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Anna Wintour's big black sunglasses - The legendary Vogue editor finally explained that she wears those sunglasses because they hide her thoughts, plus they cover her tired eyes. She admitted that they may have become a crutch.

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Jackie O's pillbox hats - The former first lady was an icon of fashion and popularized this style of hat, often designed for her specifically by American fashion designers.

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Mr. T's chains - When it comes to creating a signature look, no one took so great a leap as Mr. T. 

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Sia's wig - What started as a way to distance herself from her past has become an iconic part of the artist's image. 

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John Lennon's specs - The Beatles member was rarely seen without his small circular glasses.

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Michael Jordan's hoop earring - The man was especially good at two things: sinking hoops, and wearing them.

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Michael Jackson's glove - The King of Pop first debuted a single white glove on stage in 1983, and it became a symbol by which he will be forever remembered.

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Elton John's starry shades - Elton John never shies away from a bold look, and he always pays special attention to his glasses. From rose-tinted shades to bedazzled frames, the singer's favorite accessory always steals the show.

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Kanye West's shutter shades - Long before Yeezy, and before becoming famous for the wrong reasons, West made those impractical shutter shades fly off the shelves.

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Karl Lagerfeld's motorcycle gloves - In addition to the white ponytail, tie, and shades, the motorcycle gloves became high fashion on Lagerfeld's hands.

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Tupac's bandana - The rapper's image became inextricably tied to this simple accessory, so much so that his wax figures will wear bandanas for the rest of eternity.

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Pee-wee Herman's bow tie - That tiny red bow tie will always be connected with Paul Reubens' iconic character.

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Gwen Stefani's bindi - When No Doubt broke out (in that era of misguided cultural appropriation), women everywhere started wearing track pants, crop tops, and bindis.

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Nelly's band-aid - It began as a basketball injury, but soon became the most famous band-aid of all time.

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Leonardo DiCaprio's newsboy cap - The actor loves to go incognito, but, ironically, his go-to choice for trying to remain unrecognized has also become his most well-known accessory.

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Johnny Depp's necklaces and colored shades - The number, kind, and color have varied, but the man loves his jewelry.

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Iris Apfel's black-rimmed glasses - The fashion icon is known for her bold and varied style, but the one accessory that's remained through the years are those enormous, black-rimmed glasses.

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Steve Jobs' sneakers - Besides his black turtleneck and jeans ensemble, Steve Jobs loved his New Balance shoes, which quickly went from dad sneakers to Silicon Valley keynote speakers.

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Rihanna's drinks - Whether it's a metal flask, a flask disguised as a bracelet, a clutch-flask, or just a flat out wine glass, it seems Rihanna's favorite way to finish an outfit is with a drink.

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Pharrell Williams' hat - When Pharrell first donned this strange, giant hat, no one knew if it was genius or ridiculous, which made it one of the most legendary moments in celeb fashion history.

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Slick Rick's eye patch - The rapper's eye was blinded when he was just an infant, but he took that accident and turned it into an iconic eye patch style that even pirates would envy.

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Coco Chanel's pearls - Rarely seen without long strings of pearls draped around her neck, the accessory became a symbol of her timeless style.

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Paul Newman's Rolex - Paul Newman's Rolex Daytona is considered by some to be the holy grail of timepieces. Gifted to him by Joanne Woodward, the watch sold for US$17.8 million at auction.

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Marilyn Monroe's fur shawl - Forget diamonds, Marilyn Monroe embodied Old Hollywood glamour best with her white fur shawl.

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Brigitte Bardot's bow - Along with her bigger-than-life hairdos, the French siren also popularized the once-girlish bow.

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Audrey Hepburn's black flats - The stylish star became cemented in history after she wore that famous little black Givenchy dress, but what never failed her both on- and off-screen were her simple black ballet flats.

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Grace Kelly's headband - The Hollywood actress turned Princess of Monaco created her polished look by sweeping her silky blonde hair back with a sophisticated headband.

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Jane Birkin's basket - Before there was the Birkin bag, Jane Birkin preferred a simple straw basket. 

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Samuel L. Jackson's Kangol hat -

The actor is rarely seen without his trusty Kangol hat, from casual outings to red carpet events. He even partnered with the brand on his own line!

On that note, find out why Samuel L. Jackson is the coolest man alive.

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