The Most Iconic Red-Lip Looks Of All Time

Awards season is a bit like prom for grown-ups. But instead of plastic crowns and awkwardly posed photos, we get to see our favorite actors, musicians, and performers don couture and (occasionally) win some serious recognition. That said, the most exciting part for us will always be found on the red carpet, where the beautiful, the wild, and the glamorous show off the work of some of the most influential hairstylists, makeup artists, and manicurists working today.
While much of what happens on the red carpet can feel intimidating to try at home, one thing anyone can copy is a classic red lip. Luckily, not only is the bold look easy to master and pull off — once you muster the courage and just do it already, that is — it can easily steal the show no matter what you're wearing, even a button-down. To wit: Check out Sharon Stone on slide eight.
To celebrate this universal beauty equalizer, we've rounded up some of the most iconic red lips to ever appear at an awards show. Smoky eyes and HD foundation are mainstays on the red carpet, but it's the red lip that always wins the gold.
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Photo: Ron Galella/Getty Images.
Daryl Hannah At The Academy Awards, 1988
The combination of dark sunglasses and red lips is, in itself, iconic. Now add glitter-frame sunglasses, a silver beaded and embellished gown, and Daryl Hannah, and you get one badass red carpet look that is pure OG glamour. It's like a modern interpretation of "diamonds are a girl's best friend," except with the truer notion that red lipstick is, in fact, a girl's BFF.
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Photo: Ron Galella/Getty Images.
Madonna At The Oscars, 1991
Speaking of diamonds being a girl's best friend, Madonna in her Marilyn Monroe incarnation was definitive of elegance on steroids for the music icon. Her trademark gap-tooth grin decorated with siren-red lipstick was a reminder that not all glitz and glam relies on the conventions of beauty standards. Also, that if you're Madonna you can kind of pull off anything.
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Photo: Vincent Zuffante/Star File/Getty Images.
Selena Quintanilla At The Grammys, 1994
Pop star Selena was known for her brick-red lip — it was her go-to beauty look, so much so that MAC announced a forthcoming limited-edition collection celebrating the late star with her signature red lip color. The great thing about having a red lip as your signature is the ease: A quick swipe, and you're done. Let's call it glam-and-go.
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Photo: Time Life Pictures/Getty Images.
Courtney Love At The Vanity Fair Oscars Party, 1995
The queen of grunge, Courtney Love, knows her way around a red lip, and any event she showed up at in the '90s instantly became that much more rock 'n' roll. Take, for instance, the toy tiara and satin slip that served as her evening wear for the event, which she told Vanity Fair journalist Kevin Sessums was "the cheapest wedding dresses we could find." Throw a deep-crimson lip on that look, and Courtney was the picture of so many little girls' dreams of rock stardom in Hollywood.
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Photo: Kevin Mazur/Getty Images.
Nicole Kidman At The Oscars, 1997
Something about the very Baz Luhrmann-esque color scheme going on with Nicole Kidman on this red carpet made her red lip so right for the occasion. The chartreuse Dior satin embroidered gown she wore, paired with a wine-colored lip, gave her a shimmering jewel-like pop of color amid a sea of black and pastels. The moral of the story: Red works with any color.
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Photo: Kevin Mazur/Getty Images.
Winona Ryder At The Oscars, 1997
Amid that sea of pastels on the red carpet at the '97 Oscars was Winona Ryder, who is quite possibly the only person to effortlessly pull off both goth and glamour at the Academy Awards. How? The beaded black lace dress paired with her red lips gave off a cool neo-flapper vibe. With her dark pixie cut, Winona may have come off a bit precious, were it not for that bright-crimson lip that elevated her whole look with a dash of sex appeal.
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Photo: Steve Granitz/Getty Images.
Drew Barrymore At The Oscars, 1998
Only Drew Barrymore could make daisies red carpet-appropriate with her sweet cropped curls and bangs, but it was the raisin-red lip that took it to the next level. While many stars opt for a classic red on the carpet, Drew's deep and broody hue reads so much cooler and youthful (doesn't hurt to have flowers in one's hair when going for a fresh look) at a formal, buttoned-up event like the Oscars.
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Photo: Kevin Mazur/Getty Images.
Sharon Stone At The Oscars, 1998
If you're going to wear a Gap button-down shirt to the Oscars, you damn well better dress it up. While the talk of the red carpet was Sharon Stone's sartorial mall-chic choice, her styling was on-point — including the simple red lip. Her whole look here proves that nothing elevates simple basics to red carpet status like a solid red lip (and a whole lot of confidence).
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Photo: Kevin Mazur/Getty Images.
Cate Blanchett At The Oscars, 1999
Blanchett's radiantly carefree look on this red carpet is the stuff of Parisian-chic dreams: her floral embroidered gown worn with imperfect straight hair and a bright-red smile. It's the perfect balance of ethereal beauty and down-to-earth attitude. We wouldn't be surprised if she just threw her gown on, brushed her hair, and then slicked on a red lip and said, "Okay, I'm ready, let's go to the Oscars."
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Photo: Scott Gries/Getty Images.
Penelope Cruz At The Grammys, 2000
The year Penelope Cruz had the perfect rock-'n'-roll hair at the Grammys she also made the excellent decision to wear this fiery shade of red lipstick. Translation: She made us all want to ditch our flat irons in favor of carefree locks that only require the punctuation of red lips to complete a look.
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Photo: Kevin Mazur/Getty Images.
Michelle Williams At The Oscars, 2006
We can't applaud Michelle Williams enough for wearing this gorgeous canary-yellow confection on the red carpet — and doubly so, adding a cherry-red lip to the look. It is, after all, one of the most showstopping combinations one can wear. While mixing bold primary colors like red and yellow may sound like a potential traffic disaster, it's pure perfection.
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Photo: Steve Granitz/Getty Images.
Gwen Stefani At The American Music Awards, 2012
Stefani's been wearing a version of a red lip since the '90s, and while each color is as beautiful as the last, it's this persimmon shade that we're calling a favorite. This is the cool Gwen-next-door shade, as opposed to her usual art-pop glam. Proof that red need not be unapproachable, this shade is quite the opposite.
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Photo: Jeffrey Mayer/Getty Images.
Angelina Jolie At The Oscars, 2013
Want proof that any lip shape can wear a red lip and look downright amazing? We imagine a lot of people have told Jolie that a bold lip would be "too much" for her full pout, but we also imagine she doesn't like to play by the rules. Either way, any sighting of her famous lips in red is that much more exciting. Mind you, this is the year she also wore that slit-up-to-there dress, so perhaps the red lips were her icing on that jaw-dropping, I-wear-what-I-want cake. Get it, girl.
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Photo: Dan MacMedan/Getty Images.
Rihanna At The Grammys, 2013
Of the many incarnations of Rihanna, this understated, casual-glamour look proves that RiRi can, and will, slay a red carpet no matter what she's wearing, what color her hair is, or, for that matter, what color her lips are wearing. The sleek red gown (with train, naturally) she wore to the 2013 Grammys and her red lips were a match made in red carpet heaven. And did we mention her nails were also the same shade of scarlet? That's how you wear red like RiRi.
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Photo: Rabbani and Solimene Photography/Getty Images.
Dita Von Teese At The Met Gala, 2014
Okay, fine, we admit we cheated a little by including the Met Gala in this roundup, but to not include a classic Von Teese look would have been criminal. In fact, we don't think she has ever met a red lip she didn't love. Her style is so historically rooted in the pinup look, it's hard to imagine her without the lip look. But consistent as it may be, we never get sick of it. The lesson we can all learn? When you find the shade of red that works for you, work it hard.
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Photo: George Pimentel/Getty Images.
Lupita Nyong'o At The Golden Globes, 2014
Nyong'o can do no wrong on a red carpet. Every ensemble is a home run for the actress, and she's left no makeup rule unbroken along the way. A die-hard color devotee on both her lips and eyes, this beautiful shimmery-red lip color and feline flick is unexpected for the risk-taker — and yet one of our favorites. Why? While it may be sheer, it's the perfect balance to her orange-red gown, proof that sometimes a red lip can be soft and still impactful.
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Photo: Anthony Harvey/Getty Images.
Taylor Swift At The Vanity Fair Oscars Party, 2014
Swift loves a red lip — she has sung this, so it is writ. Worn with a smoky eye and a black sequined getup, she's serving up a serious smolder that's equal parts fancy-ball and rock 'n' roll. Thank you, Swift: A bit of edginess on a red carpet is always appreciated.
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Photo: Photo: George Pimentel/Getty Images.
Beyoncé At The Met Gala, 2015
Bey rarely plays up her lips, so it's a treat to see — and another reason why we're sneaking the Met Gala into this story — especially since her vampy wine-red lip is nothing short of killer. The beaded veil adds a bit of noirish flair for Bey, who's just shown us all here that apparently no style, vibe, or time period is beyond her iconic grasp.
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Photo: Jon Kopaloff/Getty Images.
Diane Kruger At The Oscars, 2015
Another red lip and outfit example of how incredibly successful this combo can be. Kruger's red lip ties this whole minimalist-chic look together — without it, it would otherwise be just another red carpet–jumpsuit situation. With her hair casually tied back featuring romantic waves on the side, Kruger's look is an asymmetrical dream that becomes instantly accessible with her lip color.
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Photo: Steve Granitz/Getty Images.
Emma Stone At The SAG Awards, 2015
Stone may be known for her red hair, but the girl can wear a red lip like no one's business. With her hair slicked back and lids dusted with a shimmery shadow, her bright-poppy red pout makes for a simplistic, elegant look.
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Photo: Jason Merritt/Getty Images
Lady Gaga At The Oscars, 2015
The days of Gaga turning a red carpet affair into an experimental performance are sorely missed, but we really don't hate her glamorous phase that's all platinum-white hair and lush red lips. The look is almost austere on her, with hair pulled back neatly, were it not for the little details that echo the brightness of her red lips — the hair ornaments, the menacing utility gloves. It makes red lips look dangerous in a elegant way you wouldn't expect on a red carpet.
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Photo: Jon Kopaloff/Getty Images.
Zendaya At The Academy Of Motion Picture Arts & Sciences Awards, 2014
Zendaya is a girl of many looks — and able to pull off pretty much anything with her supremely confident attitude and grace. This elegant look could possibly come off a bit stuffy on her, were it not for her bright, true-red lip color. Why? It brings a youthful exuberance to the otherwise demure look. After all, if you're as young and gorgeous as Zendaya, why bother with boring beauty looks?
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