This article was last updated on April 16, 2022
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Getting one woman into one outfit for one evening can be a multi-million dollar affair… so why is it that as more money, resources, and star-power is being pumped into the system, red-carpet looks feel like they’re becoming more and more blah?When the economy of “playing it safe” feels pervasive at every star-studded event, we’re particularly thankful for the few iconoclasts who make fancy-pants dressing a daring, whimsical, and mega-fashionable event. Just because the invite says black tie, that doesn’t mean you can’t wear a see-through pajama set (We love you, Babs!) or lay an egg before the wall of paparazzi (We love you too, Bjork!). Here’s to the 15 trailblazers who do the red carpet the way it should be done.
Nominated for her role in Funny Girl, a movie that celebrated personality over a pretty face, Barbra Streisand wore a see-through sailor suit designed by Arnold Scaasi and what might have been the world’s first fancy hot pant. We expected nothing less from this envelope-pushing lady.
Cher has never been one for subtlety, and this one-of-a-kind Bob Mackie “dress” definitely put her on a whole other level, fashion-wise. Cher reportedly donned this creation as a proverbial “eff you” to the Academy who snubbed her 1985 filmMask, because they didn’t think she was a serious enough actress. Beautiful andprovocative — that’s a combo we can get behind!
Elizabeth Hurley took the fairly tame dressing culture of the mid-’90s and shook it by its pleated-front foundations. The safety-pinned Versace number she wore to the Four Weddings and a Funeral premiere was appropriate for neither a wedding nor a funeral, but so sexy and in-your-face, we’re sure nobody minded.
Sharon Stone famously wore a gray Gap turtleneck to the 1996 Oscars, when she couldn’t find anything to go under her Valentino dress. The next year, she pulled the ol’ high-low card once again by wearing her husband Phil Bronstein’s white Gap button-up with a stunning Vera Wang skirt.
With fresh daisies tucked into her platinum-dyed hair, coupled with enviable wine-colored lips, Drew Barrymore was the picture of the ’90s when she presented at the 1998 Oscars.
With a neckline down to there, J.Lo pulled a Barbra Streisand at the 42nd Grammy Awards in a tropical-print Versace dress that launched a thousand…ab routines. To see a grown-up, sophisticated, talented woman to wear something so daring wasso refreshing… plus, she did the palm print nearly a decade before it started trending!
Created by Macedonian designer Marjan Pejoski, the swan dress is proably one of the most unforgettable gowns ever worn on the red carpet. Ever inimitable, Bjork didn’t let “black-tie attire” come between her and her style. Plus, can we all talk about that genius egg clutch? We can always appreciate a lady who pays attention to the small things.
Nominated for Best Actress at the 77th Academy Awards, Hilary Swank knew she had to make an impact. Opting for a Guy de Laroche dress, Hilary’s high-necked, long-sleeved dress seemed to be more appropriate for an aging star than a buzzing talent on the verge of superstardom. But as she turned around, the plunging back shouted a statement: Just try and ignore this woman as she leaves you in the dust!
In a mustard-yellow Vera Wang gown,Michelle Williams showed off a high-wattage look that had none of the gimmicky trappings of previous red carpet “best-dressed” moments. In a vintage cut, an unusual color, simple accessories, and a casual updo, Michelle was the picture of a modern-day fairy-tale princess.
On the cusp of her rise to becoming Fashion’s #1 Darling, Diane Krugerbrought simplicity, posh polish, and veryshort skirts back to the red carpet. Every single one of her outfits since this Jason Wu cocktail dress has been a winner.
In a jaw-dropping Christopher Kane galaxy-print dress, Carey Mulligan became one of the first young actresses to prove that baring it all or dressing like a child was not the only way to be noticed. Sophisticated and smart dressing is something that’s achievable at any age. So…Elizabeth Olsen, Elle Fanning, Jennifer Lawrence? You can thank Carey for paving the way.
Wearing a Givenchy couture beaded gown that looked like something an Alien High Priestess might wear to her wedding (that’s a good thing), Cate Blanchett proved that weird and glamorous can seamlessly go hand-in-hand.
No matter what Tilda Swinton wears, her six-foot frame, procelain complexion, and arresting profile guarantee she’ll be the most stand-out person in any room. But never one to minimize anything, Tilda embraces her unconventionality with equally off-the-wall ensembles that always plays to her androgynous looks and avant-garde sensibilities. Weird women everywhere salute you, Tilda!
Octavia Spencer won an Oscar at the 84th Academy Awards, and did it in a supremely beautiful, effortlessly glamorous Tadashi Shoji stunner. Cinched at the waist and splashed with silver sparkles, the gown was understated and impactful at the same time — much like the kind of acting Octavia is known for.
How could we leave out the leg? We’re not sure if anyone paid attention to Angelina Jolie‘s Versace dress at this year’s Oscars, but they sure fixated on her peek-a-boo leg. Though the mother of six has mostly stayed out of the public eye of late, here, she proved that she’s still got the world hanging on her every action… even if it’s only a outwardly turned leg.
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