Oscars Fashion: The 50 Best Dresses of All Time

Charlize Theron

Charlize Theron snagged Oscar gold in 2004 for her uncanny portrayal of serial killer Aileen Wuornos in Monster. But on Oscar night, the South African bombshell showed nary a trace of her character's extra poundage, greasy hair or gnarly yellow teeth, instead using a perfectly toned form and sun-kissed glow as canvas for a gorgeous slinky, beaded backless number by Gucci. 

Charlize Theron

With the perfect amount of old-school screen siren and a fresh rusty tangerine hue to modern things up, Charlize Theron again wowed at the Oscars in 2000, this time in Vera Wang. 

Courtney Love

You never quite know what you're going to get with Courtney Love, and the 1997 Oscars were no exception. Only instead of the itchy hangover grunge motif that still comprises the Hole frontwoman's usual look, Love shocked and awed — in a good way! — by sporting a classically polished, white satin Versace gown to that year's Academy Awards. Perhaps someone should make a sequel to The People vs. Larry Flynt, if only to give Love a reason to look like a functioning member of society once again. 

Farrah Fawcett

Farrah Fawcett (then going by Farrah Fawcett-Majors) took her role of effortless California girl quite seriously at the 1978 Oscars, preferring to accessorize her liquidy gold Stephen Burrows dress with only a clutch and a smile. The juxtaposition between the downplayed styling and high-wattage frock worked wonders and proved why Fawcett still deserves to be remembered for her breezy, confident fashion sense today. 

Gwyneth Paltrow

Long before she was teaching chic mommies how to brown their Passover-friendly schnitzel just so, Gwyneth Paltrow was a 23-year-old star in the making, with some pretty heavy arm candy in the form of Brad Pitt. And in 1996, she hit up the Oscars in a stunningly simple Calvin Klein sheath that began her trajectory of the classic yet head-turning Oscar outfits to come. 

Gwyneth Paltrow

Case in point: The otherworldly column gown (also by Calvin Klein) she sported at the 2011 awards, where she accessorized with colorful pieces of Louis Vuitton jewels and performed a country song. The screen siren-esque look was so good, we won't even hold the aforementioned croonage against her. 

Hilary Swank

In 2005, Hilary Swank accepted her best actress statue for Million Dollar Baby wearing a dramatic midnight blue Guy Laroche gown, which, with long sleeves, a high neck and sweeping open back, managed to be refreshingly sophisticated in the sexiest of ways. 

Jennifer Lopez

In 2003, when Bennifer was in full swing, Jennifer Lopez turned a corner from her usual breed of jaw-dropping, sex-oozing garment and opted for a uniquely classic, mint green Valentino number on the Oscars carpet. The asymetrically draped gown was exotic and grown-up and didn't appear to require the use of double-sided tape. Score. 

Julia Roberts

The vintage velvet-and-satin Valentino stunner Julia Roberts wore to win her best actress award for Erin Brockovich might have originated in 1982, but it looked perfectly in place and modern at the 2001 ceremony, too. 

Julianne Moore

It's a fact: Redheads in green are good. And as Julianne Moore proved at the 2003 ceremony, specific redheads in green Tom Ford for Yves Saint Lauren Rive Gauche gowns are as good as they come. 

Julianne Moore

In 2010, Moore did it again in an opalescent Calvin Klein column gown that oozed frost and glamour. 

Lauren Hutton

Like Farrah Fawcett after her, model Lauren Hutton had the naturally gorgeous look down at the 1975 Oscars, opting to pair her pastel-flecked chiffon Grecian gown with a simple metallic belt, clutch and goddess-like glow in lieu of jewelry. 

Madonna

Michael Jackson on her arm, $20 million in Harry Winston diamonds and a blinding Bob Mackie sequined gown — no, Madonna didn't opt for low-key at the 1991 Academy Awards. But she looked like an old-school movie star anyway and still retained her signature pluck. And in the end, that's the true mark of successful style. 

Marion Cotillard

Marion Cotillard channeled a modern mermaid in the elaborately beaded Jean Paul Gaultier fishtail gown she wore while accepting best actress honors at the 2008 ceremony for La Vie en Rose. Both Edith Piaf and Princess Ariel would be proud.

Michelle Williams

Michelle Williams was a burst of chic, sophisticated sunshine in the pleated, mustard-hued Vera Wang number she wore to the 2006 awards. Her loose, romantic bun and bold red lips only added to the simply powerful look. 

Nicole Kidman

Say what you will about John Galliano and his missteps, but there's no disputing that the embroidered chartreuse Dior creation he designed for Nicole Kidman in 1997 ushered in a new era of daring, fantasy-filled red carpet dressing that remains to this day. 

Sandra Bullock

The red strapless Marchesa ball gown that Sandra Bullock wore to the 2011 Oscars is as elegant and movie star-ready as Oscar dresses come. 

Sharon Stone

Sharon Stone made sartorial history in 1998, when she snagged a crisp white button-down from then-husband Phil Bronstein's closet, paired it with a satin Vera Wang full-length skirt and headed out to the most important fashion show in the world. Today, it's cool-girl de riguer to steal from the boys and sport looks that have an edge of androgyny, and we have Stone to thank. 

Sofia Coppola

Sofia Coppola and Marc Jacobs have long had a love affair, starting in 2002 when the designer chose the filmmaker to be the face of his fragrance. So it was only natural that Coppola chose his graceful, black satin V-neck gown for the 2004 Oscars, where she won the best original screenplay award for Lost in Translation. 

Amy Adams

Judging by the sequined L'Wren Scott stunner Amy Adams wore to the 2011 Oscars, redheads look good in deep blue, too. 

Anjelica Huston

It's easy to forget that Smash star Anjelica Huston was once a model and It Girl who long held Jack Nicholson's heart. Seeing her in the long-sleeve, sequined scoop-neck dress she wore to the 1976 Oscars, however, offers a fantastic memory jog.  

Anne Hathaway

Anne Hathaway looked like beacon of light in Armani Prive at the 2009 Oscars. Which is great, considering a mere two years later she, uh, bombed as the show's host. At least her dresses were good then, too. 

Beyonce

Beyonce's enviable, strong style has been creating girl crushes since long before her recent Super Bowl performance. And this glamour-filled Atelier Versace look, which she sported to the Oscars in 2005, is sophisticated while keeping the performer's signature edginess intact. We dig. 

Cate Blanchett

If fairy dust and a moon beam had a baby, we're convinced it would look like the magical graphite-hued Armani Prive gown that Cate Blanchett wore to the 2007 Oscars. 

Catherine Zeta-Jones

The scarlet red Versace gown worn by Catherine Zeta-Jones in 1999 perfectly played up the Welsh beauty's dark raven-hued hair and fair skin, creating an almost modern Snow White situation that worked very well. 

Cindy Crawford

At the height of the '90s supermodel era in 1991, Cindy Crawford wore a red plunging Versace to the Oscars and solidified her role as leader of the supermodels, even more. 

Diane Kruger

Diane Kruger always pushes a boundary or two when getting dressed, and her choice of this black and white Chanel gown to the 2010 Oscars is no exception. Grown-up yet frilly at the same time, the dress further established Kruger's rep as a bold style risk taker, albeit one with usually successful results.

Elizabeth Taylor

The violet, plunging Edith Head gown that Elizabeth Taylor donned at the 1970 Academy Awards brought out the legend's violet eyes and, uh, showed off her assets. She looked fantastic, as usual. 

Freida Pinto

John Galliano strikes again with this stunning electric blue, Indian-inspired number worn by Freida Pinto in 2009. 

Grace Kelly

At the 1955 ceremony, Grace Kelly looked every bit a would-be princess in a frothy green satin gown by legendary costumer Edith Head. As the cover of Time magazine said about the iconic actress in January of that year, "Gentlemen prefer ladies." And this dress proves why.  

Gwyneth Paltrow

GOOP did it again last year in a chic, simple, asymmetrical Tom Ford dress and matching cape. 

Halle Berry

in 2002, Halle Berry became the first black woman to take home a best actress statue, which she did for her work in Monster's Ball. And the scarlet-tinged, strategically embroidered Elie Saab gown she sported while doing so was the cherry on top of the historic evening's sundae. 

Jada Pinkett Smith

Usually clad in body-hugging styles, the interesting, circa-1950s Antonio Canovas del Castillo for Lanvin gown looked lovely on Jada Pinkett-Smith at the 2002 Oscars. 

Kate Winslet

Back in the early aughts, some of Kate Winslet's red-carpet looks definitely were better than others. But the red Ben de Lisi column gown she wore to the 2002 ceremony melded the simplicity she's now known for with a visually interesting floral neckline that made the dress worthy of such an important event. 

Katherine Heigl

Clad in a dramatic red Escada gown at the 2008 Oscars, Katherine Heigl looked like a bona fide movie star. End of story. 

Helen Mirren

In 2007, Helen Mirren won best actress for her work in The Queen, wearing a bodice-skimming Christian Lacroix gown that many half her age would have trouble pulling off with anything close to the same amount of sexiness and grace. 

Milla Jovovich

At last year's Oscars, Milla Jovovich busted out the classic glitz in a vibrant white, sequined Elie Saab one-shoulder gown. Paired with her frosty nails, modern chopped haircut and Edie Parker clutch, the results were stellar. 

Natalie Portman

Both strong and soft at the same time, Natalie Portman looked every bit the modern Audrey Hepburn in her Grecian Lanvin gown at the 2005 Academy Awards. 

Nicole Kidman

The red backless Balenciaga halter gown worn by Nicole Kidman in 2007 would have been beautiful without the dramatic back bow, mini train and hint of metallic piping at the bodice. But with those touches, it was nothing short of spectacular. 

Nicole Richie

In 2010, Nicole Richie's beaded Reem Acra set the bar for all fellow free spirits who wish to go glam. 

Penelope Cruz

The epic, sculptural Atelier Versace gown chosen by Penelope Cruz in 2007 truly erases any blurred lines between fashion and art. 

Reese Witherspoon

The metallic-tinged circa 1955 Dior gown that Reese Witherspoon wore to the 2006 Oscars was a prim and pretty nod to June Carter Cash, the portrayal of whom scored Witherspoon a best actress prize that year for Walk the Line. 

Renee Zellweger

The simple silhouette and canary coloring of Renee Zellweger's strapless, vintage Jean Desses gown gave a proper lesson in how to dress like a movie star at the 2001 Oscars. 

Sienna Miller

Sienna Miller makes no apologies for her boho, free-spirited ways. And the tribal-tinged, turquoise and gold Matthew Williamson frock she wore while accompanying Jude Law to the 2004 Academy Awards perfectly captured that essence in a chic, worldly way. 

Tilda Swinton

Tilda Swinton's decidedly unique style may not appease every fashion fan. But the beautifully draped nude-and-black Lanvin number she wore to the 2009 Oscars deserves to be celebrated for its interesting blend of avant-garde allure.

Uma Thurman

Prada was merely a purveyor of nylon knapsacks when Uma Thurman wore Miuccia Prada's lovely layered lavender gown to the Oscars in 1995 -- the year she was nominated for best supporting actress for Pulp Fiction. The rest, as they say, is history. And as we all now know, Prada does a lot more than backpacks. 

Vanessa Paradis

Johnny Depp's onetime better half has a free-spirited, gothic style that makes her a cult figure in cool-girl circles. And the shimmery, black V-neck gown she sported at the 2005 Oscars lived up to her signature aesthetic by being sexy in an unsaccharine way. 

Vivien Leigh

At the 12th Annual Academy Awards in 1939, Vivien Leigh won best actress for playing Scarlett O'Hara in Gone With the Wind. And the dress she wore while doing it earned a spot on our list for having an abstract floral print and geometric side cutouts that make it way ahead of its time. 

Zoe Saldana

Zoe Saldana has compared the trippy Givenchy Couture gown she wore to the 2010 Oscars to an "Avatar dream." We'll just call it wildly creative and contemporarily elegant and leave it at that.

Audrey Hepburn

No Oscar dress list is complete without Audrey Hepburn. The iconic actress looked every bit the modern movie star in a sweet, ivory lace gown designed for her by longtime sartorial collaborator Hubert de Givenchy in 1953, the year she won best actress for her work in Roman Holiday.