Pushing boundaries comes with the territory in the world of fashion. However, not many people have been able to successfully execute a fashion risk in the way the following ten style pioneers have. From personally designing edgy fashions to showcasing the work of innovative designers, no one does it quite like this group of notorious names in fashion and pop culture.

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1. KARL LAGERFELD

Karl Lagerfeld first started fronting collections for the now defunct Jean Patou fashion house. He made headlines even in the 60’s for breaking fashion rules by designing skirts for the brand that were considered too short during that time period. Now having established enough clout in the industry to pretty much do whatever he wants, Lagerfeld is still pushing boundaries by using porn stars as runway models when he’s not mixing running shoes with couture dresses.

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2.CHER

Cher has always been a style icon and pioneer of the less is more way of dressing. Consistently wearing sequins, flashy colors and flesh exposing outfits (even to this day) has cemented her as one of the first female musicians to make it socially acceptable. The infamous outfit from her “Turn Back Time” music video is no exception. That song debuted in 1989 but the picture above is from the 70’s. She’s been pushing the boundaries of fashion for well over 40 years.

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3. GRACE JONES

Before Gaga, there was Grace. In fact, I’m going to go on a limb and say that Grace Jones pretty much pioneered the living art form of dressing. From colorful couture to hair dyes, body paints, head pieces and out of this world accessories, no one broke the rules quite like Grace until recently.

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4. MADONNA

Pairing wedding dresses with waist belts emblazoned with the words “boy toy” while singing a song about a sexual experience that rivals losing your virginity? Breaking the rules is kind of what made Madonna famous. From the infamous breast cones pictured above to baring it all for an art book entitled “Sex,” Madonna has always been at the forefront of limit crossing media.

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5. MICHAEL JACKSON

Michael Jackson is not only the king of pop, but the king of flashy fashion. No strangers to sequins, clasps, brooches, a solo sparkling glove, gold accents or soldier style shoulder padding, Michael was always breaking style rules by wearing something that only he could make look appealing and popular.

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6. PHARRELL WILLIAMS

Pharrell Williams has always been at the forefront of edgy fashion. Making it okay for men to sport handbags, mashing street wear with a formal men’s suits and wearing oversized Vivienne Westwood hats is not an attempt for attention but simply another typical clothing option for this rule-bending trendsetter.

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7. JEREMY SCOTT

Jeremy Scott is one of my favorite couture designers because he simply does what he wants. Transforming Moschino into a fashion house of higher regard, his style of making remarks about pop culture using brand play mixed with fashion has made him one of the critically acclaimed rule breaking designers of the new millennium.

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8. LADY GAGA

Lady Gaga used to seem like a copycat. Wearing variations of styles that had been previously seen on the likes of Cher, Grace Jones and Madonna kept her standing out in appearance but constantly under the microscope of comparison. She chalked it up to homage. That is, until she wore the infamous meat dress. Instantly affirming her personal uniqueness, Lady Gaga cemented herself as one of the top fashion rule breakers of all time. Dressing in shocking outfits to this day, I don’t know if anything she does from now on will ever top the meat dress.

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9. RIHANNA

Rihanna may have started out as a singer but has transformed herself into a style icon. Seemingly wearing clothing that becomes trendy before garnering mainstream status, she officially became a boundary pusher of fashion when she wore that infamous sheer crystal dress, braless, to the 2014 CFDA Awards.

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10. MILEY CYRUS

There’s something about Miley Cyrus‘s current style that made me feel like she belonged on this list. I don’t know if it’s the pixie cut, body revealing outfits or her dramatic metamorphosis from Disney star to debauchery spokesperson. Either way, Miley’s breaking some major fashion rules with her edgy style choices and newfound desire for exposure.