We eat up every bit of celebrity gossip we can get, along with everything we love about their music, films, or whatever it is they’re famous for. But perhaps what sticks in our minds even more than the celebs themselves, are their blazon fashion choices.

Britney Spears and Justin Timberlake - American Music Awards (2001)

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Chances are you knew exactly what fashion we were talking about just by this title. Matching blue jean everything was the name of the game for these favorite lovebirds at the fan-favorite MTV awards as the 2000’s kicked off.

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Cher - Oscars (1998)

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At the height of her career, Cher wore her self-proclaimed favorite outfit of all time. This Mackie dress is so stunning, it’s almost otherworldly.

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Bella Hadid - Harper's Bazaar (2018)

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In a risqué outfit that much resembles Kim Kardashian’s vibe with her Skims line, newly minted supermodel Bella Hadid’s controversial cover fashion was one that was unforgettable.

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Elizabeth Hurley - Movie Premiere (1994)

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The gorgeous Elizabeth Hurley has always been known for setting trends, and in this one-of-a-kind pin dress, she shook up not just the award show, but future fashion as we know it.

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Kim Kardashian - Met Gala (2019)

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Kim K. is always one to watch for fashion, and this particular Met Gala look was a whole process to put together. Kim even went through corset training months before the Gala.

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Celine Dion - Oscars (1999)

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Celine Dion is known for being outspoken and doing things her way, off the cuff. This unforgettable fashion look is a prime example. All she had to do was wear that blazer backwards and voila! Forever trend alert.

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Pink - MTV Video Music Awards (2000)

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Pink has always been known to take fashion trends and turn them into something all her own. Case in point here with what she did with low rise jeans and mixing patterns and loads of hair pomade.

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Charlize Theron - Oscars (2010)

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Looking like a literal human embodiment of a rose, Charlize Theron was actually named worst dressed all around for this number, and she didn’t take home an award this year, either.

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Lady Gaga - MTV Video Music Awards (2010)

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Oh, who could ever forget the infamous “Meat Dress” from the 2010 MTV awards? And yes, the entire thing—even the purse—was made from 100% Argentinian flank steak.

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Demi Moore - Oscars (1989)

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Demi Moore knew decades before any of us did that bicycle shorts would be the ultimate fashion trend. The look didn’t exactly translate back in the 80’s, but we can look at it now and totally appreciate it this ensemble.

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Lenny Kravitz - Running Errands (2012)

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The laughs that ensued from this fuzzy scarf that could’ve fit a literal giant still make meme rounds even today, but in Lenny’s defense, New York can get miserably cold in the winter.

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Sarah Paulson - Ocean's 8 Premiere (2018)

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Chartreuse shades paired with canary-esque textures, this light, vibrant, and ultra-cool fashion choice was a very memorable one for AHS alum Sarah Paulson at her all-female led Oceans 8 premiere.

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Rihanna - CFDA Awards (2014)

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Rihanna slayed in this look that would go on to be one of her most famous and one of her self-proclaimed favorites. With head-to-toe sheer glitter, no one pulls off high end fashion like Rihanna.

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Anne Hathaway - Oscars (2007)

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Classy, if a bit understated and over-“bowed”, Anne Hathway’s 2007 Oscar dress was all dreamy cream lace, bows, and simple yet elegant jewelry, hair, and makeup.

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Madonna - Grammys (2015)

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Madonna isn’t doing her thing unless she is causing a scene, and we are always here for it. This glam matador-inspired outfit at the 2015 Grammys was one-of-a-kind legendary, and no one has ever dared replicate it since.

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Meghan Markle - Trooping The Colour Parade (2018)

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Looking effortlessly like a British royal in no time, Meghan Markle’s outfit was perfectly English, with a touch of class and modern fashion only she could pull off.

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Billy Porter - Oscars (2019)

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When it comes to Billy Porter’s fashion, no one surpasses his looks he serves. Case in point at his debut Oscars ensemble that was beyond gorgeous, artistically structured, and quite frankly one of the most ethereal pieces to ever be seen on the red carpet.

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Angela Sarafyan - Vanity Fair Soiree (2017)

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Keeping in theme with her outstanding performance on HBO’s hit show, Westworld, Angela Sarafyan’s revealing Vanity Fair party dress was a piece of architectural artwork like no other.

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Diane Kruger - Golden Globes (2005)

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People didn’t exactly love this Moroccan-inspired frock from the strikingly beautiful Diane Kruger in 2005. The critics couldn’t seem to understand the architecture of the dress, and quite frankly, though the fabric is beautiful, we’re left a little flummoxed, too.

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Rita Ora - MTV Video Music Awards (2018)

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Rita Ora rarely gets a best dressed for her fashion, but she’s never cared much. She wears what she loves, and this snake patterned, see-through number is no exception.

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Katy Perry and Riff Raff - MTV Video Music Awards (2014)

In an attempt to replicate the iconic Britney and Justin look from a decade earlier, Katy Perry and Riff Raff fell sort of flat. The dire appreciation for the former fashion choice is respectable, but just didn’t work.

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Emily Ratajkowski - Bazaar Icons Party (2016)

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Model Emily Ratajkowski loves to push the limits with hemlines and shapes, and this dress was a unique and sexy take on that in 2016 at the iconic Bazaar party.

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Jennifer Aniston and Brad Pitt - Emmys (1999)

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The hair, the glitz, the sunglasses—all of this screams THAT California sun couple who is just about the most chill on the block. Jennifer Aniston could never go wrong with her hairstyles, and this was one we still crush on.

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Britney Spears - MTV Video Music Awards (2001)

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No one will ever forget Britney, the snake, and the belly dancer style getup she wore while performing at the 2001 VMA’s, arguably at the height of her fame.

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Kristen Wiig - Oscars (2020)

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Kristen Wiig took a fashion risk at the 2020 Oscars, after years of sticking with safe, classic choices. The vibrant look was dubbed “The Lasagna Dress”.

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Veronica Vega - MTV Video Music Awards (2019)

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In an outfit that was actually really impressively put together in its realism of the look of the fake cash, Veronica Vega’s inspiration was simple: “Money Maker”.

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Ariel Winter - Emmys (2017)

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After 2 years of dealing with harassment due to her changing body as she grew up in the spotlight, Ariel Winter finally embraced who she was becoming, and she pulled it off brilliantly in this gorgeous ensemble and hair slick.

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Bjork - Oscars (2001)

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Oh, the swan dress! People still talk about this dress from 20 years ago to this day, and if you hear Bjork mentioned, it seems the swan song of her dress is correlated to her immediately, even before her music career.

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Jennifer Lopez - Grammy Awards (1999)

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People still sport this look for Halloween parties all over the world today. The baring tropical dress on the gorgeous J-Lo as she soared in her career was one that left us in complete awe.

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Rose McGowan - MTV Video Music Awards (1998)

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Rose McGowan really put television editors to work when she donned this hardly there dress in the late 90’s. Chainmail and a glitzy thong were about all this fashion piece consisted of.

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Sarah Jessica Parker - Met Gala (2018)

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2018 was a big year for the Met Gala, especially for theme, and SJP did not disappoint. She and Rihanna both had the same idea with the towering, pope-inspired headpiece and handcrafted gown of opulence.

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Hailey Baldwin - MTV Video Music Awards (2017)

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In a sheer, diamond encrusted pantsuit, Haley Baldwin made her debut as a model to take serious at the MTV awards in 2017. Fast forward to now and her style has only gotten better.

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Christina Aguilera - Blockbuster Awards (2001)

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This dramatic look was not only a drastic change from what Christina Aguilera had been wearing previously, but the sheer complimenting of fabrics, makeup, and hair were goddess worthy.

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Anna Chlumsky - Emmy Awards (2016)

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Designer Christian Siriano went bold and risqué with this post-pregnancy dress he created for VEEP star Anna Chlumsky, and though many critics weren’t quite sure what to make of it, Anna was in love with it.

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Miley Cyrus - MTV Video Music Awards (2015)

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Miley Cyrus loves pushing the envelope in fashion, and she especially loves the less coverage the better. Here, she personifies some kind of Mad Max princess, and she’s gone on to say it’s one of her favorite looks.

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Jared Leto - Met Gala (2019)

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In one of the most talked about Met Gala looks ever, Jared Leto kept his fashion choice pretty tame and in theme—it was his accessory that turned heads…literally.

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David and Victoria Beckham - Versace Party (1999)

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Before either of these 2 Brits were fashion icons and creators, they were constantly matching on red carpets as David rose to fame as a footballer, and Victoria stole our hearts as a Spice Girl.

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Jessica Biel - Oscars (2009)

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Looking like a Greek goddess in this Prada cream silk dress, Jessica Biel’s makeup, hair, and jewelry was fit for the heavens, and this choice landed her on the best dressed list.

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Katy Perry - Met Gala (2010)

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Per usual, Katy Perry can turn any theme or moment into a bubblegum frosting one, and that’s exactly what she does here in this Met Gala look, paired with an impeccable diamond piece around her neck.

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Paris Hilton - MTV Movie Awards (2003)

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Low rise, high hems, and barely there fabrics are the name of the game for Paris Hilton, and she does not disappoint as the luxe tan California heiress at the 2003 MTV Movie Awards.

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Carmen Electra - MTV Movie Awards (1998)

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No one does shock value quite like Carmen Electra, and this dress gave us all hope that there was body tape out there that could hold up to the elements.

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Nicki Minaj - MTV Video Music Awards (2011)

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This was not a look that critics loved, as it was hard to look at and translate. Though the outfit is made up of all the best, kooky things about Nicki, it was overwhelming to say the least.

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Brandi Glanville - Oscars (2013)

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In this timeless look, Brandi Glanville almost took her reality TV reputation and threw it out the door. Critics weren’t a fan of the ill fitting of the gown, though.

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Kim Kardashian - Met Gala (2013)

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In this widely criticized look, Kim Kardashian’s floral number did not impress critics or viewers at home. The dress was many times likened to a grandmother’s couch.

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Reese Witherspoon - Cruel Intentions Premiere (1999)

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Still fresh in Hollywood to fame, Reese Witherspoon didn’t quite hit the mark with whatever this ensemble is, but it didn’t take away from the beauty she was radiating even back then.

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Anja Rubik - Met Gala (2012)

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Anja Rubik showcased a slit like no other with her silk, petal-hued dress for the 2012 Met Gala. The strategy of body tape and undergarment placement is amazing.

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Lara Flynn Boyle - Golden Globes (2018)

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Lara Flynn Boyle was criticized heavily for this ballet number at the 2018 Golden Globes, with most critics confused about the look and also worried by the star’s physical gaunt appearance.

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Lil Kim - MTV Video Music Awards (1999)

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The opinions on this outfit were split across the board at the time, but Lil Kim was over the moon happy with her mermaid, risqué piece made all of glitter and sequins. We still gush over this iconic look today.

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Shania Twain - Billboard Music Awards (1998)

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In one of her first appearances after skyrocketing to fame, the beautiful Shania Twain opted for a fairytale look of periwinkle, sequins, and princess curls right out of an Arthurian legend.

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Beyonce - Super Bowl XXXVIII

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You couldn’t represent the look of the 2000’s better if you tried than this understated ensemble worn by Beyonce. UGG boots, tight blazer, and super short schoolgirl style skirt with a flashy belt was every high school girl back then.

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Rihanna - Met Gala (2017)

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In a look meant to represent Parisian petals and punks, this fashion look stunned critics and won the year’s Gala. While most of us non-fashion experts were left scratching our heads, apparently this dress went down in Gala history.

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Rita Ora - MTV Europe Music Awards (2017)

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Ran out of time to get dressed for a big award show? No problem! Throw on the hotel’s bourgeois robe, the most glamourous, heaviest diamonds you’ve got, and blush that make your cheeks look as sharp as a knife. Voila! You’ve got a new fashion trend.

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Solange - Met Gala (2015)

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In an incredible fashion piece that makes us do a double take, this elemental dress was a stunner in its colors, architecture, and shape at the 2015 Met Gala.

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Miley Cyrus - MTV Video Music Awards (2015)

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In another example of the wild style Miley Cyrus loves, this colorful ensemble is reminiscent of sugar candies, sunshine, and plenty of dazzle and glitter as she shines on stage during her performance.

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Z Lala - American Music Awards (2015)

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Some made fun of this fashion choice, and some thought it was executed genius. Either way, Z Lala’s Ursula-inspired AMA dress is as unforgettable as The Little Mermaid film itself.

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Cardi B - 2019 Grammy Awards

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Cardi B is known for zany looks and antics on the red carpet, but she really went outside her normal box with this memorable Grammy outfit. Classy and architecturally built like something of a soft ocean wave or clam with its pearl, Cardi stole the show in this one.

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Zendaya - Movie Premiere (2017)

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This 2017 look was fire for Zendaya, with a monarch wrapped pattern, understated makeup, and a slicked back hair bob right out of the 1920’s. But truly, when it comes to fashion, Zendaya can do no wrong.

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Uma Thurman - Oscars (2004)

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Uma Thurman’s red carpet ensemble in 2004 was not hers—or the Oscar’s—best, as it was something vaguely milkmaid inspired but not totally put together in a way that made sense to anyone.

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Nicki Minaj - Grammy Awards (2011)

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This leopard-laden fashion piece was one mixing French fashion techniques from over the centuries. From the high wig to the bubbled shape of the skirt to the leg prints connecting to the boots, this risk really paid off.

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Ellie Goulding - Halloween Costume (2014)

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Though she would be criticized many years later for cultural appropriation, at the time songstress Ellie Goulding donned this native fashion for a Halloween party, it was actually touted as one of the best of the year.

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Katy Perry - Met Gala (2019)

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While she now jokes about it being reminiscent of a Beauty and the Beast character, Katy Perry’s 2019 Met Gala look was an impressive feat and creation in fashion.

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Cameron Diaz - Oscars (2002)

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Looking fresh, beautiful, and in her own element at the 2002 Oscars, Cameron Diaz brilliantly pulled off this blushing floral dress that was a preview of the “Angel” she would later become.

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Billy Porter - Met Gala (2019)

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In another fashion piece that seemed to grace us from the (literal) heavens, Billy Porter won the 2019 Met Gala with this golden, Egyptian god-inspired outfit that took everyone’s breath away.

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Christina Aguilera - BAZAAR Icon Party (2018)

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In a dress that seemed to be inspired by Bjork’s 90’s swan dress, Christina Aguilera took it up a notch with 10 times the feathers, length, and white-blonde hair for a monocratic look.

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Gwyneth Paltrow - Oscars (2002)

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Velvet, stretch, tulle, smoky eye, and braids embodied 2000’s fashion to begin with, and so Gwyneth took that style and turned it into the ultimate glam look for the Oscars.

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Kendall Jenner - Much Music Awards (2014)

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Before she would become a multi-millionaire supermodel, Kendall Jenner was showing us her potential in this gorgeous, hand-beaded gown that portrayed a level of sophisticated fashion we’d never seen from her before.

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Ezra Miller - Premiere of Fantastic Beasts (2016)

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Ezra Miller is known for his eccentric fashion choices on the red carpet, and though this one was wildly dramatic, it didn’t translate positively to critics or viewers alike.

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Irina Shayk - Vanity Fair Oscar Party (2015)

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In a shadowy, sexy number that was structured just perfectly to her body and curves, model Irina Shayk looked stunning in her all-black gown at the 2015 Vanity Fair party.

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Lizzy Gardiner - Oscars (1995)

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No one can forget the Oscars dress that beat all others in the 90’s—the American Express dress worn by Lizzy Gardiner. Completely made by hand, it may have looked simple, but it was more complicated than getting approved for an AMEX.

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Kate Hudson - Oscars (2001)

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In a Dolly Parton look with sparkles, fringe, and beautiful ringlets, Kate Hudson’s beauty and fashion was clear even at the start of her career back in the early 2000’s.

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Whoopi Goldberg - Oscars (1993)

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With her first hosting gig on the Oscars, Whoopi decided to go all out in a blazing neon rainbow of glory with a dress-pantsuit hybrid. It was voted one of the worst Oscar fashion of all time.

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Faith Hill - Oscars (2002)

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Country superstar Faith Hill’s Oscar gown was reminiscent of a magical mermaid, mostly pink and sparkly, with a soft hombre of color change all the way down.

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Geena Davis - Oscars (1992)

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Touted as a mess of a dress, with critics comparing it to a bad Vegas wedding dress, Geena David was plenty comfortable in her Oscars fashion, but it didn’t go down in history.

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Joy Villa - Grammys (2015)

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We’re not quite sure how many soda and beer six-pack plastic holders had to go into the making of this dress, but it was for the taking of every fashion critic when Joy Villa wore this outfit to the 2015 Grammys.

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Angelina Jolie - Oscars (2000)

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Young, fresh-faced, and in love with Billy Bob Thornton and necklace vials of blood at this point in her career, Angelina Jolie opted for a simple, floor-length black dress and free-flowing hair, very reminiscent of Morticia or Elvira.

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Victoria Hervey - Golden Globes (2016)

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In a barely there ensemble, socialite Victoria Hervey turned heads per usual in her Gaurav Gupta designed black fashion number at the 2016 Golden Globes.

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Diane Keaton - Oscars (2004)

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This type of outfit is par for the course for icon Diane Keaton, though it was one of the first times the world saw that style of suit, gloves, and hat she would later come to give us all the time at red carpet events.

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Hilary Swank - Oscars (2003)

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2003 wasn’t sure what to make of Hilary Swank’s Oscar look. It was pretty, sure, but critics thought it looked like a cross between past season runway and senior prom.

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Leomie Anderson - BAZAAR Icons Party (2017)

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This designer and British model knows how to turn heads on the red carpet, as seen here in a beautifully bejeweled jumpsuit that’s sheer, classy, and beaded to perfection.

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Salma Hayek - Oscars (2018)

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Critics were split about this 2018 dress, but no one can argue that it seems to be the epitome of a modernized Roman look, with its layers, big diamonds, and magical hues of iridescence.

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Mariah Carey - BET Awards (2014)

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While Mariah Carey is normally above in pizazz with her glam and outfits, for this performance at the 2014 BET Awards, she kept the focus on her incredible voice, opting for a simple, yet elegant gown and gloves.

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Stacy Keibler - Oscars (2010)

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Looking like the Oscar statue herself in this gown, Stacy Keibler was one to watch in 2010, both in her modeling career and as the plus one on the arm of then-bachelor George Clooney.

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Amber Rose - MTV Video Music Awards (2014)

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In an outfit seemingly taken from Rose McGowan a decade before, Amber Rose would bare all in this chainmail, glittery ensemble that left little to the imagination.

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Kelly Ripa - Oscars (2018)

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In this gorgeous gown with a starburst train of surprise, America’s daytime sweetheart Kelly Ripa served class and fun at the 2018 Oscars in her Christian Siriano design.

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Toni Braxton - Grammy Awards (2001)

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This type of structure was a popular one in the early 2000’s, reminiscent of a Grecian woman warrior’s look from centuries past mythology. Toni Braxton pulled it off with so much class in this unforgettable dress.

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Kim Basinger - Oscars (1990)

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Kim Basinger’s whole Oscar look was unique, gorgeous, and memorable. She was nominated, she won, and she is remembered that year for more than just the dress—she was one of the first ever to use her speech to call out the award show.

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Selena Gomez - MTV Video Movie Awards (2013)

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Decked out in sheer red, gold, and jewels, Selena Gomez gave us a bold new look at her ever-evolving style and entertainment persona during her performance at the MTV awards in 2013.

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Courtney Love - Golden Globes (2000)

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Never one to leave her love of grunge, Courtney Love managed to keep the 90’s style but add plenty of glam to it for the 2000 Golden Globes.

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Scarlett Johansson - Met Gala (2018)

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This wine-hued dress was beautifully constructed and tailored perfect to Scarlett Johansson’s figure. It wasn’t the boldest of the 2018 Met Gala, but it was still a gorgeous gown.

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Heidi Klum - MTV Europe Music Awards (2012)

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It’s hard to think that anything looks bad on Heidi Klum, and this unique, handcrafted and hand-woven dress is no exception. From the stitched jewels to the tying of the dress to her body, it is a perfect ensemble.

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Susan Sarandon - Oscars (1996)

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Susan Sarandon is a force, and she always does what she wants—even if that means wearing casual sunglasses with her vintage, caramel colored silk gown at the 1996 Oscars.

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Pharrell Williams - Oscars (2014)

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California can get hot and there was no shame in Pharrell Williams’ game when he opted for cooler comfort in wearing tuxedo shorts on the red carpet.

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Jaimie Alexander - Thor Premiere (2013)

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It’s a style that’s been done before, but only few can really pull it off brilliantly, and Jamie Alexander is definitely one of them. There was never a more perfect dress to represent her character at the Thor premiere.

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Kate Peck - ARIA Awards (2014)

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Model Kate Peck was at the top of the worst dressed list in 2014 with this number that posed as something reminiscent of a dust bunny.

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Ashley Graham - MTV Video Music Awards (2016)

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Model Ashley Graham looks stunning in this see-through, glitz to the moon gown at the MTV awards in 2016. Always shattering the ceiling when it comes to fashion, she does not disappoint.

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Coco Rocha - Met Gala (2013)

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The Met called this Emanuel Ungaro designed ensemble the worst of 2013, and it’s not hard to see why. Dragonflies and cheetah seem to cause an eyesore.

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[NEXTPAGE]

Alicia Keys - MTV Video Music Awards (2001)

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In her first appearance after a hit single, Alicia Keys brought her New York persona and love to the red carpet, not shying away from loads of leather.

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Pamela Anderson - MTV Video Music Awards (1999)

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In probably the most well-remembered outfit besides her red Baywatch swimsuit, Pam Anderson showed up to the MTV awards with a pink furry hat that deserved its own award.

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[NEXTPAGE]

Tilda Swinton - Oscars (2008)

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Tilda Swinton has never been one for outrageous, overly done fashion or makeup, and in this velvet dress from the 2008 Oscars, she sticks to that preference, and she looks like a queen.

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[NEXTPAGE]

Blac Chyna - MTV Video Music Awards (2018)

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In a look that had been done, but with her own added flair, Blac Chyna broke out the glitz, glamour, and sexiness in this fringy bejeweled dress.

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