Celebrities Who Defy Beauty Convention

With the ever-present pressure of today’s fashion and beauty trends, it can be difficult and intimidating to carve your own style identity. Here, celebrities who have dared to forge their own path, and who have done so with the kind of success and savvy that can silence even the loudest critic.

Michelle Obama
The Chicago native broke the buttoned-up and play-it-safe mold of previous first ladies by brazenly baring her now-trademark toned arms everywhere from formal state dinners to date night with the president. “Style icons have learned to show off and always highlight parts of their bodies that they love,” says style and beauty expert Mary Alice Stephenson. Indeed, studies have shown that the mere act of working out boosts confidence and positive body image—we’re sure the “Let's Move!” campaigner would agree.

QUIZ: How Much Do You Move? 

Madonna
When the Material Girl burst onto the music scene in the ‘80s, no one would’ve guessed her success in the spotlight would go on to span 30+ years. “Madonna doesn’t let age hold her back,” says Stephenson of the now 53 year-old star. “She takes fashion chances, and has always been a rule-breaker. She shows women who are over 50 that you don’t need to tone it down.” Unwilling to retire her fishnets, stilettos and penchant for black liquid liner, we’ll venture to guess we haven’t seen the last of the Queen of Pop’s career.

QUIZ: Find Your Best Eye Makeup

Cher
Often imitated by drag queens and idolized by the LGBT community on whose behalf she passionately advocates, Cher’s explosive sense of style transcended designer labels and social mores—and often landed her on “Worst Dressed” lists. The legendary designs Bob Mackie created for the star (like this peacock headdress for the 1986 Oscars) were often panned by critics as “garish,” yet redefined boundaries and ignited the free-spirited imagination of girls—and boys—for generations to come.

Tilda Swinton
Hailing from royal lineage that can trace its descendants back to the Middle Ages, Brit actress Tilda Swinton’s fashion identity borrows from the same sense of refined avant-garde. The 51 year-old throws social mores aside with the embrace of androgynous dress and bare-faced beauty on the red carpet, which is further emphasized with a dyed platinum white crop cut. Studies show that color contrast is what allows us to distinguish between genders in milliseconds; but for one who lives to define and not be defined, it’s all about blurring those lines.

MORE: The Science of Why Makeup Works 

Dolly Parton
Perhaps no other entertainer is as well-known for the size of her bosom as she is for her small-town Southern girl humor (“I’m not offended by dumb blonde jokes because I know I’m not dumb—and I know I’m not blonde,” the star has famously said). Yet Dolly Parton is also known for working some of the biggest hair in the business. Thick, voluminous locks are a sign your body is healthy, fertile and nourished with a nutrient-rich diet—a classic evolutionary psych clue that we’re sure isn’t lost on Dolly. (And how long does it take to do that ‘do? “How do I know? I’m never there!”—another classic line from the star.)

MORE: How to Get Voluminous Locks

Björk
Icelandic singer Björk’s unique range of sound has crossed such differing genres as rock, folk, jazz and electronica—and the 46 year-old’s sense of style has proven equally eclectic. It was a swan dress by Macedonian designer Marjan Pejoski that Björk wore to the 2001 Oscars (and in which she ‘laid’ six eggs on the red carpet) that launched the artist’s career in the spotlight. “Before, it was younger girls who were allowed to have more fun with fashion, take risks, show skin,” says Stephenson. “But now, a woman of any age can dare to go there.”

Sofia Coppola
Sofia Coppola is Hollywood royalty; father Francis Ford Coppola is a directorial genius, while cousins Nicolas Cage and Jason Schwartzman regularly light up the silver screen. Yet casual simplicity—which is seemingly at odds with tinsel town’s love of luxury and excess—is the hallmark of the 40 year-old, who favors ballet flats and shifts over cleavage-baring gowns and stilettos. “As women age, they tend to pile on the makeup, jewelry and accessories,” says Stephenson. “But lightening things up and going more understated ends up making you look more youthful.”

Helena Bonham Carter
The glossy flawlessness of the typical leading lady’s red carpet turn stands in stark contrast to what has become the slightly disheveled, off-kilter and ironic style of Helena Bonham Carter. With fascinator hats, petticoats, layers of tulle and satin that harken another era, it’s no surprise the Brit-born actress cites Marie Antoinette as a source of inspiration. With opulence and excess an indicator of upper class distinction that dominates human history from the Egyptian pharaohs to the beheaded French Queen of excess, might the sardonic star be communicating that she’s she’s a level above mere copycat trends?

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Cyndi Lauper
Girls just wanna have fun—and Cyndi Lauper has shown her idea of a good time is playing hair color chameleon. From cartoon yellow to carrot orange, hot pink, blue and beyond, the now 58 year-old Queens, New York native has truly experienced the full spectrum of the rainbow. Hair color and offbeat fashion were playgrounds for the teenage singer decades before she hit it big, though Lauper’s peacock-like use of color to both lure the eye of the public and express herself as an artist grew brighter and more outlandish the more success and fame came her way.

Dita Von Teese
Going against the grain of what is considered de rigueur in the showgirl industry—bronzed skin, blonde hair and impossibly thin perfection—Dita Von Teese brought the retro vision of the curvaceous 1930s pin-up back, “putting the tease back in ‘striptease,’” as the burlesque star is known to say. With pale white skin that sharply juxtaposes jet black hair, red lips and nails, Von Teese’s style is all about contrast, which evolutionary experts say is the most potent yet subconscious signal of feminine health and fertility. Is that really any surprise, coming from a woman whose business is the art of seduction?

QUIZ: What's Your Body Shape?