All Of The Olsen Twins' Best Street Style Moments

Take style cues from the world’s most stylish twins

Mary-Kate and Ashley Olsen
Photo: Getty

No one does the art of effortless styling as much as the Olsen twins, Mary-Kate and Ashley do.  The duo has come a long way since they first graced our screens in 1998, moving from child stars to current fashion moguls of award winning fashion label, The Row. The stylish duo’s current signature look of sweeping hemlines, boxy proportions, and black on more black, has inspired various fan accounts and style blogs in its wake, showing just how they are still every bit as relevant as they were a decade ago.

We track the best street style moments that have graced our eyes since their fashion careers. Scroll ahead for some seriously chic inspiration.

2019

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Our favourite style icons wore matching birthday gown tiaras made of 40-karat white gold diamonds for a birthday celebration dinner in Manhattan. A departure from their usual lowkey looks, but every bit as tasteful as birthday girl tiaras can be in the hands of the best accessories designers in America.

2019

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The twins in their signature all black ensemble outside their office in New York.

2018

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On the way to the 2018 CFDA Fashion Awards, decked in head to toe The Row.

2018

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Ashley leaving her office in New York, in a loose fitting maxi dress, structured boots, and a boho scarf.

2018

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Ashley makes a statement in this Céline Pre-Fall 2018 coat  paired with trousers and brown Nike Cortez.

2018

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Mary-Kate wearing The Row menswear.

2018

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Mary-Kate in pinstripe top and bottom, and white aviators.

2017

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Ashley at the Beverly Hills Hotel.

Related article: 10 Of The Most Successful Celebrity Fashion Lines

2016

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Mary-Kate and Ashley at their Elizabeth & James store opening in Los Angeles

2016

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The clog was the ugly-pretty shoes of 2016. Here, Ashley turns it into a chic statement piece with boyfriend jeans, tailored jacket and ladylike purse which lent the look a sense of poise.

2016

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Mary Kate was spotted during a coffee run in New York in a monochrome look with a chic bun and wide legged pants.

2016

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The twins both touted alligator skin bags from their label, The Row, while out in Manhattan, New York.

2014

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Mary Kate and Ashley out for a coffee run in NYC

2014

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Take notes on comfy airport fashion from the twins, who sported matching baggy outerwear, and black birkenstocks over socks.

2014

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Mary-Kate and Ashley out in New York City either before or after the Anna Wintour Costume Center opening at the Metropolitan Museum of Art. Mary-Kate is dressed in a skirt by The Row, Lace up sandals by Christian Louboutin, and Ashley in a dress by The Row and a kitten slingback by Stuart Weitzman.

2013

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The perfect black on black combo on Ashley, and the best fit slouchy jeans we’ve ever seen in Mary Kate.

Related article: Best Designer Bags To Invest In, According To Fashion Editors

2012

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Mary Kate and Ashley spotted before or after The Fresh Air Funds Salute to American Heroes. Mary Kate wears The Row top, skirt and bag, with Fendi shoes, and Ashley wears The Row ivory dress, Manolo Blahnik shoes and a Sidney Garber bracelet.

2012

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Mary Kate spotted in New York’s meatpacking district in a menswear inspired tailored outfit, wearing brogues and a Mulberry bag.

2011

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Ashley Olsen in the Birkenstock Gizeh sandals, with denim and an oversized blue button down shirt.

2011

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Ashley wearing The Row’s Dolman Sleeve top in grey and a pair of red Chanel kitten heels.

2011

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The twins after a coffee run at the Upper East Side

2008

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Ashley heading to a Letterman appearance

2007

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Mary-Kate leaving an event in a white dress and Christian Louboutin heels

Related article: Red Alert: Christian Louboutin Beauty Is Coming To Singapore

2007

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The twins after a Chanel show

2006

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The twins seen leaving the Met Gala in Badgley Mischka


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