This 1999 Olsen Twins Look Still Holds Up In 2021

The most iconic style duo.

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NEW YORK, NEW YORK - MAY 06: Mary-Kate Olsen and Ashley Olsen attend The 2019 Met Gala Celebrating C...

Mary-Kate and Ashley Olsen are two of the most notable duos out there. From the early stages of their careers on the set of Full House to their roles in the fashion industry as influential designers behind the minimalist movement with their high-end label The Row, the Olsen twins have no doubt become household names in Hollywood and beyond. Of course, it would be remiss to say that a large part of that isn’t because of their sartorial decisions. Over the years, Mary-Kate and Ashley Olsen’s most iconic outfits have only gotten better — and there’s no doubt there will be more to come as time goes on.

Through every era of the Olsen twins’ style evolution, Mary-Kate and Ashley have always managed to create looks that, while indicative of the trends at the time, still hold up today. And yes, that includes the ensembles from the ‘90s and early aughts. Case in point: their coordinated cardigans and slip skirts from the premiere of Anna and the King in 1999 — a look that could easily be spotted on an it-Girl in 2021. They also championed iconic wardrobe staples like Balenciaga's City Bag, oversized sunglasses, and more recently, baggy yet structured pantsuits in neutral hues.

As they’ve gotten older, the famous sisters have streamlined their style into what it’s become known as today: timeless pieces with thoughtful tailoring, artistic draping, and luxurious materials. But, they still add bohemian details that defined their style of earlier decades, especially when it comes to jewelry. Their luxury label The Row has mirrored their style evolution and has earned the duo four CFDA Awards: American Womenswear Designer in 2015, and American Accessories Designer in 2014, 2018, and 2019.

There's plenty of inspiration to be had from fashion's most iconic duo, whether they're on the red carpet at the Met Gala or they’re simply taking a break outside of their NYC office. Scroll down to see how the Olsen twins’ style has evolved into what it is today.

New York City 2021

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In May 2021, Ashley stepped out in a pair of black leather slides, a longline trench coat, and dark flared trousers. Her look was yet another almost black monochrome moment save for her oversized cerulean blouse.

Longines Global Champions Tour Of Chantilly 2019

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Ashley went for an all-black look consisting of a dark button-up, silk skirt, and leather jacket tied around her waist. She relied on her maroon wide-brimmed hat for a pop of color.

Youth America Grand Prix Gala 2019

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The duo stuck to their signature black color palette at the Youth America Grand Prix's 20th Anniversary Gala in New York City. Mary-Kate contrasted her sleek coat and croc bag with a pair of red Manolo Blahnik kitten heels.

Met Gala 2019

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The Olsens donned head-to-toe leather for the 2019 Met Gala's "Camp: Notes on Fashion," putting an edgier spin on their classic style with leather gowns from Chanel.

Vanity Fair Party 2019

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Ashley walked the carpet at the Vanity Fair Oscars after-party in a floor-length belted black dress that she accessorized with strappy heeled sandals and a small envelope clutch.

Met Gala 2018

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The sisters embraced their love for flowing dresses at the 2018 Met Gala in dresses that combined their past and present senses of style. Ashley sported a colorful metallic gown by Paco Rabanne while Mary-Kate wore a gown by the Olsens' own line, The Row, over a Paco Rabanne tunic.

CFDA Awards 2018


Mary-Kate and Ashley proved their penchant for classic style at the 2018 CFDA Fashion Awards — where they won the award for Accessories Designers of the Year — wearing structured jackets and skirts. And of course, they finished off their look with top-notch accessories.

Met Gala 2017

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At the 2017 Met Gala, which highlighted Japanese designer Rei Kawakubo, the Olsens returned to their boho roots and wore lace dresses, which were accompanied by pops of color in the form of beads and fur.

CFDA Awards 2017

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The Olsens attended the 2017 CFDA Fashion Awards in outfits featuring qualities they maintain in their designs for The Row: timeless silhouettes, crisp tailoring, and neutral tones.

Met Gala 2016

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For their appearance at the 2016 Met Gala, which had the theme “Manus x Machina: Fashion In An Age Of Technology,” the designer duo stayed true to their personal style in sleek, neutral-hued floor-length dresses.

CFDA Awards 2015

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At the 2015 CFDA Fashion Awards — where the Olsens received another award for Womenswear Designers of the Year — the sisters each wore black silk ensembles, accessorizing with black clutches and white diamond jewelry.

At Work 2015

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In September 2015, the duo was spotted outside of their SoHo office. Mary-Kate's wide-leg pants and simple sweater were worn with flip-flops and layered necklaces. Ashley chose skinny jeans and a button-down, which she finished with taupe flats.

Met Gala 2015

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In 2015, the Olsen twins attended the event titled “China: Through the Looking Glass” while wearing coordinated vintage Dior by John Galliano gowns.

LAX 2015

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Arriving at LAX, the sisters showed off their polished yet cozy airport style. Mary-Kate wore a brocade coat, which she styled with black criss-cross slides and an oversized scarf. Ashley threw a gray pashmina over her shoulders, wore croc loafers, and carried an oversized black bag.

Met Gala 2014

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In 2014, Met Gala honored designer Charles James, who was known for his ballgowns. The Olsens paid homage to the designer with vintage gowns from Chanel and Gianfranco Ferré.

New York City 2013

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In April 2013, Ashley strolled around NYC in her signature black-on-black combination, this time with an added pop of color thanks to a blue croc bag slung over her shoulder.

Met Gala 2013

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In 2013, Ashley got creative with the Met Gala's “PUNK: Chaos to Couture” theme by choosing a floaty vintage Dior dress for the occasion.

Met Gala 2013

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For the 2013 Met Gala theme, “PUNK: Chaos to Couture,” Mary-Kate dipped into her extensive vintage collection. She wore a drop-waist dress by Chanel, which she styled with an embroidered silk robe layered on top. She finished off with bohemian accessories, including layered necklaces and crystal earrings.

Met Gala 2012

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In 2012, Mary-Kate attended the Met Gala solo. For the year's “Schiaparelli and Prada: Impossible Conversations” theme, she chose a black draped gown from The Row and a metal clutch.

LAX 2012

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Ashley touched down in Los Angeles wearing an ensemble true to her classic style. She layered a cozy brown coat over black skinny jeans and finished off with two-tone flats.

CFDA Awards 2012

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The Olsens received the Womenswear Designers of the Year Award at the 2012 CFDA Awards for their minimalist fashion brand, The Row. Both sisters wore sleek dresses and carried classic handbags to the ceremony.

Met Gala 2011

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For 2011's Met Gala theme titled “Alexander McQueen: Savage Beauty,” Mary-Kate chose a sweeping red Givenchy gown.

Met Gala 2011

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Ashley chose a monochromatic look for the evening, wearing a black Dior gown with billowing white sleeves.

Lincoln Center 2011

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Ashley exited a car at Lincoln center in a texture black dress and pumps. She wrapped herself in an ink green furry stole for a pop of color.

Met Gala 2009

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For 2009's Met Gala, which was themed “The Model As Muse,” Ashley attended with then boyfriend Justin Bartha. She chose a white gown from her label The Row complete with long sleeves and an open back.

Met Gala 2009

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Mary-Kate opted for a vintage look on the red carpet, donning a silver and tiered gown by Christian Lacroix.

Chanel 2008

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The duo sat front row at Chanel's 2008 fashion show, both wearing YSL's signature oversized sunglasses. Mary-Kate opted for leather leggings, a gray sweater, and tan platform sandals. Ashley chose a white Chanel coat with black tights and booties.

Met Gala 2008

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At the 2008 Met Gala, which was themed “Superheroes: Fashion and Fantasy,” the pair took on sleek silhouettes. Both sisters wore gowns by Diane von Furstenberg and heels by Christian Louboutin (who accompanied them for the evening).

Dior Fashion Show 2007

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Ashley and Mary-Kate sat front row at the Dior fashion show in Paris. Mary-Kate chose a black ball gown, which she contrasted with a red knit beret. Ashley chose a furry white coat, black tights, and black heels.

Met Gala 2007

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The 2007 Met Gala theme was “Poiret: King of Fashion” — an ode to French designer Paul Poiret. Ashley chose a Grecian white column gown, which she belted with a thick patent waist belt.

Met Gala 2007

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This dramatic gown, a design from Lily Et Cie by Rita Warnick, was a dramatic choice by Mary-Kate for the 2007 Met Gala.

Pre-Golden Globes Reception 2007

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Ashley and Mary-Kate channeled old Hollywood glamour at a party at LA's iconic Chateau Marmont. Though both wore a bold red lip, Ashley kept the rest of her look neutral while Mary-Kate chose an emerald gown.

Paris 2006

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In October 2006, Mary-Kate entered the Ritz Hotel in Paris dressed in a punk outfit that included knee-high leather boots and an Alexander McQueen skull print scarf.

Met Gala 2006

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For the Anglomania-themed event, Mary-Kate chose a black dress with lace sleeves by Badgley Mischka. Ashley also wore the designer to the event. "These were custom looks, so we went through fabrics together and they gave us an idea of what they liked," designers Mark Badgley and James Mischka told Page Six in 2018. "This was around the time that they were always photographed running around with their Starbucks, so it was fun to glam them up."

CFDA Awards 2006

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For the 2006 CFDA Awards in New York City, both Ashley and Mary-Kate chose colorful floor-length gowns.

amfAR Gala 2005

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For this 2005 amfAR gala at the Le Moulins de Mougins in France, the twins went back to wearing bohemian-inspired ensembles with long, flowing (and in the case of Mary-Kate, tiered) dresses.

Met Gala 2005

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For 2005's “The House Of Chanel” Met Gala, the sisters got creative. Mary-Kate continued to channel her bohemian style with a floor-length vintage white cotton dress and layered jewelry. Ashley chose a gold high-low dress from Oscar de la Renta.

Marc Jacobs 2004

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In September 2014, the duo attended Marc Jacobs' fashion show in New York City. Ashley chose a more classic look consisting of blue jeans and a white button-down. Meanwhile, Mary-Kate went for an outfit with an unexpected color combo: pink and green.

Hollywood Walk Of Fame 2004

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To receive the honor of having a star on Hollywood's iconic Walk of Fame, Mary-Kate and Ashley went for more classic ensembles. However, both outfits carried free-spirited notes that were reminiscent of their go-to boho style.

Vanity Fair Party 2004

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For a night out in New York at the Tribeca Film Festival's Vanity Fair party, the sisters chose polished yet playful ensembles. Ashley chose a polka dot top with wide-leg pants, accessorizing with an orange clutch and green pumps. Mary-Kate kept to a black and pink theme.

Tribeca Film Festival 2004

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The duo walked the red carpet at the Tribeca Film Festival in New York City while wearing coordinated brown outfits.

Kids' Choice Awards 2004

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The sisters walked the orange carpet for Nickelodeon's 2004 Kids’ Choice Awards in looks that while all their own, still managed to be coordinated. Mary-Kate accessorized a deep blue dress with oversized turquoise earrings, jelly bracelets, and gold gladiator sandals. Ashley went for a more streamlined look with a striped halter, brown silky trousers, and gold strappy heels.

Fox Sports Grill Opening California 2003

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At the opening of Fox Sports Grill in Irvine, CA the sisters opted for coordinated looks that included baby doll tops, flared jeans, and ballerina-style flats. Mary-Kate layered up the look by adding a blazer, scarf, and printed hat.

Charlie's Angels: Full Throttle Premiere 2003

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The Charlie’s Angels: Full Throttle premiere is where the two sisters showed their love for the bohemian style. Ashley wore a tropical-inspired floral print dress while Mary-Kate donned a flowing kaftan dress.

Album Release 2001

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The Olsens embraced the trend of low-rise bottoms for the album release party celebrating NSYNC's "Celebrity" in 2001.

Anna And The King Premiere 1999

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Mary-Kate and Ashley wore coordinated ensembles for a similar-but-different look to the Anna and the King premiere in 2000. The pair sported fitted cardigans with slip skirts and strappy sandals, an outfit that's still on-trend today.

Arm and Hammer Museum 1998

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The twins went for a red and blue, almost twinning moment in their coordinating slip dresses with floral prints, lace panels, and velvet swatches. Plus, the pair wore chunky heels that would fit right in with 2021’s platform shoes trend.

Spice World Premiere 1998

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The sisters wore coordinated looks to the premiere of Spice World in 1998. The shiny blazers and piece-y updos were peak '90s style.

It Takes Two Premiere 1995

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For their premiere of It Takes Two, the Olsens wore coordinated skirt sets with Mary-Janes.

12th Annual VSDA Convention 1993

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At the 12th annual VSDA convention in 1991, the young stars made an appearance in matching outfits featuring denim overall dresses, red button-down tank tops, and bandanas as hair accessories.

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