Grace Kelly epitomized elegance in this mint green Edith Head gown. White opera-length gloves added a classic touch.
Barbra Streisand donned this sparkling Arnold Scaasi pantsuit when she won her first Oscar in 1969 — a look considered quite daring at the time.
Cher was ready to hit the stage in this Bob Mackie showstopper, complete with feathered headdress and bare midriff.
The early ’90s was the era of the supermodel, and there was no bigger pairing than Cindy Crawford and Versace.
Elizabeth Hurley’s timeless dress would be appropriate in any era.
Celine Dion literally turned heads in this reverse Christian Dior tuxedo.
Oscar winner Gwyneth Paltrow had a princess moment in this pink Ralph Lauren gown.
Perhaps the most notorious Oscars look of all time, Bjork’s Marjan Pejoski swan dress ruffled a few feathers with the fashion elites.
Jennifer Lopez left quite an impression at the Oscars in this Chanel haute couture gown, which featured a see-thru top.
Julia Roberts proved some looks are timeless in this vintage Valentino from the designer’s 1982 collection.
Kate Hudson found herself on many worst-dressed lists in this overly ornate Stella McCartney dress. Looking back on her disastrous Oscars debut, Hudson says McCartney joked, “‘Look babe, it was the hair wasn’t it?'”
Cameron Diaz paired a 19th-century Indian necklace from Fred Leighton as a belt for her floral Emanuel Ungaro dress. The result was a breezy, bohemian look.
Faith Hill sang “Somewhere Over the Rainbow” in this appropriately multi-hued Versace dress.
Halle Berry won best actress in this elegant Elie Saab gown with delicate floral embroidery. It’s one of the most memorable dresses in Oscars history.
J.Lo toned things way down for her 2003 Oscars appearance, wearing a mint, one-shouldered Valentino sari-style gown inspired by one Jackie Kennedy wore in 1967.
A blonde and bronze Charlize Theron channeled classic Hollywood glamour in this glittery Gucci gown. ’40s-style finger waves completed her look.
Diane Keaton wore this head-to-toe menswear-inspired look in 2004.
Nights in white satin, indeed! Angelina Jolie wore this simple yet stunning Marc Bouwer gown in 2004.
Some thought Uma Thurman’s Christian Lacroix gown resembled the Swiss Miss hot chocolate icon.
This buttercup Valentino couture gown was made specifically for Cate Blanchett by the Italian couturier himself.
Hilary Swank showed off her sculpted body (earned while training for Oscar-winning role in “Million Dollar Baby”) in this navy, back-baring Guy Laroche gown.
Charlize Theron took a color risk in this olive, vintage Dior gown. Big bows would make many appearances on future carpets.
This asymmetrical, burgundy Vera Wang gown gave the slender Keira Knightley a bombshell silhouette.
Reese Witherspoon reportedly found this 1955 Christian Dior gown at a Paris vintage boutique, and had to convince the shop owner to part with it.
Many felt the big black bows on Anne Hathaway’s Valentino dress were unnecessary.
Michelle Williams’ canary yellow Vera Wang gown provided a bold burst of color on the red carpet.
Vogue’s Andre Leon Talley selected this Oscar de la Renta dress and mini-bolero for Jennifer Hudson, a decision the Oscar winner reportedly regretted.
Kate Winslet’s mint green Valentino goddess gown fit like a dream.
High collar and high drama!
Nicole Kidman looked statuesque in this red Balenciaga gown, featuring a giant bow tied at the back of her neck.
A dramatic departure from her 2006 dress, Reese Witherspoon arrived in a purple Nina Ricci dress with an ombre cascading train.
Marion Cotillard looked like a mermaid in this John Paul Gaultier dress with hundreds of shimmery silver scales.
Anne Hathway redeemed herself from 2007 with this flawless, figure-hugging Giorgio Armani Prive dress.
The rosettes on Charlize Theron’s Dior dress got mixed reviews. Regardless, the South African beauty still looked incredible.
This ruffled Versace dress showed off Demi Moore’s incredibly fit physique.
Sandra Bullock wore this silver Marchesa column gown the year she won best actress. No blind side here, all eyes were on her!
“Avatar” and “Star Trek” actress Zoe Saldana looked out of this world in this dramatic number. Her Riccardo Tisci gown had a lot going on: tiers of tulle, ombre, and a sparkly gold top.
Best dressed list regular Cate Blanchett donned this unique lilac Givenchy Haute Couture with intricate pearl beading. Pops of yellow at the collar added even more visual interest.
As a Dior spokesperson, Natalie Portman was expected to wear the brand in 2011. But after head designer John Galliano went on an anti-Semitic rant, the Jewish actress decided to go with this Rodarte instead. This pretty plum dress showed off her pregnancy curves.
Angelina Jolie got a leg up — or a leg out — on the competition for best dressed in this sexy Versace dress. Her bare leg even had its own Twitter account.
Jennifer Lopez brought the va-va-voom in this sexy Zuhair Murad dress, and (nearly) suffered a wardrobe malfunction while presenting on the main stage.
On the opposite end of the spectrum was Gwyneth Paltrow, who looked conservatic chic in this pure white Tom Ford column gown and cape.
Meryl Streep looked like an Oscar statuette in this gold lame Lanvin gown.
Fashionistas would easily recognize Alicia Vikander’s exquisite gown as the work of Lebanese designer Elie Saab.
Amy Adams looked heavenly in this light-as-a-cloud gray Oscar de la Renta gown.
Anne Hathaway’s pink Prada dress with ill-placed darts was actually a last-minute replacement. The actress had planned to wear Valentino, but discovered her dress was similar to costar Amanda Seyfried’s dress and opted to change.
Jennifer Lawrence may have tripped on this voluminous Dior haute couture gown while accepting her best actress award, but she still looked amazing.
Naomi Watt’s custom gunmetal grey Armani dress was a standout in the sea of fluffy dresses.
Cate Blanchett looked ethereal in this nude Armani Prive dress, reportedly worth $100,000. An additional $18 million in jewels added that extra sparkle.
Kate Hudson’s Atelier Versace gown was a sexier version of the caped one Gwyneth Paltrow wore in 2004.
Best supporting actress winner Lupita Nyongo looked regal in her headband and pale blue Prada gown.
Green is always a flattering color for redheads, but this lime beaded Elie Saab gown elevated Emma to a whole new level of elegance.
Jennifer Lopez finally opted for sophisticated over sexy in this Elie Saab creation.
Julianne Moore donned this Karl Lagerfeld-designed custom Chanel on the way to winning the best actress award.
Lupita Nyong’o donned a Calvin Klein creation encrusted with 6,000 pearls worth $150,000. The dress was actually stolen after the ceremony and later return, with the thief claiming the pearls were fake.
The always fashion forward Lady Gaga wore a white jumpsuit by Brandon Maxwell.
Cate Blanchett turned to Armani Prive again in 2016, donning this sea-foam feathered gown with plunging neckline.