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HC’s Picks for The Top 10 Oscar Looks Of All Time

Ahh, the Oscars.

It’s the most-coveted award in Hollywood, representing that crowning moment of glory for actors and actresses when the endless audition gigs, filming days and scathing reviews seem worthwhile. Winning an Oscar solidifies an up-and-coming star’s place in Hollywood history and with this year’s Oscar nominations including top contenders like The Artist, Girl with the Dragon Tattoo, The Iron Lady and The Descendants, we’ll be seeing a number of famous A-listers like George Clooney, Brad Pitt, Angelina Jolie, and Steven Spielberg take home the gold. It’s a night of Oscar statuettes, red carpet glam, and Hollywood magic (not to mention glasses of bubbly). And every year, celebrities step out in stunning red carpet ensembles, hoping to make the best dressed list on Oscar night.
 
 “If you want a custom gown sketched by a designer with beading and embroidery, that can take many weeks to prepare,” Marilyn Heston, head of MHA, an LA-based international company that pairs celebrities with designers and luxury brands, tells The Hollywood Reporter.“It’s not an overnight deal to get a spectacular Oscar dress. Generally, these tailor-made dresses are only offered to nominees and presenters for the Globes and the Oscars. If a designer spends all that time and money on a gown, they want to make sure that it will end up in Vogue or Women’s Wear Daily. This is not an artistic endeavor. The only reason a global designer is dressing an actress is to gain exposure that will raise awareness and increase sales.”
 
From ‘50’s style icon Grace Kelly to modern day red carpet trend-setter Angelina Jolie, we put together a list of the 10 all-time greatest gowns to grace the Academy Awards red carpet, worn by some of the big screen’s most memorable ladies. Click through to see if your favorite nominee made the cut.

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Marilyn Monroe, 1951

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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Although blonde bombshell Marilyn Monroe never won an Oscar herself, that didn’t stop her from getting a spot on our best dressed list. The usually vivacious and voluptuous vixen showed a more demure side at the 1951 Oscars. As a presenter that year, she opted for a chiffon off-the-shoulder gown with a white fur shrug and ruby red lipstick. Her style has been (not so easily) mimicked by other celebrities to grace the Oscars red carpet over the years.
 
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Audrey Hepburn, 1954

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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Audrey Hepburn is known for popularizing “the little black dress,” but she’s often forgotten for her other memorable fashion moment: the little white dress. She was garbed in one of her favorite designers, Givenchy, on the red carpet for the Oscars in 1954. She accepted the award for Best Actress for her role in Roman Holiday that evening, wearing a white Givenchy gown with floral embroidery.The dress, which showed off Hepburn’s delicate shoulders and petite figure, best captured the starlet’s essence at the time: innocent, yet strikingly sophisticated.
 
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Grace Kelly, 1955

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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America’s Hollywood sweetheart turned Princess of Monaco, Grace Kelly donned this gorgeous silk gown by Edith Head on the night she won the Best Actress Oscar for The Country Girl. At the time the dress was the most expensive in Oscar history (the blue champagne material alone cost $4,000) and this dress (profiled on the cover of Life) helped to solidify the Academy Awards as a fashion event.
 
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Elizabeth Taylor, 1961

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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The raven-haired Hollywood legend wore a stunning princess-cut gown with a yellow top, a white floral-patterned skirt, and a black belt adorned with a red rose. She topped off her look with white gloves and a touch of her signature bling: sparkling diamond drop earrings. She won the Best Actress award for her performance in Butterfield 8 that year, but she still makes fashion lists today with that look. 

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Halle Berry, 2002

 

 

 

 

 

 

 

 

 

 

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Halle Berry took home the Oscar gold in 2002 for her performance in Monster’s Ball, but she also stole the show on the red carpet in this memorable Elie Saab gown. With its sheer, embroidered top and burgundy skirt, it’s undoubtedly one of the most talked-about dresses to hit the Oscars red carpet ever.
 
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Hilary Swank, 2005

 

 

 

 

 

 

 

 

 

 

 

 

 

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If you got it – flaunt it! That’s what Hilary Swank did, showing off her toned back in this navy blue backless gown by Guy Laroche.

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Heidi Klum, 2008

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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It’s no easy feat to upscale the red carpet itself. But that’s exactly what supermodel Heidi Klum managed to do at the 2008 Academy Awards with this incredible dramatic Gallino gown. She flaunted her assets in this voluminous scarlet Gallino gown (which would have put the Queen of Hearts herself to shame) and was without a doubt one of the most eye-catching stars of the night.

 
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Angelina Jolie, 2009

 

 

 

 

 

 

 

 

 

 

 

 

 

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This international do-gooder actress always sets the red carpet abuzz and 2009 was no different. She was back in black with her draped, strapless Elie Saab couture gown. She added just a touch of glitzy color with a 65-carat Colombian emerald ring and emerald earrings from Lorraine Schwartz.
 
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Zoe Saldana, 2010

 

 

 

 

 

 

 

 

 

 

 

 

 

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Zoe Saldana’s lovely look from the 82nd annual Academy Awards is one of the most fun and flirty Oscar dresses to date. On her Givenchy couture gown, the purple ombre coloring gives it a playful side but the dramatic hem and shimmery bodice adds definite sexiness.

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Natalie Portman, 2011

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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A very pregnant Natalie Portman made maternity look positively chic in this plum silk chiffon draped Rodarte gown at the Academy Awards last year. The actress, who was a Best Actress nominee for her lead role in Black Swan, already had a close relationship with Rodarte designers Kate and Laura Mulleavy, who helped design the costumes for the dramatic thriller. While I love the dramatically beautiful gown, that new-mommy glow doesn’t hurt either!

Did your red carpet favorite make the cut, collegiettes? Name your most memorable Oscar dresses in the comments box below!

Alexandra is a graduate from the University of New Hampshire and the current Assistant Digital Editor at Martha Stewart Living. As a journalism student, she worked as the Director of UNH’s Student Press Organization (SPO) and on staff for four student publications on her campus. In the summer of 2010, she studied abroad at Gonville and Caius College, Cambridge University, in England, where she drank afternoon tea and rode the Tube (but sadly no, she did not meet Prince Harry). Since beginning her career, her written work has appeared in USA Today College, Huffington Post, Northshore, and MarthaStewart.com, among others. When not in the office, she can be found perusing travel magazines to plan her next trip, walking her two dogs (both named Rocky), or practicing ballet. Chat with her on Twitter @allie_churchill.