The Most Major Beauty Moments Ever

When it comes to elements of style, style icons and fashion rebels are naturally intertwined, a match made in endlessly imitated, audaciously cool, fashionably adventurous heaven. It’s only logical the two would go hand-in-manicured, tattooed hand; it takes a degree of daring to launch a trend or do something different, while the vast majority of women are merely doing their best to look “pretty” and milking their smooth blowouts into day three. In the spirit of appreciating the spear-headers of untraditional beauty, here are the most noteworthy moments:

1. Debbie Harry’s Eternally Bleached-Blonde Mane
Before Madonna, Beyoncé, Rihanna, Nicki, Gaga, and the rest, there was Debbie Harry, the Playboy Bunny-turned-East Village rabble-rouser, and the first white chick to rap in a well-known song. But it’s her eternally bleached-out hair for which she’s possibly best known. No surprise the name of her band was inspired by the catcalls she used to hear walking around New York. There was nothing new about being a bottle blonde when she started dyeing her hair in the seventies (hello, Mae West), but what was different about Debbie is not only the fact that she peroxided it herself, she let her dark roots come in, unapologetically. With the high-cheekbone bone structure of a bombshell and the demeanor of a rough-and-tumble punk kid, she’s known for remarking, “It doesn’t hurt to be hot!”

2. Madonna in Desperately Seeking Susan
Madonna was still a relative unknown when director Susan Seidelman cast her in the 1985 comedy Desperately Seeking Susan (they actually lived down the street from one another in downtown Manhattan). Obviously, that didn’t last for long. Not only was a 27-year-old Madonna catapulted into fame soon after, her personal style, which is arguably a scene-stealing co-star in the film, launched countless copycats. But forget about the stacks of rubber bangles and asymmetrical cross earrings. It was all about Madonna’s wildly wavy locks, unfettered and untweezed eyebrows, heavy eye makeup and lipstick (it was the ‘80s after all, so nothing groundbreaking about that), and proudly unshaven armpits. Thirty years later, it’s still all about her self-styled beautiful mess.

3. Kate Moss by Corinne Day for The Face
You simply can’t talk fashion-world Rebels without talking about Kate Moss. It’s she who said, “I remember my mum telling me that you can’t have fun all the time, and I still hold my answer true today when I told her, ‘But why not?’”

In 1990, she bounded onto the scene a scrappy 18-year-old in front of the lens of photographer Corinne Day, and, though neither likely knew it at the time, history was made. With Moss wearing a feathery headdress, scrunched-nose grin, and notably, no top, the black-and-white beach photos welcomed an era of anti-fashion fashion. Because with Moss wearing minimal makeup, if any at all, her freckles proudly on display, they really weren’t about fashion at all. They were about unconventional, naturalistic beauty, and more importantly, Moss’ candid, unfiltered personality. Later Moss remarked, “It’s kind of rebellious to be yourself.” She, of all people, knows.

4. Demi Moore Shaving Her Head for G.I. Jane
Many actresses have shaved their heads for roles (Charlize Theron, Natalie Portman, Sigourney Weaver, Ellen Page, Anne Hathaway, and Mena Suvari, to name a few)

But it’s Demi Moore who set the tone for perhaps the ultimate showing of self-assured rebellion, and in this case, rebellious beauty, when she buzzed her lustrous brunette mane for Ridley Scott’s 1997 film. It’s not statement-making in itself for an actress to sacrifice conventional vanity for a paid role, but the fact that Moore’s tough-as-nails character was a total badass made her move a game-changer. Moreover, she buzzed her hair in the film itself, announcing a brave in-action transformation.

This past spring, Moore’s daughter Tallulah shaved her own head. "I actually watched G.I. Jane two days before I shaved my head. I don’t think I was 100 percent inspired by it, but I think it may have manifested the idea in my mind,” she told Nylon magazine.

5. Drew Barrymore’s Goes Flower Child at the 1998 Academy Awards
A turn as a dangerous teenage sexpot in the Poison Ivy flicks, a real-life run as a preteen party monster, a bad girl gone grunge who flashed her boobs to David Letterman on a 1995 Late Show appearance: In her youth, Drew Barrymore was about as textbook insurgent as a Rebel can get. And her trend-making personal style had a lot to do with her persona.

But it was in 1998 when still-wild Drew liberated herself – and red carpet style, in the process, by showing up to the Oscars with freshly plucked daisies in her lightly curled blonde bob. The flowers would have read hippie-dippy, but paired with a vampy dark-red lip and what appears to be an entire bottle of glistening body glitter, she resembled a neo-grunge fairy nymph…gone black-tie. Many would say that most starlets would never get away with such a look (and that’s probably true), but that’s mostly because they wouldn’t dare attempt it. Nineties-era Drew goes to show: Attitude is everything.

6. Rihanna, Pretty Much All of the Time
t’s impossible to pick a singular instance when perennial Tastemaker and ultimate Rebel captured what it means to be both with her beauty choices. So consider this an homage to Bad Gal RiRi, who considers to inspire and often shock every time she leaves the house.

For a duet performance with Eminem at the 2014 MTV Video Music Awards, she complemented her naturally curly, flowing hair and a timeless red lip with what could only be described as an ironic statement: the word “Fear” emblazoned across her forehead, in classic horror-movie font. That same year, she appeared on the cover of Lui, a French style-meets-sex men’s magazine, with her nipples in their full, bare glory, offset by an exaggerated French manicure, delicate body chain, and throwback bucket hat. She hit up the iHeartRadio Music Awards channeling a neo-goth queen in emerald-green lipstick and allover-the-scalp topknots. Instead of opting for standard, vegetable-dye henna, her hand tattoo (one of many) is permanent. The list goes on…

7. Rodarte’s Pierced Eyebrows on the Spring ’15 Runway
The talk of New York Fashion Week for the Spring ’15 season, which took place in September ’14, was not driven by just the clothes. What really had everyone buzzing were the eyebrow adornments that Kate and Laura Mulleavy bestowed upon their models for their runway show. Fresh, clean faces – think rosy-nude lips, flushed cheeks, and generally bare eyelids – and simple, seemingly air-dried hair set the foundation for the big scene-stealer: brows fully coated with rows of small silver hoops. Lead makeup artist James Kaliardos refused to give away his technique for affixing the faux piercings. “It’s an industry trade secret,” he said. While most girls aren’t outfitting their eyebrows with hardware for real life, it’s been over a year and a half, and this is for certain: Gratuitous body art is back!

8. Cara Delevingne’s Plethora of Tattoos
A lion’s head on her right forefinger. The word “Bacon” on the sole of her foot. Two interlocked Ds on her hip, which happens to be a friendship tatt with fellow model Jourdan Dunn. An ornate design inspired by yantra, aka sak yant tattooing, practiced in Thailand, Cambodia, and Laos. A tiny diamond inside her right ear. The phrase “Don’t worry, be happy” on her chest. A red heart on her left pinky. The word “silence” on her wrist. Shall I go on? As a model who attributes her massive success to her vibrant personality as much as her picture-perfect looks, Cara has redefined the supposed rules of the modern-day supermodel. Nothing illustrates that truth like her unabashed penchant for body ink.

9. Andreja Pejić’s Natural Transformation
When Andreja Pejić, formerly known as Andrej, was discovered at the age of 16 at a McDonald’s in Melbourne, Australia, she was billed as a male model – and was extremely successful as such, storming runways for big-name designers like Marc Jacobs and Jean-Paul Gaultier. Three years later, in 2014, the once-androgynous model who had identified as “living in between genders,” announced her gender-reassignment surgery. Now at only 24-years-old, the towering blonde, who favors a smoky eye and nude lip, is not only a well-established force in the industry, she’s helping make people shut up about whatever notions of gender “norms” they might have. Most recently, in August, she showed off her versatility for a Make Up For Ever campaign, featured in every Sephora window in North America.

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The Most Major Beauty Moments Ever