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Iconic Dresses That Broke Major Red Carpet Rules

Olivia Di Pede

March 27, 2018

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Over the years we’ve seen almost everything when it comes to red carpet fashion! From feathers to sheer paneling to lace and leather, nothing is off the table. We’ve come to realize that the pieces that push the boundaries while still looking elegant are often the types of dresses that land on the best-dressed list, but there is definitely a fine line between risky and rule-breaking. Follow along for 12 iconic celebrity dresses that broke major red carpet rules:

11. Sarah Jessica Parker — 2017

In 2017, Sarah Jessica Parker stepped out in this crisp white number breaking one of the unspoken rules of the red carpet! Rather than opting for a designer frock, the fashionista rocked a dress straight from a bridal runway collection. It’s not often that we see a celebrity wearing a legitimate bridal dress on the red carpet, so this was definitely a notable red carpet rule-breaking fashion moment.

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10. Sharon Stone — 1998

It typically takes a star months to carefully select what dress she’s going to wear to the Academy Awards. They must decide between designers, specify a color and shape and undergo alterations to ensure a perfect fit on the big day. In 1998, Sharon Stone decided to forgo this entire process and simply opted for her then husband’s simple Gap button-up shirt for her Oscar attire. Of course, she styled it in the most polished way possible with a lavender Vera Wang silk skirt, but the fashion choice still came as quite the shock to red carpet fashion critics.

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9. Celine Dion — 1999

Celine Dion shocked everyone when she appeared on the Oscars’ red carpet in 1999 wearing this white silk tuxedo and top hat combination! At this time tuxedo suits were slowly becoming more prominent on the red carpet after seas of lavish gowns had been the norm for years, but it was more so the way Dion styled her look that left jaws dropped. Dion rocked her suit completely backward and allowed the V-shape of the lapels to act as an open back. The look was seriously cutting edge, but we’re quite certain it broke more than a few fashion rules that evening.

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8. Cher — 1988

Cher is undoubtedly one of the first names that comes to mind when thinking about the biggest red carpet rule breakers. Her looks over the years for the Academy Awards have always been quite bizarre and she’s definitely adopted an “anything goes” approach to her red carpet fashion. This look from the 1988 Oscars was definitely one of her most memorable from the sheer skirt, dramatic ruching and shimmering sparkles throughout.

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7. Elizabeth Hurley — 1994

No one could possibly forget the rule-bending look that Elizabeth Hurley wore to the 1994 Oscar awards. Her scandalous look consisted of a cleavage-baring deep V neckline and revealing cutouts trailing down her torso which were held together by oversized safety pins. Despite breaking quite a few red carpet etiquette rules, the dramatic look changed the way people dressed on the red carpet for years to follow and many designers began to adopt the safety pin trend into many of their runway designs.

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6. Juliette Binoche — 1997

Juliette Binoche broke all the red carpet rules when she attended the Oscars in 1997 wearing this burgundy velvet creation! Surprisingly the look is actually not a dress, it’s a coat buttoned up with a dramatic popped color, which was completely innovative at the time. The look was very vampire-esque and definitely took quite a few people by surprise.

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5. Bjork — 2001

No one could possibly forget Bjork’s 2001 Oscars dress that was shaped like an actual swan. We’re quite certain there was a fashion etiquette rule or two that this look broke and it has been one of the most criticized red carpet fashion decisions in all of history. Allegedly Bjork even pretended to lay an egg on the red carpet on the night of the event, which we’re quite certain must have thrown the Academy into a frenzy.

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4. Halle Berry — 2002

Halle Berry’s 2002 Oscar dress was definitely iconic, but did it break a few red carpet fashion rules? We definitely think so! Ths sultry look featured a burgundy silk skirt which was paired with a sheer bodice that was covered with floral applique and strategically covered all the right places. The look was scandalous, to say the least, and definitely caught the attention of a few fashion critics for bending all the rules.

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3. Diane Keaton — 2004

For years women always opted for extravagant gowns for red carpet events, but recently things have shifted and now pantsuits and tuxes are totally acceptable for women to rock as well. Diane Keaton, however, definitely broke boundaries when she stepped out wearing this full-blown tuxedo back in 2004. The look definitely caught the eye of a few critics, but mostly because it was overall quite unflattering, especially with the top hat. We love a statement power suit, but this look drowned her and came across more bizarre than respectably unique.

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2. Selena Gomez — 2013

Selena Gomez may be one of the most well-dressed women in Hollywood now, but that’s not to say she didn’t break a few red carpet fashion rules back in the day. When Selena first broke into the scene she didn’t seem to care for designers and instead opted for dresses from affordable brands, such as this one-shouldered number from Forever 21! Although she’s part of huge luxury fashion campaigns now, there was certainly a time when she broke red carpet rules and opted for budget-friendly fashion instead.

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1. Gwyneth Paltrow — 2002

Gwyneth Paltrow’s Oscar look from 2002 was definitely a risk that was not well rewarded! The goth-inspired look featured a full satin skirt and a sheer bodice that definitely broke rules and turned a few heads. Paltrow, however, recognized the fashion blunder and admitted later in life that she wished she had chosen something different for the event. “There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to – a little bit of punk at the Oscars,” she said.

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Olivia Di Pede

Olivia loves all things fashion, beauty, and entertainment. In her free time, she can be found taking yoga classes, reading thriller novels, and styling outfits on Instagram.