The Best Kim Kardashian Outfits Over The Decades (& What She Says Is Her Worst)

No matter who you are — whether you’re an everyday fashion lover or one of Hollywood’s elite members — you’re bound to have a few sartorial moments you wish had never happened. But like any other part of life, it’s all about the journey — and Kim Kardashian knows that. As one of the biggest names in the industry and one who never backs down from a fashion moment, the 39-year-old entrepreneur has taken plenty of fashion risks. Sure, the A-list celebrity has noted some of these looks as her worst ever, but they’ve also led to the best Kim Kardashian outfits yet. And by the looks of her latest ensembles, they’re only getting better with time.

Looking through some of her most iconic outfits to date, Kardashian took a walk down fashion memory lane in VOGUE’s video series, “Life in Looks.” Reminiscing about now-famous outfits, including her all-over floral print dress from the 2013 Met Gala, the celebrity went through the ups and downs of her fashion choices. Through all of her show-stopping looks though, the SKIMS founder deemed one ensemble from an UsWeekly party in 2006 as her “worst look of life.” The outfit featured a gray sweater dress layered over a white button-down shirt, along with designer accessories. “I was able to afford a Fendi belt and matching Fendi boots,” Kardashian shared in the video. But while the style icon considers this outfit to be her worst, it also paved the way to the undoubtedly chic looks she’s known for today.

Click through to take a look at Kardashian’s fashion journey and her best looks through the years.



In a simple black dress with ruffled details and coordinating peep-toe pumps, Kardashian proves that a classic LBD will never go out of style.

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In 2007, the future entrepreneur opted for a form-fitting dress with lace details.

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In another black dress in 2008, Kardashian opted for a style featuring a bubble hem and a feminine, square neckline.

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For the 2009 Emmys, the second oldest Kardashian sister took a sophisticated approach to her look in a sleek, one-shoulder white gown with hoop earrings.

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At the 2011 Grammy Awards, Kardashian took a route that teemed with '70s glamour with a sparkling gold dress and voluminous waves.

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For her appearance on The Tonight Show with Jay Leno in 2012, the Keeping Up With The Kardashians star wore a spring-ready flower-embellished dress.

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You can't talk about Kardashian's best outfits without discussing her floral print Givenchy dress from the 2013 Met Gala. Complete with matching gloves, this is one ensemble that'll go down in red carpet history.

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2014 is the year the A-lister started to show off her affinity for neutrals, with a strapless beige suede dress, matching pumps and a black coat.

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As the Kardashian-Jenners jaunted around Paris to celebrate Kim and Kanye's nuptials, the mogul sported an array of looks (previous ensemble, included) but this ornate dress from Balmain was the catalyst of the entire weekend.

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Giving her maternity style a sleek take in 2015, Kardashian wore a simple black dress with lace-up details and accessorized with strappy sandals.

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Opting for a glowing beauty look, Kardashian complimented the natural makeup with a simple lingerie-style slip dress and matching white satin robe.

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Kardashian continued to serve looks while out in Paris during fashion week in 2016, stunning in a gold sequined Balmain dress, PVC Yeezy pumps, and an iconic Cher-inspired middle part.



Kardashian chose to wear a menswear-inspired ensemble with a coordinating suit and minimalist sandals at LACMA's 2017 Art + Film Gala.

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Mastering the blazer-dress trend, Kim paired her icy-blonde hair with a tailored mini that was both polished and sexy.

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2018 marked the beginning of Kim Kardashian's deep dive into the fashion archives. Citing Naomi Campbell as one of her biggest inspiration, the mom-of-four was putting her own modern spin on some of Versace's most popular designs.



In 2018, Kardashian sparked headlines for a sheer, graphic vintage Jean Paul Gaultier dress at the E! People's Choice Awards.

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Kim Kardashian's head-to-toe leopard print look from Azzedine Aläia during Paris Fashion week was truly iconic — from the ultra-glam beauty look and Old Hollywood curls, the overall feel of the outfit was executed seamlessly.



Showing off her ultra-toned body, Kardashian sported a vintage gown by Mugler while attending the 5th Annual Hollywood Beauty Awards in Los Angeles.



Showing off (yet another) Mugler dress from the archives, the beauty mogul attended New York Fashion Week.

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2019 carried a lot of notable looks for the Kardashian, but it was perhaps her Mugler ensemble from the year's Met Gala that stole the show, with its glamorous "wet" look.

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The year has hardly started to settle in, but 2020 is proving to be one of Kim Kardashian's best fashion years to date. For Paris Fashion Week, the entrepreneur donned a straight-off-the-runway ensemble from Balmain.

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Kardashian may have noted this look to be her "worst look of life," but the oversized belt and knee-high boots feel entirely on-point with the trends of the early-aughts era making it a stylish option of the time.

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