Awards season is back, and the jewel in its crownâthe Oscarsâis upon us. Sure, most of us night spend our days in sweatpants and jeans, but weâre looking forward to the sartorial escapism that the Oscars red carpet will bring this year. Since 1929, the Academy Awards has maintained firm footing in the zeitgeist not only by being a point of contention and conversation but also for history-making moments, including some of the best red carpet looks of all time. While some years are more memorable than others, we prefer to focus on the standout moments that made us smile. Sequins, satin, and sleeveless dresses may be timeless, but the best Oscars looks of all time arenât always the safest betâtheyâre daring, bold, and sometimes deemed âthe worstâ at first, but thatâs what makes them iconic. Ahead, youâll find the 49 Oscars looks that surprise and delight and that were truly indicative of the times.
WHO: Audrey Hepburn and Jean Hersholt. WHAT: 1954 Academy Awards  . WEAR: On Audrey Hepburn: Givenchy gown . Oscars night 1954 was a major moment for Audrey Hepburnânot only did she win the Best Actress award for her breakout role in Roman Holiday, but itâs also worth noting that her custom-made Givenchy gown ushered in a new era in fashion. Hailed as one of the most classic dresses of the 20th century, this dress was indicative of Hepburnâs role as muse to French designer Hubert de Givenchy, and their relationship went on to change the way celebrities and designers worked together.
WHO: Grace Kelly and Edmond O’Brien. WHAT: 1955 Academy Awards. WEAR: On Grace Kelly: Edith Head gown and coat. It doesnât get more glamorous than the future princess of Monaco, award-winning actress Grace Kelly. While she served quite a few iconic looks on- and off-screen, her custom-made Edith Head gown was her most iconic red carpet outfit for several reasons: That night, she took home the award for Best Actress (in the film The Country Girl), and it was one of the most expensive dresses worn to the ceremony, crafted from ÂŁ3500 worth of French satin.
WHO: Elizabeth Taylor. WHAT: 1957 Academy Awards  . WEAR: William Ruser tiara and earrings. Yes, gowns are an essential part of making the Oscars a true Hollywood affair, but letâs be honest: The jewellery really makes the night sparkle. No one quite knew the power of jewels like actress Elizabeth Taylor. After all, who else could pull off wearing a full-diamond tiara to the Academy Awards?
WHO: Barbra Streisand. WHAT: 1969 Academy Awards. WEAR: Arnold Scaasi jumpsuit. Long before naked dresses and sheer jumpsuits were a thing, Barbra Streisand turned heads with her transparent jumpsuit at the 1969 Academy Awards. Of course, the subtly sheer number was enhanced by the spotlights, but Streisand’s star powerâincluding taking home her first statue that nightâwas anything but accidental.Â
WHO: Cher and Sonny Bono . WHAT: 1973 Academy Awards . WEAR: On Cher: Bob Mackie two-piece gown. Any Cher fan knows that sheâs spent the duration of her career serving up iconic looks (she pioneered the naked-dress trend), but none are seared into our brains quite like her 1973 Oscars look. This stunning sequinned two-piece Bob Mackie gown is the stuff of psychedelic â70s dreamsânot to mention, she looks fantastic. Cher, please drop the core workout routine.
WHO: Farrah Fawcett and Marcello Mastroianni . WHAT: 1978 Academy Awards . WEAR: On Farrah Fawcett: Stephen Burrows gown . Farrah Fawcettâs slinky, gold Stephen Burrows gown rivals an Oscar statue itself.
WHO: Diana Ross and Ernest Thompson . WHAT: 1982 Academy Awards. WEAR: On Diana Ross: red sequin gown; white fur stole  . If youâre coming out to the Oscars, you want to go all the way out. In the â80s, no one quite brought the glamour like singer and actress Diana Ross. This head-to-toe red sequinned gown is everything.
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WHO: Whoopi Goldberg. WHAT: 1991 Academy Awards . WEAR: black sequin column dress; pearl necklace and earrings. There are very few artists in the world who have won an EGOTâWhoppi Goldberg is one of them. Goldberg is the first-ever African American to be nominated for Best Actress and Best Supporting Actress (which she won in â91 for her performance in Ghost). Her look for the 1991 Academy Awards encompassed the type of popular sequinned column dresses that were everywhere during the late â80s and early â90s, making it historic in and of itself.
WHO: Madonna and Michael Jackson. WHAT: 1991 Academy Awards . WEAR: On Madonna: Bob Mackie gown; Harry Winston diamond necklace and earrings . Sooner or later, when it comes to rounding up a list of iconic red carpet looks, you have to include Madonna. Her â91 Oscars outfit was one for the history books, as she channeled Marilyn Monroe with a sequinned sweetheart-neckline Bob Mackie gown and ÂŁ18 million worth of Harry Winston jewellery. Material girls, this is your look.
WHO: Sarah Jessica Parker and Matthew Broderick . WHAT: 1993 Academy Awards . WEAR: On Sarah Jessica Parker: brown sequin gown; blue-lens sunglasses . Donât get it twisted. Long before serving iconic on-screen looks as Carrie Bradshaw in Sex and the City, Sarah Jessica Parker was giving us head-to-toe âfits. Case in point: the simple yet very â90s brown sequin gown and blue-lens sunglasses she wore to the Academy Awards in 1993.Â
WHO: Vanessa L. Williams . WHAT: 1995 Academy Awards . WEAR: sequin and mesh gown; pashmina; clutch bag. Remember the chocolate-brown, sequin, and mesh number Vanessa L. Williams wore in â95? The gownâwith its multiple fabrics, colour, and cutâwas far ahead of its time and includes almost every â90s trend we hold dear today.
WHO: Naomi Campbell. WHAT: 1996 Academy Awards. WEAR: yellow gown; diamond choker. Honestly, is it even a roundup of the best red carpet looks of all time without Naomi Campbell? Whatâs great about her 1996 Oscars look is the sheer understated elegance of itâthe yellow floor-length gown with the halter cut paired with a diamond choker necklace is just too good for words.
WHO: Nicole Kidman and Tom Cruise . WHAT: 1997 Academy Awards . WEAR: On Nicole Kidman: Christian Dior Couture gown. When we think of the Oscars today, we think of couture, but that wasnât the standard in 1997. Nicole Kidmanâs stunning yellow Christian Dior Couture gown put newly appointed John Galliano on the map and couture on the carpet, elevating both the fashion industryâs profile in Hollywood and the Oscars red carpet for years to come.
WHO: Gwyneth Paltrow. WHAT: 1999 Academy Awards . WEAR: Ralph Lauren ball gown; Harry Winston diamond necklace and earrings . At the time of their debuts on the carpet, many of the most iconic Oscar looks were met with either fanfare or outright disgust. For Gwyneth Paltrowâs 1999 bubblegum-pink Ralph Lauren gown with ÂŁ140,000 worth of Harry Winston diamonds, it was the latter. Why anyone wouldnât love this look, weâre not sure, but does it matter? She took home the Best Actress award for her role in Shakespeare in Love and served one of the most remembered looks to date.
WHO: Celine Dion. WHAT: 1999 Academy Awards . WEAR: Dior suit; fedora; diamond-studded Ray-Bans. The fashion critics in â99 were particularly harsh on Oscars red carpet looks, including Celine Dionâs white Dior satin pantsuit by John Galliano, which she wore styled backward. Little did they know, this would become one of her most iconic looks ever and one of the most-celebrated Academy Awards looks of all time. Guess it pays to think outside the box (or just to be Celine Dion).
WHO: Uma Thurman. WHAT: 1999 Academy Awards. WEAR: Chanel two-piecedress; bangle bicep cuffs . Something must have been in the water at the 1999 Academy Awards because it served us some serious looks, particularly this two-piece Chanel outfit from Uma Thurman. Of course, it wasnât her first time stealing the red carpet (she championed a silk lavender Prada dress in â94), but itâs an outfit that has left many in their feelings.
WHO: Salma Hayek . WHAT: 2000 Academy Awards. WEAR: Eric Gaskins gown. Salma Hayek has donned some of the chicest Oscars red carpet looks over the years, but none are quite as lovely as her â00s ceremony gown. The lavender, beaded Eric Gaskins gown with a deep V-neck may not be the most exuberant dress ever worn on the red carpet, but its subtle elegance is what makes it worthy of being considered one of the best Oscars looks of all time.Â
WHO: Lucy Liu. WHAT: 2000 Academy Awards. WEAR: Versace dress . As editors, weâre always delighted when we come across a resurging trend or a forgotten incredible red carpet lookâthat is the case with Lucy Liuâs â00s Oscars ensemble. The stunning red and black, one-shoulder Versace gown needs to be brought back into the cultural psyche because itâs just too good.
WHO: Jennifer Aniston and Brad Pitt . WHAT: 2000 Academy Awards. WEAR: On Jennifer Aniston: Atelier Versace gown. The black dress is not a new concept to the red carpet, but no one can quite wear a deep V-neck black gown like Jennifer Aniston. Since her attendance at the â00s Academy Awards in Atelier Versace, sheâs championed this cut time and again, but can you blame her? A dress this good deserves to be seen.
WHO: Halle Berry. WHAT: 2002 Academy Awards. WEAR: Elie Saab gown. There are numerous reasons why Halle Berryâs 2002 Oscars look can be considered one of the best of all time. Her half-sheer embroidered gown not only put Elie Saab on the map, but she also became the first Black woman to win Best Actressâtalk about iconic.
WHO: Kate Hudson. WHAT: 2003 Academy Awards. WEAR: Atelier Versace gown. Encapsulating Hollywood glamour into a singular gown isnât easy, but thatâs precisely what Donatella Versace did with the stunning floor-length gold gown worn by Kate Hudson in â03. Every detail, from the hand-sewn embroidery to the 14k gold lining, on the effervescent Hudson makes this look worthy of its own award.
WHO: Charlize Theron . WHAT: 2004 Academy Awards. WEAR: Gucci gown . Charlize Theronâs performance in the film Monster isnât the only thing worthy of an Oscar. Her red carpet look for the â04 ceremony is, too. Tom Ford designed the stunning strappy, bedazzled Gucci gown, and the pairing of Theronâs wavy hairdo and bleached eyebrows makes this a look we canât forget.
WHO: Oprah Winfrey and Hilary Swank. WHAT: 2005 Academy Awards. WEAR: On Oprah Winfrey: Vera Wang gown; On Hilary Swank: Guy Laroche dress. What makes the Oscars red carpet unique is that the ensembles range from classic to cutting-edge at every ceremony. The two looks that distill the full scope of Oscarâs style are what Oprah Winfrey and Hilary Swank wore to the 2005 ceremony. Winfrey opted for a classic, fitted Vera Wang gown, while Swank donned a floor-length, open-back navy gown by Guy Laroche. The result? Two incredible women in two iconic looks that are worth thinking about.Â
WHO: Reese Witherspoon. WHAT: 2006 Academy Awards. WEAR: vintage Christian Dior gown. Reese Witherspoonâs â06 Oscars gown may be considered traditional by most, but what makes this Dior dress immaculate is that this champagne-coloured beaded gown was found by her stylist in a vintage store in Paris. C’est magnifique.
WHO: Penelope Cruz. WHAT: 2007 Academy Awards. WEAR: Atelier Versace gown. I have yet to see an Atelier Versace red carpet look I did not loveâPenelope Cruzâs â07 Oscar Awards ensemble is high up there for me. Whatâs fantastic about this look is that the pale-pink strapless gown has this stunning ruched bodice and full feather skirt, making it a dreamy, princess-like look that could only be embodied by Cruz herself.
WHO: Angelina Jolie . WHAT: 2009 Academy Awards. WEAR: Elie Saab gown; emerald earrings . My love for Angelina Jolie was cemented by her 2009 Oscars red carpet look. While some critics may consider the 2012 black high-slit Atelier Versace gown her best look of all time, Iâll go to bat for this look. Yes, the Elie Saab gown stole my heart, but Jolieâs stunning emerald earrings are what sealed the dealâthe dramatic colour contrast, the size, and her damn cheekbones just make this look too divine for humanity.
WHO: Rooney Mara. WHAT: 2012 Academy Awards. WEAR: Givenchy Couture. While Rooney Maraâs red carpet style may appear to be simple from far away, the intricate details, textures, and fit say otherwise. Take, for example, her 2012 Oscars red carpet look. To the objective on-looker, sheâs wearing a simple white gown, but for the fashion crowd, we know that this Givenchy couture was custom-made by Riccardo Tisci with pearl-coloured lace.
WHO: Meryl Streep. WHAT: 2012 Academy Awards. WEAR: Lanvin gown and belt; Salvatore Ferragamo shoes. Meryl Streep stirred up the whole pot at the 2012 Academy Awardsâand not just because she won Best Actress for her performance as Margaret Thatcher in The Iron Lady. Her choice of Lanvin garnered considerable discussion among the industry not just because people were unsure about the full-gold look but also because Streep selected Lanvin over Chanel for the ceremony. No matter what the tea is, this look is one weâll be talking about for years to come.
WHO: Jennifer Lawerence and Anne Hathaway. WHAT: 2013 Academy Awards. WEAR: On Jennifer Lawerence: Dior Haute Couture gown; On Anne Hathaway: Prada gown. If you were to take a time machine back to the 2013 Oscars, youâd know that the buzz was all about Jennifer Lawerence and Anne Hathaway. Lawrenceâs fall up the stairs to her acceptance speech and Hathawayâs âcontroversialâ dress were the talk of the town. But the attention should have been focused on how they both handled the night with such grace (which is easy to do when youâre wearing Dior or Prada) and took away Oscars, too.
WHO: Lupita Nyong’o . WHAT: 2014 Academy Awards. WEAR: Prada gown; Fred Leighton jewels and headband. Genuinely speaking, there is not a more iconic Oscars red carpet moment in recent history than Lupita Nyongâoâs 2014 ensemble. What made this look historic (other than her win of Best Supporting Actress that year) was this crystal-pleated, powder-blue, deep V-neck Prada gown. We could stare at this look forever.
WHO: Jennifer Lopez . WHAT: 2015 Vanity Fair Oscar Party. WEAR: Zuhair Murad Couture dress; white fur. Itâs no secret that Jennifer Lopez has her fair share of iconic looks; however, none quite hold the same place in my heart as her 2015 Oscars After-Party outfit. Yes, her Ellie Saab gown for the ceremony was stunning, but nothing quite distills the âJ.Lo aestheticâ like this full-length sequin Zuhair Murad Couture dress and white fur stole. My only question is, does love not cost a thing? Because this gown sure looks like a million bucks.
WHO: Emma Stone. WHAT: 2015 Academy Awards. WEAR: Elie Saab gown. Let it be stated for the internet records that Emma Stone is secretly that girl who always brings her A game to the red carpet. Case in point: the green floor-length, high-slit, and sequinned Elie Saab gown she wore to the 2015 Academy Awards. This isnât a bad look; itâs a super-bad look if you catch my drift.
WHO: Jane Fonda. WHAT: 2015 Vanity Fair Oscars Party. WEAR: Zuhair Murad Haute Couture jumpsuit . Whenever I see another red carpet look from the one-and-only Jane Fonda, I always pray that I can look as fabulous as her when I grow up. Of course, it doesnât hurt to be able to wear a full-sequin Zuhair Murad Haute Couture jumpsuit, but then again, itâs Jane Fonda, and no one else can serve a red carpet look like her.
WHO: Kerry Washington. WHAT: 2016 Academy Awards. WEAR: Atelier Versace gown; Schutz shoes. Whether youâre a Scandal fan or just a Kerry Washington stan, the power of the ensemble she wore to the 2016 Oscars can not be understated. She slayed that carpet like a gladiator in head-to-toe (the ponytail, the Atelier Versace gown with a leather bodice and a high-slit, and the see-through Schutz heels) perfection.
WHO: Zendaya . WHAT: 2018 Academy Awards. WEAR: Giambattista Valli Couture dress; Brian Atwood shoes; Bvlgari jewelry. Thereâs not a day that goes by that I donât think about the incredible celebrity and stylist pairing that is Zendaya and Law Roach. The style companions have served us some of the most iconic red carpet looks to date, including this stunning floor-length, off-the-shoulder, chocolate-brown Giambattista Valli number. Zendaya, why do you do this to me?
WHO: Saoirse Ronan. WHAT: 2018 Academy Awards . WEAR: Calvin Klein dress; Christian Louboutin shoes; Cartier jewelry. Compared to the over-the-top numbers the Oscars red carpet has seen in the past, Saoirse Ronanâs strapless pink Calvin Klein dress isnât overly exuberant. But the oversize bow in the back makes this a lesson in understated elegance. This look could have been worn to the Oscars in the â50s or could easily make a statement well into the future. Thatâs what makes it iconic.
WHO:  SZA . WHAT: 2019 Academy Awards. WEAR: custom Vivienne Westwood dress; Jennifer Behr hairpins; Bvlgari jewelry; Stuart Weitzman Nudist Disco shoes . The great thing about the Oscars is that sometimes our favourite musicians will be nominated for film scores and show up wearing some of the best looks of the nightâthat was the case with SZAâs 2019 Oscars look. The stunning custom Vivienne Westwood dress with a corset bodice and a frayed hem had her looking like a supermodel.
WHO: Billy Porter. WHAT: 2019 Vanity Fair Oscars Party. WEAR: Christian Siriano tuxedo dress . The Oscars red carpet hasnât always been known to host the most stand-out looks from nominated actors and attendees, but every once in a while, weâre blessed with a few men who arenât afraid to go bold. It doesnât get bolder than actor and style icon Billy Porterâwho else could pull off a Christian Siriano tuxedo dress? This is an Oscars red carpet look weâll be talking about for years to come.
WHO: Gemma Chan. WHAT: 2019 Academy Awards. WEAR: Valentino Haute Couture dress; Bvlgari jewellery; Jimmy Choo shoes . No one has ever entirely made a case for hot pink on the Oscars red carpet like Gemma Chan. Her voluminous Valentino Haute Couture gown is something I stare at when I feel I need a reminder that there are, indeed, beautiful things in the world.
WHO: Regina King . WHAT: 2019 Academy Awards. WEAR: Oscar de la Renta dress; Chopard jewellery; Christian Louboutin shoes . The 2019 Academy Awards was a huge night for Regina King, as she not only won Best Supporting Actress for the film If Beale Street Could Talk, but she also donned one of her best red carpet looks to date. Of course, King fans are well aware that sheâs often one of the most stylish characters on-screen, but the stunning white Oscar de la Renta gown paired with matching Christian Louboutin shoes proved sheâs a style icon IRL, too.
WHO: Lady Gaga. WHAT: 2019 Academy Awards. WEAR: Alexander McQueen dress; Tiffany & Co. jewellery. If you werenât already a self-proclaimed Little Monster (like myself), the 2019 Oscars could have felt as if a star was born that evening. Of course, real Lady Gaga fans know sheâs served iconic looks for years; her Oscar win (for best original song), the Alexander McQueen dress, and the yellow Tiffany & Co. necklace had her shininâ like never before.
WHO: Sandra Oh. WHAT: 2020 Vanity Fair Oscars Party. WEAR: Cong Tri dress; Messika jewellery; Stuart Weitzman shoes. One person can bring life or death by serving a look, and thatâs no other than Greyâs Anatomy and Killing Eve star Sandra Oh. Her 2020 Vanity Fair Oscars Party look (a grey, floor-length, sequinned, feather-embellished, deep V-neck Cong Tri dress) had me in shambles.
WHO: Janet Mock. WHAT: 2020 Vanity Fair Oscars Party. WEAR: Oscar de la Renta dress. By now, you know that a list of the best Oscars looks of all time is subjective and ever-changing in the face of trends. Occasionally, there are hidden gemsâlike this Oscar de la Renta look Janet Mock wore to the Vanity Fair Oscars Partyâthat go unnoticed. But with time, reflection, and a whole lot of sequins, weâre able to see that the best Oscars looks of all time strike the perfect balance between being timeless and being of that time period. How to know if something can be considered stylish is in the eye of the beholder, I guess, but for now, Iâll keep staring at these looks.
