The Academy Awards are one of the most-watched red carpet events in the world (along with the Met Gala, of course). The 94th Academy Awards, no doubt full of memorable and Best Oscar Red Carpet Outfits moments,
This definitive list of our favorite Oscar fashion moments features many iconic looks. Lupita Nyong’o’s sky-blue Prada gown from 2014, when she was nominated for 12 Years a Slave, was a crowd favorite. Nicole Kidman’s unexpected Balenciaga halter dress with a dramatic bow detail, which she wore in 2007, was another standout. And who can forget Charlize Theron’s gilded Gucci gown from 2004, when she accepted Best Actress for Monster looking every inch the Hollywood star?
#1 Lupita Nyong’o in Prada (2014)
Lupita Nyong’o’s iconic Prada gown from 2014 was responsible for elevating the Grecian goddess trope. Just when we thought teal was done for, this gown appeared on the red carpet. This look is still a winner when accessorized with a pearl headband and a shining golden man.
#2 Grace Kelly in Edith Head (1955)
With thin straps and white gloves, this 1950s look is remarkably on-trend for 2022. Grace Kelly wore a matching duster in the same perfect aqua color. A simple updo finished the look, evoking timeless glamour.
#3 Nicole Kidman in Dior (1997)
More is sometimes more is more. This is most emphatically true of Nicole Kidman’s Christian Dior look for the 69th Academy Awards. Tom Cruise pales in comparison to the glory of this impossible-to-name lime and glorious jumble of textures.
#4 Gwyneth Paltrow in Ralph Lauren (1999)
The legend surrounding this gown is deserving of its own Oscar. The dress has an innocent and delightful quality to it, even if the fit is a little off. GP appears ecstatic to be there, and no best dressed list would be complete without this ensemble.
#5 Faye Dunaway in Theadora Van Runkle (1968)
The whole look predates stylists, which adds to its attraction. A black feather-lined duster with tights and black shoes feels impossible to pin down. It’s unexpected and cool, which is a rare combination at the Academy Awards.
#6 Lauren Hutton in Halston (1975)
Hutton’s rainbow-colored Halston creation has appeared on the mood boards of numerous designers. Why shouldn’t it? When paired with the neutral fur jacket, it’s the best of ’70s glamour encapsulated in a single look, made even better by Lauren Hutton’s undeniable charm.
#7 Winona Rider in Armani (2000)
This Armani gown has been a long-time favorite of the actress and is frequently re-worn. With her exacting sense of nonchalance, it’s textbook LBD. The headband and sash dress up the look without taking away from the striking silhouette.
#8 Whitney Houston (1994)
Allow Whitney Houston, an artist at the 66th Academy Awards, to teach the entire red carpet about the power of a suit. The choker necklace and bra explaining in detail peeking out from wide lapels cemented the look as one of the greatest of all time.
#9 Sharon Stone in Vera Wang and Gap (1998)
Another masterpiece, this time in the art of dressing high and low. Sharon Stone pairs a plain white button-up from Gap with a lilac floor-length Vera Wang skirt. Her short hair and bold lips show that this outfit is the key to casual cool for a formal event.
#10 Halle Berry in Elie Saab (2002)
Halle Berry at the 2002 Academy Awards was the precursor to the naked gown. This Elie Saab look is sexy and ethereal thanks to colorful details that give the dress its own personality. Her Oscar win, like this unforgettable work of art, was a watershed moment.
#11 Hilary Swank in Guy Laroche (2005)
Hilary Swank wore a backless outfit in a sophisticated navy blue before it was a trend in 2005. The dress is understated, especially in the front, and it exemplifies the power of doing less.
#12 Diane Kruger in Elie Saab (2006)
Kruger looks stunning in an Elie Saab structural creation. Her undone hair adds a Californian ease to the look.
#13 Keira Knightley in Valentino (2015)
Keira Knightley ushers in a new era of Valentino fairytale gowns. This dress is a welcome change from the usual tight, jewel-tone gowns. It also looks great with her baby bump.
#14 Margot Robbie in Chanel (2018)
Margot Robbie’s Chanel look from 2018 has an architectural feel to it. Her blunt bob lends a casual air to the entire ensemble. Her crystal handbag evokes Old Hollywood, creating a winning mix of old and new.
#15 Janelle Monáe in Ralph Lauren (2020)
Janelle Monáe is one of the few people who can pull off a silver hood on the red carpet with ease and instinct. This outfit, designed by Ralph Lauren as a tribute to its wearer, is truly the first of its kind.
#16 Cher in Bob Mackie (1973)
There’s so much to love about Cher’s look. The two-piece ensemble is now commonplace, but it wasn’t always the norm on the red carpet. Cher’s stick straight hair gave even her most daring ensembles a sleek, ’70s vibe.
#17 Taraji P. Henson in Reem Acra (2017)
The look is reminiscent of Angelina Jolie, but in a way that only Taraji P. Henson can pull off. Black velvet with a slit may appear to be a safe bet, but with such jewels, Henson demonstrates that she can create a look that is anything but boring.
#18 Gemma Chan in Valentino (2019)
Consider this look to be the most refined version of “This outfit has pockets!” Gemma Chan checks all the boxes for a high-glamour glance while remaining her opulent self.
#19 Zendaya in Giambattista Valli (2018)
Zendaya is pictured here in the perfect look for any Oscar presenter to wear to the ceremony. Take careful notes! She’s stylish and casual, with no sequins in sight.
#20 Tessa Thompson in Chanel (2019)
Tessa Thompson wore this Chanel gown in 2019 as a tribute to Karl Lagerfeld. Her half-back hairstyle and the kitsch of the peplum waist lend a retro glam vibe to the look.
#21 Julia Roberts in Valentino (2001)
Sure, it isn’t the most electrifying choice of all time, however this Julia Roberts ensemble appears in almost every “best dressed” discussion. The dress’s simplicity is truly remarkable. That winning smiling face and those stripes are both unique.
#22 Martha Plimpton in Vintage (1989)
This look is one of the greatest looks of all time. River Phoenix and Martha Plimpton look amazing in their vintage ensembles. Timeless isn’t even close to describing how they could be dropped into any decade with these flawless outfits.
#23 Diahann Carroll (1969)
Diahann Carroll looked angelic in this full-sleeved gown she wore to present at the Oscars in 1969. The tiny floral details elevate the look to the next level. Eyelashes from the 1960s and bright eye shadow round out the look.
#24 Claire Danes in Versace (1997)
Skirt and shirt ensembles are uncommon at the Academy Awards. Claire Danes looks like a cool older cousin in this 1997 teal ensemble. This look, both underdressed and buttoned up, is an example of one that works far better than it appears on paper.
#25 Barbra Streisand in Arnold Scaasi (1969)
This ground-breaking look from Miss Streisand is frequently overlooked when discussing the best Oscar outfits. It’s the epitome of a timeless, era ensemble. The sheer detailing, the oversized collar, and the wide legs. It’s a fantastic look.