Mary-Kate & Ashley Olsen’s Best Style Moments

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June 14, 2022 6:42PM EDT

Mary-Kate & Ashley Olsen have had many fantastic style moments over the years. Here are our favorites.

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Mary-Kate & Ashley Olsen’s Best Style Moments

Mary-Kate & Ashley Olsen’s Best Style Moments — From the time Mary-Kate and Ashley Olsen were little kids, they were always rocking outfits that had the public raving over their sense of style. The girls were always interested in fashion, but they decided to officially retire from acting in order to pursue careers in the fashion industry in 2012. The sisters actually founded their clothing line, The Row, back in 2006. The brand continued to build over the years, and in 2012, the sisters won the Womenswear Designer of the Year Award at the CFDA Awards for the first time. They would go on to win the honor again in 2015. Mary Kate and Ashlely also won Accessories Designer of the Year twice for the brand. Additionally, they founded the lifestyle brand, Elizabeth and James, as well as various retail collections. The twins’ style has been talked about for years, and we rounded up some of their fiercest fashion moments ever!

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Mary-Kate & Ashley Olsen In 1993

Mary-Kate & Ashley Olsen In 1993 — Mary-Kate and Ashley Olsen loved rocking matching outfits when they were younger. Here, they wore pink t-shirts and overalls while attending a convention in 1993.

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Mary-Kate & Ashley Olsen In 1996

Mary-Kate & Ashley Olsen In 1996 — Even as pre-teens, Mary-Kate and Ashley Olsen were super stylish. The sisters wore contrasting outfits while hitting the streets of NYC in 1996.

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Mary-Kate & Ashley Olsen At A Signing

Mary-Kate & Ashley Olsen At A Signing — Mary-Kate & Ashley Olsen are too cute in their matching, stylish hats while attending a video signing in 1996. They also both wore black dresses and matching, long necklaces.

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Mary-Kate & Ashley Olsen In Matching Outfits

Mary-Kate & Ashley Olsen In Matching Outfits — Mary-Kate and Ashley Olsen are all smiles while atending an event for ABC. They wore matching skirts, tops and cardigans in different colors, along with platform sandals.

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Mary-Kate & Ashley Olsen At The ‘Spiceworld’ Premiere

Mary-Kate & Ashley Olsen At The ‘Spiceworld’ Premiere — Mary-Kate and Ashley Olsen attend the ‘Spiceworld’ movie premiere. They wore matching velvet suits in different colors, along with their hair in updos.

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Mary-Kate & Ashley Olsen At The AmFar Gala

Mary-Kate & Ashley Olsen At The AmFar Gala — Mary-Kate & Ashley Olsen attend the amfAR Gala at the Cannes Film Festival in 2005. They showed off their very unique senses of style and different hair colors at the event.

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Mary-Kate & Ashley Olsen At A ‘Teen Vogue’ Party

Mary-Kate & Ashley Olsen At A ‘Teen Vogue’ Party — Mary-Kate & Ashley Olsen attend a party to celebrate one of their ‘Teen Vogue’ covers. The sisters wore very different outfits that were both fierce in their own way.

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Mary-Kate & Ashley Olsen At The WWD Gala

Mary-Kate & Ashley Olsen At The WWD Gala — Ashley Olsen and Mary-Kate Olsen attend the WWD 100 Anniversary Gala in New York City. They both wore black outfits and had matching hair to the 2010 event.

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Mary-Kate & Ashley Olsen At The Innovator of the Year Awards

Mary-Kate & Ashley Olsen At The Innovator of the Year Awards — Mary-Kate & Ashley Olsen attend the 2012 Innovator of the Year Awards. They both wore silk dresses, although they styled their hair differently for the event.

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Mary-Kate & Ashley Olsen At The CFDA Fashion Awards

Mary-Kate & Ashley Olsen At The CFDA Fashion Awards — Mary-Kate & Ashley Olsen attend the 2012 CFDA Awards, where they won the Womenswear Designer of the Year honor. Ashley wore a long pink gown, while Mary-Kate rocked all-black.

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Mary-Kate & Ashley Olsen At The 2018 Gala

Mary-Kate & Ashley Olsen At The 2018 Gala — Mary-Kate and Ashley Olsen attend the Youth America Grand Prix gala in April 2018. They wore matching dresses in different colors, with their hair in curls to the event.

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Mary-Kate & Ashley Olsen At The 2019 CFDA Awards

Mary-Kate & Ashley Olsen At The 2019 CFDA Awards — Ashley Olsen and Mary-Kate Olsen wear black dresses to the 2019 CFDA Awards in New York City. The girls began heavily favoring black outfits as they’ve gotten older.

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Mary-Kate & Ashley Olsen At A 2013 Event

Mary-Kate & Ashley Olsen At A 2013 Event — Ashley Olsen and Mary-Kate Olsen attend an event in Sweden in 2013. They proved that their business style is just as fierce as their red carpet looks, as they wore pants and sweaters to the event.

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Mary-Kate & Ashley Olsen At The 2014 Met Ball

Mary-Kate & Ashley Olsen At The 2014 Met Ball — Mary-Kate & Ashley Olsen attend the 2014 Met Gala in New York City. They both wore long, dramatic gowns with their hair pulled back.

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Mary-Kate & Ashley Olsen At The 2015 Met Gala

Mary-Kate & Ashley Olsen At The 2015 Met Gala — Mary-Kate Olsen and Ashley Olsen walk the glamorous red carpet at the 2015 Met Gala. They both wore long, black gowns with dramatic shoulders to the high-profile event.

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Mary-Kate & Ashley Olsen At The 2017 CFDA Awards

Mary-Kate & Ashley Olsen At The 2017 CFDA Awards — Ashley Olsen and Mary-Kate Olsen attend the CFDA Fashion Awards at the Hammerstein Ballroom In New York. Ashley wore a long black outfit, while Mary Kate rocked black pants and a white shirt.

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Mary-Kate & Ashley Olsen At The 2017 Met Gala

Mary-Kate & Ashley Olsen At The 2017 Met Gala — Mary-Kate & Ashley Olsen pose for photos at the 2017 Met Gala. They both wore intricately-designed outfits as they walked the famous Met steps for the red carpet.

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Mary-Kate & Ashley Olsen at the 2018 CFDA Fashion Awards

Mary-Kate & Ashley Olsen at the 2018 CFDA Fashion Awards — Mary-Kate Olsen and Ashley Olsen pose for photos at the 2018 CFDA Fashion Awards. The sisters wore black outfits and carried large purses as they walked the carpet together.

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Mary-Kate & Ashley Olsen At The 2018 Met Gala

Mary-Kate & Ashley Olsen At The 2018 Met Gala — Mary-Kate Olsen and Ashley Olsen show off their style at the 2018 Met Gala. They wore outfits for the Heavenly Bodies; Fashion & The Catholic Imagination theme.

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