17 Most Iconic Red Carpet Dresses

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As we bid adieu to yet another manic red carpet season, we look back upon the most famed dresses to ever hit Hollywood. Sparkles, safety pins and plunging necklines galore, here are our picks for the 17 Most Iconic Red Carpet Gowns and the mean, lean, styling machines behind these oh-so memorable looks.

Jennifer Lopez in Versace

1Jennifer Lopez

In what will forever be one of the sexiest looks to ever grace the stage, the Versace gown Jennifer Lopez wore to the 42nd Grammy Awards is just as fresh today as it was on that fateful day in 2000. With the assistance of stylist to the stars Andre Lieberman, this stunner drove Jennifer straight toward the fashion Hall of Fame, with a navel-grazing neckline and vibrant tropical print forever equaling fierce.

Halle Berry in Elie Saab

2Halle Berry

A sheer bodice, floral embroidery and a fabulous fall color palette are all it took to skyrocket Halle Barry toward style icon status. The Elie Saab number she sported at the 2002 Academy Awards showcased her killer bod to perfection, plunging her to the furthest depths of Dream Girl status.  Celeb stylist Phillip Bloch referred to the dress as their “magic moment”.

Jennifer Lawrence in Dior Haute Couture 

3Jennifer Lawrence

Oscar nominee Jennifer Lawrence played the princess role to perfection as she walked the red carpet of the 2013 Academy Awards. Cementing her spot as a premier style starlet, Jennifer Lawrence rocked this Dior Haute Couture number with confidence, tumble down the stairs and all. As the fresh face at the forefront of the high-fashion brand, she’s certainly got her pick of the litter and with the help of supreme fashion stylist Rachel Zoe, the memory of this pale pink gown is sure to stick for years to come.

Gwyneth Paltrow in Ralph Lauren

4 Gwenyth Paltrow

Channeling the eternally chic Grace Kelly, Gwyneth Paltrow rocked the red carpet of the 71st Academy Awards in this too-pretty-for-words Ralph Lauren frock. In a look reminiscent of a red carpet Barbie, Gwyneth in this sexy-meets-sweet ball gown of taffeta is equal parts prom queen and Old Hollywood, a stunning combination forever embedded in the minds of style lovers throughout the world.

Angelina Jolie in Atelier Versace

5 Angelina Jolie

Bringing a whole new meaning to the term “Peek-a-Boo”, Angelina Jolie’s 2012 Oscars’ Atelier Versace gown will ever remain one of the most spoofed red carpet gowns of all time. While velvet and red carpet events don’t usually go hand-in-hand, the rich texture of this Jen Rade-styled look is sure live on as one of the most glamorous uses of a thigh-high slit.

Elizabeth Hurley in Versace

6Elizabeth Hurley

In one of the fiercest red carpet looks ever, Elizabeth Hurley commanded attention as she flaunted her enviable figure in cleverly placed cut-outs at the Four Weddings and a Funeral premiere along side Hugh Grant in 1994. As one of the House of Versace’s most recognizable works of art, the safety pin dress will live on in fashion history as one of the edgiest — ergo most scandalous — dresses to ever grace the red carpet.

Hilary Swank in Guy Laroche

7Hillary Swank

Much like the mullet haircuts of yore, it’s business in the front and party in the back when it comes to Hilary Swank’s 2005 Academy Awards dress. Today’s breed of sexy backless dresses pale in comparison to Hilary Swank’s Guy Laroche frock, styled by celeb stylist Kate Young. Showcasing an enviable bod and an impeccable fashion sense, this timeless navy frock endures as one of the most clever uses of a cut-out the red carpet has ever seen.

Bjӧrk in Marjan Pejoski

8Bjork

Arguably the most controversial dress in the history of the red carpet, the Marjan Pejoski swan dress Bjork wore to the 2001 Academy Awards was anything but conventional. A sheer bodysuit, crystal embellishments and tons of tulle make for some truly fascinating fashion, though no stylist these days would dare dream dressing their client in such a risk.

Cher in Bob Mackie

9Cher

In a stylish act of rebellion, Cher’s choice to rock this Bob Mackie showgirl get-up had tongues wagging well past the show’s end. As a long-time friend of the designer, Cher and her custom two-piece complete with gigantic feather headdress will forever serve as a reminder that in fashion, there’s always room for a little fantasy.

Sharon Stone in Vera Wang 

10Sharon Stone

Yes, the white button-down and long skirt combo has been done to death, but no one’s pulled it off quite like the effortlessly glamorous Sharon Stone at the 1998 Academy Awards. Creating one of the most impactful high/low mixture to grace the red carpet, this Gap shirt and Vera Wang skirt pairing will go down in history as one of the most timelessly chic ensembles ever.

Lady Gaga in Armani Prive

11Gaga

Delightfully outlandish in all its high-fashion glory, the Armani Prive dress Lady Gaga rocked at the 52nd Grammy Awards is among the most unusual to hit the red carpet.  With the brilliant mind of Former Haus of Gaga Fashion Director Nicola Formichetti responsible for this fierce sartorial statement, gaga was no doubt at home in the out-of-this-world frock.

Penelope Cruz in Atelier Versace

12Penelope Cruz

Stylist Estee Stanley recalls Penelope Cruz’s 2007 Oscars gown as one of the proudest moments in her career. With a little help from a tiny little fashion house called Versace, Stanley’s choice to dress Penelope in this intricate blush gown is not lost upon the minds of fashion admirers.

 Rihanna in Giorgio Armani

13Rhiannha

Never did basic black look so chic. Highly glamorous and with an unmistakable air of sex appeal, the tastefully revealing Armani dress Rihanna rocked to the Grammy Awards in 2012 further demonstrated the songbird’s edgy persona. The result of a collaboration with the designer himself, this 1970’s, Scarface inspired look remains one of the hottest to grace the Grammys.

Sandra Bullock in Marchesa

14Sandra Bullock

Rumor has it that Hollywood’s top stylists duked it in order to secure this stunning Marchesa number for the 2010 Academy Awards. Clearly, Sandra Bullock’s stylist Deborah Waknin dominated. Shimmery, semi-sheer and with gorgeous embroidery of epic proportions, this dress must have been made with Hollywood royalty in mind.

Angelina Jolie in Marc Bouwer

15Angelina Jolie 2

Style so nice, she’s on our list twice. With the help of longtime stylist Jen Rade, Angelina’s Marc Bouwer dress skimmed her curves in the most effortless of ways, solidifying her place as one of Hollywood’s hottest. It’s no surprise that stylish stars love a “white moment” on the red carpet, but no one’s done it quite like Angelina since then.

Madonna in Bob Mackie

16Madonna

Portraying the epitome of Old Hollywood glamour, the Bob Mackie creation Madonna rocked alongside Michael Jackson at the 1991 Academy Awards is one of the most luxe looks we’ve ever seen. Longtime stylist Arianne Phillips credits Madonna for changing the face of fashion forever.  Looking every bit the mega star she was, this look remains one of our favorite Madonna looks ever, which is saying a lot.

Nicole Kidman in Balenciaga

17Nicole Kidman

Red dresses on the red carpet are far from ground-breaking, but the Balenciaga Nicole Kidman sported to the Academy Awards proved the power of the shade nonetheless. Created just for her, the form-fitting style (complete with bow!) fit Kidman like a glove, showcasing her statuesque shape and supreme sense of style. Bravo!

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