challenging to pull off if not done correctly. However, Michelle Williams nailed the bright look effortlessly when she graced the 2006 Academy Awards red carpet in a saffron yellow piece from Vera Wang. It is often listed as one of the best Oscar dresses of all time. The yellow gown made Michelle glow even more. Coupled with bright red lips, the actress looked like a vision from an old Hollywood film. If this look is equated with a credit report, it would be flawless.
Octavia Spencer
Octavia Spencer is a renowned actress and one with exquisite fashion taste. She is one to wear dresses that perfectly accentuate her curves, such as her 2012 Academy Awards look which was designed by Tadashi Shoji. Octavia wasn’t just a winner on the red carpet, but also during the actual awarding ceremony when she received Best Support Actress for her role in “The Help”. She was a favorite to win the said award, following her victory at the Golden Globes. Octavia’s character in “The Help” may have been ridden with financial problems including mortgage, but that night of the Oscars, Octavia looked like Hollywood’s brightest star.
Marion Cotillard
Marion Cotillard is arguably one of the most beautiful actresses in recent times. At every red carpet event, she fails to disappoint. One of her best looks was during the 2008 Academy Awards where she wore a stunning ivory mermaid dress from Jean Paul Gaultier that perfectly accentuated her figure. The dress was embellished with shimmering scales making her look like a star for the ages. That night, she received an award for her performance in the Edith Piaf biopic “La Vie En Rose”, for which she garnered worldwide acclaim. However, the actress previously stirred a controversy when she questioned the accuracy of the 1969 Moon Landing and argued that it’s unlikely planes could bring down the Twin Towers. Her lawyer said that the actress did not intend to contest the said events.
Zoe Saldana
Zoe Saldana rose to Hollywood prominence after portraying intergalactic characters with brightly-colored skin tones, but in real life, there is no color Zoe can’t pull off on the red carpet. The actress turned heads when she popped out in the red carpet in a Givenchy Haute Couture gown that featured an embellished bodice and tulle ruffled skirt. The ombre hues on the bottom of the dress added character to an already stunning piece of art. While most stars opted for safer looks that night, Zoe broke the mold and chose this bold number. It looks like the perfect dress for a powerhouse actress with a good credit rating.
Meryl Streep
The Academy Awards would be incomplete without a Meryl Streep sighting. Surely, this veteran actress has been a staple figure at the awarding ceremony for years. Although she is already 70 years old, she never fails to keep on serving timeless looks on the red carpet. Her sartorial choices are as diverse and versatile as her acting range. She made a huge statement when she arrived in a gold Lanvin dress fitting for a golden girl like her! After decades of appearing at Hollywood’s most anticipated event, she is still as consistent as ever. Thankfully, she has used her credit cards on getting the best team of stylists and hair and makeup artists to up her look every year.
Halle Berry
An Oscar Best-Dressed List would not be complete without Halle Berry’s outfit during the 2002 Academy Awards. The Elie Saab net dress is one for the books and is regarded by many as one of the best red carpet gowns of all time. Not only that, but it is also one of the most recognized Oscar outfits of all time. Halle certainly made history that night, not just with her dress but also with her Best Actress win for the film “Monster’s Ball”. Her victory made her the first and only woman of color to bag the Best Actress title. Halle’s win was hoped to open more chances for actresses of color to be held to the same degree as white actresses with respect to getting Oscar recognition.
Bjork
Again, having one of the most unforgettable looks of all the time can be a good thing or a bad thing, and for singer Bjork, it’s the latter. The Icelandic singer wore a swan dress to the 2001 Academy Awards. Although she is known for her eccentric style, many thought her choice was inappropriate for the event. Nevertheless, Bjork’s odd yet bold move is still regarded by fashion experts as one of the most iconic red carpet looks of all time. Bjork remained unfazed by the hype surrounding the dress, commenting, “It’s just a dress.” Years later, a Ukrainian prankster crashed the 2013 Oscars ceremony wearing a swan dress inspired by Bjork’s despite receiving a letter from the Academy lawyer prohibiting him from hatching his plan.
Julia Roberts
Julia Roberts has had many memorable Academy Awards looks over the course of her career, but perhaps the one most favored and obsessed-over by many was the Valentino gown she wore during the 2001 ceremony. That time, Julia received the Best Actress Award (it was her first Oscars) for her role in “Erin Brockovich”, wherein she portrayed the eponymous legal clerk, who despite not having a formal law degree, was instrumental in winning the landmark case against Pacific Gas and Electric Company in 1993. According to the actress, the black and white number Julia won that night is still kept in her home.
Jennifer Lopez
Jennifer Lopez served this romantic Elie Saab gown at the 2015 Oscars Red Carpet. The blush-colored embellished beaded gown boasted a plunging deep-V neckline and form-hugging silhouette. The multi-hyphenated star is a strong force both in the acting and music industry, and she’s also highly respected in the world of fashion. As a matter of fact, she spent a huge chunk of her investment money in building her own brand named J.Lo, which carries fragrances and clothing for women. The clothing line, however, was heavily criticized by animal rights groups for frequently using animal fur in many of its designs.
Penelope Cruz
Penelope Cruz is another actress that is considered by many as a darling on the red carpet. One of her most memorable Oscar red carpet moments was in 2007 when she stepped out in a blush-colored Versace gown. The strapless number featured a silk chiffon bodice and a beautiful train that consisted of silk chiffon, organza, and tulle. Without a doubt, Penelope’s selection of feminine pieces is always something viewers look forward to seeing. Penelope turned her love for fashion into a noble cause. Last year, she made investments on a joint venture with Atelier Swarovski to come up with a line of ethically-sourced jewelry.
Jennifer Lawrence
Academy Award-winning actress Jennifer Lawrence has had a lot of moments at the Oscars, like that one time when she tripped on the stairs on her way to receive her Best Actress award for her performance in “Silver Linings Playbook”. But Jennifer’s funny antics are one thing, and her fashion statement is another. Her first Oscars appearance was perhaps one of the most memorable. She wore a simple scarlet Calvin Klein dress that accentuated her figure and gave her a fresh, youthful glow. Since then, her red carpet choices have evolved into more intricate pieces, especially now that she no longer has to worry about maxing out her credit cards buying couture dresses for her red carpet stints.
Charlize Theron
Charlize Theron has been an Oscars red carpet staple since her Best Actress win for “Monster” in 2004. Whether she’s presenting or among the contenders for an award, Charlize never fails to put her best foot forward on the red carpet. At the 2019 Oscars red carpet, she surprised everyone with a new look—a brunette bob. Her new hairstyle perfectly matched her periwinkle Dior turtleneck with a sexy open back. Before this, she’s had many other iconic looks—including her red Dior Haute Couture dress with a plunging neckline. With an acting credit as hers, it’s no question that she also has exquisite taste in fashion.
Madonna
Madonna channeled Marily Monroe in the beautiful all-white ensemble she wore at the 63rd Academy Awards in 1991. She wore a sparkly figure-flattering piece from Bob Mackie and $20 million worth of Harry Winston diamonds. With that much bling on her, one can ascertain that it was covered by a secure insurance policy before it landed in Madonna’s hands. Madonna also coordinates her look with Michael Jackson’s overall getup, who was her date for that night. Together, the duo looked like the power couple of everyone’s dreams and combining their net worth, the amount is probably as sparkly and shimmering as the outfits they wore together.
Mira Sorvino
Mira Sorvino looked like an elegant princess when she appeared at the 1995 Oscars red carpet. Her look was fit for a winner, as she emerged victorious in the Best Supporting Actress category for her role in “Might Aphrodite”. She dedicated her win to her father, whom she said taught her everything she knew about acting. Years later, Mira became one of the actresses that fought against sexual misconduct in Hollywood, revealing that she was also a victim before. Aside from being a decorated actress and activist, she was also a star student when she was young. She graduated magna cum laude from Harvard with a degree in East Asian studies.
Reese Witherspoon
Reese Witherspoon started her career as a young teen star. Thus, you can imagine that her red carpet looks have evolved since her first public appearance. One of her most memorable looks was during the 2006 Oscar red carpet, where she wore a vintage Christian Dior dress from the 1950s. That night, Reese also received the award for Best Actress for her role in “Walk the Line”. As a top actress with a good credit score, it wasn’t difficult for Reese to score this Dior stunner from a Parisian vintage boutique. It is said that this gown was once owned by royalty.
Rita Moreno
Repeating outfits to the Oscar red carpet is almost unheard of, but actress Rita Moreno has done it. Rita first wore this elegant black and gold gown in 1962 when she won an Academy Award for Best Supporting Actress for her role in “West Side Story”. Decades later, she decided to reuse the dress, but this time adding a pair of black satin opera length gloves as an accent. The dress still looks as good as it was when she first wore it. With a lengthy acting career spanning decades, Rita has devoted her time helping out budding actors and actresses by funding various scholarships that cover student loans.
Nicole Kidman
At this point in her career, Nicole Kidman has already solidified her place as a fashion red carpet favorite. At the 90th Academy Awards, she delivered another stunner when she appeared wearing a cobalt blue dress from Armani Prive. The shape and the color of the dress are so unique that it made the Australian babe stand out on the red carpet. Although her style has changed over the years, she never fails to wow everyone. Certainly, her infamous divorce from Tom Cruise did not affect her credit at all, and she remains to be one of the most renowned actresses of recent times.
Jennifer Aniston
Jennifer Aniston doesn’t always wear a red dress, but when she does, she’s an absolute stunner! She’s served amazing red carpet looks over the decade, but this is one for the books. She wore a strapless crimson Valentino Haute Couture gown at the 2013 Oscars that had fashion experts craving for more. The striking red color made Jennifer glow even though her hair was kept down naturally. Rachel Green may have maxed out all of her credit cards at one point in the hit TV series “F.R.I.E.N.D.S”, but Jennifer has managed to look just as good as her television character without breaking the bank!
Barbara Streisand
Barbara Streisand broke the mold when she appeared in the 1969 Oscar Awards wearing an Arnold Scaasi bell-bottomed pantsuit. While everyone else was donning glamorous and intricate gowns, Barbara went for the road less taken and opted for a sheer pantsuit. That night she won the Best Actress award for her role in “Funny Girl”, and she even made that year at the Oscars more memorable for her when she tripped on her way up the stage to receive her award. Barbara is already retired as an actress and singer, but nevertheless, she still lives comfortably in massive mansions that are probably protected by high-end home security systems.
Faye Dunaway
These days, the red carpet is dominated by young stars such as Jennifer Lawrence, Lupita Nyong’o, to name a few. Back in the day, Faye Dunaway was among the stars that were most anticipated on the red carpet during her prime. For the 1968 Oscars, Faye rocked a black ruffled wrap dress, which was created by Theodora Van Runkle, one of Hollywood’s biggest names in costume designing. At that time, Faye was nominated for an Oscar for her role in “Bonnie and Clyde”. She may have played an outlaw in the film running with a gas station attendant, a preacher’s daughter, and her lover, but she certainly exuded class in this dress.
Lola Falana
When it comes to rocking a feathered boa on a formal event, fashionistas have a thing or two to learn from actress Lola Falana. In 1970, Lola added a touch of drama to her classic black gown by wearing an all-white feather boa. Before Lola suffered from multiple sclerosis in 1987, through which her healthcare insurance may have come in most handy, the actress enjoyed a prolific acting career in Italian cinema. She later became familiar to American TV audience for her work on “The Joey Bishop Show” and “The Hollywood Palace”.
Lauren Hutton
Effortless, chic, and glamorous—that was the statement Lauren Hutton was trying to make when she stepped out in a plunging rainbow Halston gown and accessorized it which a large fur jacket. Nothing screamed like 1970s Hollywood glam quite like the outfit Lauren was wearing that night. Aside from being a successful actress, she also enjoyed a very lucrative modeling career. To this day, she continues to appear in various campaigns for fashion brands such as H&M and Alexander Wang. Thanks to her successful career, Lauren probably still maintains a good credit score even though her late husband squandered a huge portion of her wealth.
Debbie Allen
Bold and structured shoulders are all the rage right now in fashion. Back in the day, it was Debbie Allen who dominated the ‘80s fashion world, and she brought her A-game wearing an embellished gown with a thigh-high slit and structured shoulders. To highlight the gown’s high neckline, Debbie wore her curly hair in a cool updo. Not only is Debbie a great model and actress, but she is also very well-rounded. She finished her bachelor of arts degree in classic Greek literature, speech, and theater from Howard University. Debbie was also a member of President George W. Bush’s President’s Committee on the Arts and Humanities.
Diana Ross
Multi-awarded star Diana Ross captivated everyone’s heart when she rendered a powerful rendition of “Endless Love” at the 1982 Oscars with Lionel Richie. But before her big performance, she turned heads at the red carpet when she wore a striking red sequin own on the red carpet. The gown featured intricate detailing and a vertical cut out along the chest area. She also topped off the look with a white fur over one shoulder. While she lived a glamorous life, she also remained grounded and humble. She even sponsors various scholarships under her name to help students pay for their student loans.
Winona Ryder
A woman can never go wrong with a classic black dress and such was the case for Winona Ryder. Then a budding actress, Winona stole the show when she appeared in a figure-flattering strapless black gown for the 1990 Oscars. The dress featured a low neckline, and she looked like a classic beauty with her hair tied in a neat bun. Years later, Winona almost faced bankruptcy after she was caught stealing $5,500 worth of merchandise from Saks and was also caught in possession of prescription drugs. She made a huge comeback in recent years through the hit Netflix series “Stranger Things”.
Sharon Stone
In a recent interview, actress Sharon Stone opened up about how she was constantly body-shamed when she was in her 20s. However, when she graced the red carpet of the 1998 Oscars, she was every bit the strong and confident woman that she is. Contradicting the highly-bedazzled outfits that frequented the red carpet that night, Sharon opted for a low key lavender satin Vera Wang skirt and a white button-down shirt that she didn’t button up completely. She also kept her accessories to a bare minimum, wearing only a diamond bangle like most jewelry that appears in the red carpet, which is also covered by insurance.
Renee Zellweger
Renee Zellweger was nominated for playing the bright and sunny lead character in the film “Bridget Jones’s Diary”. On the red carpet of the 2001 Oscars, she was also as bright and sunny as her role. She wore a yellow vintage Jean Desses strapless gown, which showcased her svelte figure. She wore her golden locks in curls and red lipstick for a timeless, elegant look. In the film, Renee may have been the awkward girl who fell in love with a human rights lawyer portrayed by British actor Colin Firth, but on the red carpet, she looked very dazzling and radiant.
Mila Kunis
In 2011, everyone was talking about the critically-acclaimed film “The Black Swan”. It stirred controversy, but for good reasons. Even on the Oscars red carpet, the film’s stars were much-talked-about. Mila Kunis, in particular, generated a huge buzz that night when she hit the Academy Awards wearing a lavender chiffon gown from Elie Saab. Fashion experts raved about the dress’s soft and romantic look. That year, a lot of high school students looked up to Mila’s dress as inspiration for their prom looks and the dress spawned a lot of similar-looking pieces that wouldn’t make parents go bankrupt.
Anne Hathaway
Every time Anne Hathaway makes a red carpet appearance at the Oscars, all eyes are always on her. The actress is a frequent item in a lot of best-dressed lists and is a favorite among designers and fashion stylists. At the 2009 Oscars, Anne looked absolutely stunning and radiant in an Armani Prive gown that was covered in opal paillette. At that time, she was nominated for her role in “Rachel Getting Married”. To put the spotlight on her dress, Anne kept her insurance-covered accessories subtle. If the films that are honored at the Oscars are considered works of art, we could say the same for Anne’s overall look.
Susan Sarandon
The ‘90s were a peculiar time for Oscars fashion and many celebs were huge on experimenting and going all out with expressing themselves sartorially. One of those stars that defied that odds was Susan Sarandon. Her massive bronze-colored ball gown designed by Dolce and Gabbana may have looked like it was something from a Victorian film’s costume department, but it was every bit apt for the night’s formal black tie dress code. She looked like a rockstar wearing sunglasses on the red carpet, too. The dress, which was a flawless mix of vintage and modern, sparked electricity in the air that night.
Rooney Mara
Like Jennifer Lawrence, Rooney Mara also made a strong debut at the Oscars red carpet wearing a Givenchy Haute Couture gown. At the 2012 Academy Awards, she was nominated for her role in “The Girl with the Dragon Tattoo” and her look that night was definitely tattooed on everyone’s mind. Like her character, Rooney is also quite a badass in real life as well. She holds a bachelor of arts degree from New York University’s Gallatin School of Individualized Study. She also has a solid vocal prowess and once dreamed of performing for a musical on Broadway as she grew up watching a lot of musicals as a young kid.
Viola Davis
Viola Davis is a powerful actress, and the outfits she wears on the red carpet are also at the same level. She isn’t one to shy away from wearing bright colors on the Oscar red carpet, but her gold Reem Acra gown during the 2009 Oscars definitely pops out among the many. The gold dress perfectly accentuated the star’s toned figure, and the color looks great on her skin tone. Viola plays a tough lawyer and professor on “How To Get Away With Murder”, and even on the red carpet she can never commit a fashion crime!
Jessica Chastain
When it comes to a re-emergence of the old Hollywood glam look in recent red carpet history, you can trust that Jessica Chastain is at the forefront of it. At the 2013 red carpet, Jessica looked like a huge star from Hollywood’s Golden Age when she appeared in an embellished gold Armani Prive gown with a sweetheart neckline. Her red locks were kept in soft waves, and she completed her look with bright red lipstick for that classic look. Jessica is one of the most respected actresses in recent times, owing much of her acting to her Juilliard School education, where she graduated with a degree in Fine Arts.
Natalie Portman
Natalie Portman looked like a Greek goddess when she appeared at the 2005 Oscars. The sheer number was designed by Lanvin and was beautifully paired with bronze-colored belts and a clutch bag from Tiffany & Co. She wore it with such great composure and confidence that it was no question when she immediately grabbed everyone’s attention the moment she sashayed onto the red carpet. She may have lost the Best Supporting Actress Award to Cate Blanchett, but she still looked like a winner. Natalie already has a solid acting credit to her name, and so does her fashion track record.
Saoirse Ronan
Saoirse Ronan may be one of the younger actresses on this list, but when it comes to her fashion choices, she can definitely compete in the big leagues. Saoirse opted for an age-appropriate dress at the 2018 Oscars, wearing a pink Calvin Klein dress with a huge bow detail at the back. At that time, Saoirse was only 23 years old, but she was already listing her third Oscars nomination. The couture-level piece looks fun and high-fashion and immediately became noted as one of the most iconic dresses to hit the red carpet. Despite her level of fame, Saoirse admitted that she regrets missing out on school life due to her career. However, she probably doesn’t miss being swamped in student loans.
Emma Stone
Like most everyone on this list, Emma Stone has graced the Oscars red carpet several times already. It’s almost too difficult to pick out her best look because she looks great year after year. However, she will probably be most remembered for her 2017 Academy Awards appearance. That night, Emma stepped out in a gold Givenchy Haute Couture which made her exude timeless old Hollywood class. The gown, due to its fine detailing, took a jaw-dropping 1,700 hours to create. It was definitely a dress made for a winner as Emma that night took home the award for Best Actress for her role in the critically-acclaimed “La La Land”. Through this look, Emma also showed her support for family health insurance by wearing a Planned Parenthood pin.
Billy Porter
With the rise of overwhelming support for LGBTQ+ rise, Billy Porter took charge of the moment by wearing a gender-bending look with a Christian Siriano gown that was a mix of a tuxedo at the top and a ball gown at the bottom. While mixes and matches don’t often sit well on the red carpet, Billy nailed it and he quickly stole the limelight that night when he stepped onto the Oscars red carpet. Billy is known to make political statements through fashion, and this one definitely had everyone talking. This iconic look added more credit to Billy’s name.
Gemma Chan
Gemma Chan played an immensely wealthy Asian heir with great money management skills in “Crazy Rich Asians”, and she looked as rich as her character when she appeared in a voluminous pink Valentino Haute Couture dress at the 2019 Oscars. She completed her look with a pair of shoes from Jimmy Choo and jewelry from Bulgari. The dress was unlike anything seen before on the red carpet of the Academy Awards—it was bright, fun, and innovative. It was definitely one for the books and made everyone go ‘Wow!’. Gemma really lived up to her character as the powerful Astrid in the movie.
Jennifer Lawrence
Jennifer Lawrence, despite her crazy antics on the red carpet, is always admired for her sartorial choices. Rarely does this girl ever go wrong with what she wears during the Oscars, and her Dior lace gown at the 2016 Oscars definitely had everyone going gaga. The sexy look, which was a mix of both lace and tulle, was proof of Jennifer’s constantly evolving fashion sense as well as her growing acting portfolio, this time with the addition of “Joy” to her acting acclaim. If she constantly drops investment money on amazing Dior pieces, Jennifer will land on everyone’s best-dressed list year after year.
Keira Knightley
Some stylists tend to tone down celebrities’ accessories to make their outfits pop out even more on the red carpet. But who says you can’t rock a gorgeous dress and wear a stunning piece of jewelry at the same time? Keira Knightley did both when she wore a beautiful plum Vera Wang gown to the 2006 Oscars and grabbed everyone’s attention, not just for her dress but also for her Bulgari bib necklace. She broke every style rule, but she managed to still look like a masterpiece! The necklace came from an Italian jewelry collection from the 1960s. Stunning jewelry like that must have been covered by a really good insurance policy.