25 Most Controversial Trendsetters

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25 Most Controversial Trendsetters
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If there's one thing everyone loves about fashion, it's a style scandal. No, we're not talking anything dirty -- we're talking debates in apparel (Is it a do or a don't?), questionable red carpet looks (Oh, no she didn't!) and of course, the shocking looks that make these trendsetters famous (Hello, Gaga.). Many style innovators made our jaws drop across the decades, but who's the most controversial trendsetter? Madonna? Prince? Katy Perry? Explore our countdown to find out who nabbed our number-one spot. Don't forget to share your opinion on who made (or didn't make) our list!

25. Katy Perry
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25 Katy Perry

California-born singer-songwriter Katy Perry boldly expresses her candy-coated aesthetic. With record-climbing hits and sold-out tour dates across the globe, this pop sensation's outfits are as outrageous as her success. Despite her bright, themed costumes, colorful wigs and flair for the absurd (we're lookin' at you, giant yellow block hat), Perry has unconventional appeal that goes beyond the shock factor. With a line of OPI nail polish and her passion for retro fashion, Perry embraces her wacky wardrobe with a sense of humor. And, people love her for it -- just ask her millions of fans.

24. Jennifer Lopez
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24 Jennifer Lopez

J.Lo is known for many talents, including her fashion sense. From when she was just Jenny from the block to her head-turning red carpet moments, J.Lo has balanced her chic style with controversial red carpet looks, like the famous green Versace dress (pictured here). As an actress, producer, singer designer and host of "American Idol," Lopez has become a household name and fashion icon who pays tribute to her heritage and inner diva, one extraordinary look at a time.

23. Venus Williams
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23 Venus Williams

Being one of the greatest tennis players of all time has perks. For Venus Williams, the freedom to express her fashion sensibility on the court is one of them. Yet Williams' unconventional tennis outfits have stirred much debate. She and her sister Serena were first known for wearing brightly colored gear and beaded hair. They defied convention, trading in traditional white tennis skirts for brighter colors and modern silhouettes -- not without criticism. Venus even had to forfeit a match due to a runaway hair bead. Venus' flamboyant designs continue to evolve, especially in designs from her collection, "Eleven."

22. Aaliyah
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22 Aaliyah

R&B singer Aaliyah serenaded us with her phenomenal voice and chart-topping hits in the '90s, and she rocked the boat with her unique sense of style as well. Aaliyah often wore tube tops with baggy pants and boxers or a thong that showed at the top of her waistline -- two trends that women across the country embraced to show off their sexy tomboy style and fit physiques. Her signature look earned her model status for Tommy Hilfiger, who featured her "classy but sexy" appearance in his ads.

21. Diane Keaton
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21 Diane Keaton

Her breakout role in "Annie Hall" made actress Diane Keaton's unique fashion sense famous. She was able to combine her passion for menswear and hats -- two wardrobe essentials she has since popularized. Though she's associated with these items, Keaton's unique sense of style is about more than menswear and millinery. "I feel about shopping the way I feel about imagery," she told the "New York Times Magazine." "There’s not a designer I don’t look at. I’m always interested in the material and cut."

20. Courtney Love
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20 Courtney Love

Dubbed the "Most Controversial Woman in the History of Rock" by "Rolling Stone," singer Courtney Love could also be called the "Queen of Grunge." As the frontwoman for all-female alternative rock band Hole, and wife of the late Kurt Cobain, Love held the title with tousled blonde bedhead, smeared red lipstick and an endless supply of off-shoulder tees and school-girl skirts. Love combined her eccentric outfits with outrageous behavior, leading a generation of rocker chicks who defied the typical "girl next door" aesthetic with a skull-ringed flip of the bird.

19. Tupac Shakur
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19 Tupac Shakur

Tupac Shakur, aka 2Pac, was widely known for his controversial rap music about ghetto life, gang violence and sex. He sold millions of albums filled with songs about racism and prison life. He was also known for his signature bandanna and chain, as shown on the T-shirt worn by rapper Nas, who paid tribute to the deceased rapper at the 2004 VH1 Hip Hop Awards. While he was both admired and feared, due to his influence among young gang members, he is a respected rap icon. His song "Dear Mama" was added to the National Recording Registry in 2010.

18. Betsey Johnson
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18 Betsey Johnson

Who else would cartwheel on the runway at Fashion Week? Whimsical designer Betsey Johnson's signature style manages to hit sweet, sexy and edgy notes all at once, as she flirts with the boundaries between costume and couture in apparel and accessories. Her collections are both beautiful and brash, with layers of loud animal prints, lace and hot pink. "New York Magazine" called her aesthetic "punk-cum-Warholian," the ideal combination for teens when they search for the perfect prom dress.

17. David Bowie
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17 David Bowie

Today's gurus of guyliner (calling Adam Lambert) owe their gender-bending fashion sensibility to the original pioneer of glam rock, singer and actor David Bowie. From his wild hair, makeup and costumes to his sense of showmanship, Bowie has a flair for out-of-this-world performances, epitomized by his characters Ziggy Stardust and Thin White Duke, which propelled him to super stardom. And we've yet to see a male star to date who can work a dress like Bowie on the cover of his third studio album, "The Man Who Sold the World."

16. Dolly Parton
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16 Dolly Parton

A big voice, big hair and big... country style (what?) have made Dolly Parton one of country's most recognizable singers. From her larger-than-life blonde hairdo, to her sparkly pantsuits with a touch of Southern belle, Parton's fashion influence is as large as her success. Wigs, bold makeup and intricate beaded gowns are favorites, but she has also garnered attention for her unapologetic affinity for cosmetic surgery. "If I see something sagging, bagging, and dragging, I'm going to nip it, suck it and tuck it," she famously told Oprah Winfrey.

15. Cher
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15 Cher

Many trends go back to Cher's status as a recording powerhouse and actress in the '60s and '70s -- some that may surprise you. Her jet black long hair, bell bottoms and bare midriff earned her sex symbol cred as she donned inventive outfits (often designed by Bob Mackie) on stage and television. Cher was the first person to show her bellybutton on TV. Today, after decades of statement-making clothing and hairstyles, this comeback queen has become a fashion icon in the gay community, continues to create music and is proving she isn't about to go away any time soon.

14. Grace Jones
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14 Grace Jones

Mixing feminine and masculine styles was de rigueur for Grace Jones from the '70s to today. As a direct contrast to the hyper-feminine "Charlie's Angels" look that dominated the late '70s, Jones embraced androgyny, becoming a muse to artist Andy Warhol. He photographed her extensively, making her image as noteworthy as her music. Jones had several pop dance hits and was a regular nightclub Studio 54 with her wild, square-cut hair and angular padded jackets. During the '80s, she inspired the cross-dressing movement and wore memorable body murals on her 5'10'' frame. Jones continues to act, produce and record music.

13. Elton John
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13 Elton John

Everybody's favorite pop music composer and recording genius, Sir Elton John, is not only a singer-songwriter and acclaimed pianist -- he's a history-making trendsetter and champion of LGBT rights. Wearing outlandish glasses, decorative costumes and stunning platform shoes are just a few of the controversial elements of Elton John's career -- he also came out as a gay man in a 1976 "Rolling Stone" interview, at a time when openly gay performers were few and far between. John also has a foundation dedicated to funding AIDS research and was inducted into the Rock and Roll Hall of Fame in 1994.

12. RuPaul
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12 RuPaul

RuPaul, America's most famous drag queen and creator of the reality series "RuPaul's Drag Race," took glamour to a new level in the '80s when he dressed in gorgeous gowns and performed in clubs across New York City and at gay rights rallies. RuPaul promoted cosmetics as the "First Face of M.A.C." "I get these young kids who are into drag, and really getting their take about what drag means to them, especially since they’ve never been through the gay rights movement or the things that I’ve seen," he told the "New York Times." "I'm getting this fresh perspective about drag."

11. Marilyn Manson
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11 Marilyn Manson

Rocker and iconoclast Marilyn Manson pushes pop culture buttons with his dramatic, twisted fashion sensibility. Pale white foundation, colored contacts, black lipstick and bondage costumes reigned supreme in performances with his eponymous band. Often criticized as a negative influence on youth culture because of his satanic lyrics and attire, Manson maintains a cult following, even within the fashion community. Japanese fashion designer Yoshiki featured Manson in a 2011 runway show, “Asia Girls Explosion." Manson "is the fashion icon in rock’n'roll," said the designer.

10. Prince
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10 Prince

Gorgeous lamé dresses, brocade prints, jumpsuits, galactic booties and the color purple are just a few of the reasons Prince's design aesthetic inspires us (and who can forget diamonds and pearls?). This Grammy Award-winning musician has a wide vocal range, countless flamboyant outfits in his closet and 10 platinum albums. Known for his dynamic performances and stunning costumes, Prince created the "Minneapolis sound," which mixes funk, rock, pop, R&B and New Wave; the guy can also accessorize like nobody's business.

9. Britney Spears
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9 Britney Spears

If the rise and fall of a teen pop icon is measured in costumes, Britney Spears' wardrobe speaks volumes. Her 1999 debut album "...Baby One More Time" featured the belly-baring, naughty schoolgirl of every boy's fantasy, while her later music videos showcased red-latex space suits and barely-there glitter hot pants. Her sex symbol status and chart-toppers led her to break album sales records and become a pop culture phenomenon until her personal breakdown and the Great Buzz Cut of 2007. She's currently working on her comeback. What will she do next? Probably something that'll get us talking.

8. Twiggy
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8 Twiggy

Lesley "Twiggy" Lawson is the famous, saucer-eyed model of the '60s who was the first to make thin in. (No, it wasn't Ms. Moss!) Today, the model, actress and "America's Next Top Model" guest judge has garnered one more feather for her cap: inspiring a generation of women, now in their 60s and 70s, to stay stylish as they age -- aka, the "Twiggy Effect."

7. Patricia Field
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7 Patricia Field

Stylist and designer Patricia Field made "Sex and the City" a live-action magazine spread within a TV show. As the costume designer for the iconic HBO series that brought haute couture into the homes of women across the globe, Field fueled fashion trends (and continues to do so) for women of all ages, shapes and sizes. With four character wardrobes as diverse as their personalities, Field found ways to challenge the style aesthetic of women through Carrie, Samantha, Charlotte and Miranda -- with one of the world's most fashionable cities as her backdrop, New York City.

6. Alexander McQueen
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6 Alexander McQueen

Was Alexander McQueen an artist or a designer? Many have debated the fashion designer's dark world of women's apparel and accessories. McQueen evolved the notion of what is beautiful, through disturbing and breath-taking imagery in his collections that all began with one simple concept and then moved into a storyboard of designs that turned into his garments. The Met's 2011 exhibition "Savage Beauty" illuminated his creative process, explaining his cultural references and showcasing the couture he displayed in dramatically artistic runway shows that were more performance art than catwalk. McQueen designed clothing until his death in 2010.

5. Michael Jackson
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5 Michael Jackson

The King of Pop led fashion trends since the '60s when he was a child star sporting an afro as part of the Jackson 5. In the '70s when he started his solo career, his success skyrocketed with hits like "Thriller," "Beat It" and "Billie Jean." Each had their own iconic looks that have been endlessly imitated since their debut. MJ was an undeniable trendsetter: the red leather jackets, sparkling glove, and even the bright socks with loafers are timeless favorites. Despite his personal struggles and sometimes bizarre behavior, he was beloved by fans until his death in 2009.

4. Madonna
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4 Madonna

If the '80s belonged to anyone, it was Madonna. Upon the release of her first album in 1983, Madonna continually reinvented her look for each new album release. Her fans followed suit. Madonna's music, passion for pushing the envelope and outgoing personality made her one of the most influential musicians in pop music, but she wasn't just a trendsetter when it came to music, clothes, hair and makeup. "Time" magazine named her one of the "25 Most Powerful Women of the Past Century" due to her bold makeover of feminism and passion for sexual liberation among women.

3. Anna Wintour
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3 Anna Wintour

The reigning editor-in-chief of American "Vogue" is not only the tastemaker for one of the most prestigious fashion magazines, she makes or breaks designers, trends and even colors with a simple nod. Known as an intimidating and demanding boss (famously depicted in "The Devil Wears Prada"), Anna Wintour lords over the $300 billion fashion industry. Also a trendsetter in publishing, she was the first to feature a celebrity on a fashion cover, too. It's a testament to her impeccable taste and personal magnetism that we're all taking style advice from someone who hasn't changed her hairstyle since she was 14.

2. Lady Gaga
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2 Lady Gaga

In 2008, Lady Gaga released her debut album, "The Fame," and the fashion world has never been the same. Are they costumes? Is it fashion? From outlandish wigs, glasses, jumpsuits, bodysuits and gowns to her bizarre personas, Lady Gaga has mixed her role as entertainer, LGBT advocate and self-esteem booster in a host of elaborate and instantly iconic outfits. With chart-topping hits and sold-out tours, the songstress has used her fame to support charities and social issues. And, if there's one constant in her wardrobe... it's that it's always changing.

1. Barbie
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1 Barbie

Barbra Millicent Roberts -- aka Barbie -- looks darn good despite her 52 years. Whether she's taking on a new career, dumping her boyfriend Ken again, or donning couture, this doll is a lightning rod for critics of society's double standards for women. At 5'9'' and 110 pounds, she may be better suited for an eating disorder clinic than a Doctor Barbie role, and she's been criticized for those unrealistic measurements and unattainable looks. Yet she represents possibility and power like no other figure. Barbie, welcome to the top of the list.

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