Mary-Kate and Ashley Olsen's best style moments

The most fashionable twins on the planet — Mary-Kate Olsen and Ashley Olsen — have parlayed their unique and iconic style sense into a $1 billion fashion empire. The actresses-turned-sartorial dynamos have been fronting fashion lines since they were teens and started their own couture label, The Row, in 2006. They’ve also been named womenswear designer of the year by the Council of Fashion Designers of America twice since 2012 and in 2019 took home the CFDA’s accessory designer of the year award for the second time in two years. To mark their 35th birthdays on June 13, 2021, is rounding up some of MK and Ashley’s most memorable fashion moments, starting with their 2019 Met Gala looks — complementary black leather ensembles by Chanel. Keep reading for more…

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Styling and matching since 1993! A then-7-year-old Mary-Kate Olsen and Ashley Olsen dressed to impress at an ABC TV Upfronts party in New York City in May 1993, rocking matching nautical-themed outfits and looking all sorts of adorable.

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At the 2011 CFDA Fashion Awards, Mary-Kate Olsen opted for a gorgeous black skirt by her couture brand, The Row, a glistening gold jacket by Chanel and strappy heels by Louis Vuitton. Ashley Olsen, on the other hand, wore a beautiful blue custom dress by The Row with heels by Manolo Blahnik.

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A knit beanie paired with formalwear? That should be filed under “things only Mary-Kate Olsen can pull off.” The slightly taller twin rocked a red crocheted beanie with a glamorous black gown for a boho-chic vibe at a Paris Fashion Week event in October 2006, while sister Ashley Olsen opted for something more Parisian-chic.

This pic goes way back — back before they adopted their famous pruning pose. A smiley Mary-Kate Olsen and Ashley Olsen went with bright prints for the “Charlie’s Angels 2” premiere in June 2003. Slightly older twin Ashley selected a brown-and-white floral halter dress while Mary-Kate went with a flowing, long-sleeved red-and-blue floor-length dress. MK had also darkened her blond hair at this point, setting the fraternal twins apart.

Surprise, surprise! At the 2019 CFDA Fashion Awards, Mary-Kate Olsen and Ashley Olsen donned their own label, The Row. The sisters — who took home the award for accessory designer of the year for their work on The Row that night — brought all the drama in head-to-toe black ensembles.

Layered up, blanketed in fur and clad in all black? It’s the Olsen twins trifecta! Ashley Olsen and Mary-Kate Olsen both have a major (and controversial) affinity for fur — and the look has provided them many an iconic red carpet moment, for better or for worse. When the two attended the WWD @ 100 Anniversary Gala in New York City in November 2010, they arrived in corresponding black fur jackets over monochromatic dark ensembles and incorporated three of their favorite fashion staples at once.

Mary-Kate Olsen and Ashley Olsen’s icon status was solidified in April 2004 when they received a star on the Hollywood Walk of Fame. For the occasion, the former “Full House” actresses wore feminine frocks and heels. Mary-Kate opted for a lovely lilac slip dress while Ashley stuck with one of her favorite hues in the form of a classic, crisp white dress.

The Olsen twins’ street style is almost more fascinating than their red carpet looks. Known for her eccentric layering, Mary-Kate Olsen’s vibe was often affectionately dubbed “homeless chic” in the early ’00s, while sister Ashley Olsen’s usual uniform was typically comprised of classic cuts and more feminine pieces. But both women share a deep love of the color black, oversized pieces — especially their sunglasses — as well as loading up on layers. For this Los Angeles coffee outing in August 2005, the twins showed off their massive shades and laid-back California style in layers and flip flops.

At the 2009 New York City premiere of the film “Nine,” Mary-Kate Olsen and Ashley Olsen looked — surprise! — incredibly stylish. Mary-Kate donned a colorfully woven jacket atop a black gown while Ashley chose an all-black-everything look with coordinating leather gloves, adding a pop of color with mustard yellow heels.

Layering is an Olsen twins specialty — so the unique outerwear they selected in January 2006 for a pre-Golden Globes party in Los Angeles elevated their looks to the next level. Ashley Olsen opted for a white minidress with a sleek leather coat over top, while Mary-Kate Olsen selected a dreamy green gown with a deep-V neckline and covered up with a fur stole. 

They love their oversized shades so much that sometimes they wear them on the red carpet! Though it’s usually a fashion faux pas, Mary-Kate Olsen and Ashley Olsen pulled off the look at the Broadway opening of “Lend Me A Tenor” in New York City in April 2010. Both were decked out in glamorous black gowns — MK’s frilled and Ashley’s sheer.

At the 2005 Cinema Against AIDS Gala in Mougins, France, Mary-Kate Olsen and Ashley Olsen sported some pretty atypical looks. Ashley went with a black floor-length dress that featured a plunging neckline, while Mary-Kate wore a pop of red in the form of a cropped jacket atop her cream-colored gown.

Ashley Olsen and Mary-Kate Olsen solidified themselves as fashion icons at the 2013 Met Gala in New York City. Ashley’s orange beaded Dior dress was stunning and made an entrance on its own. Her twin also went with beading, picking a Chanel drop-waist gown and covering it up with a quintessentially Mary-Kate fur-trimmed coat.

Occasionally, Mary-Kate Olsen and Ashley Olsen go back to their roots and decide to match. This happened at the 2015 Met Gala, where the glamorous twins showed up in corresponding dramatic black Dior gowns.

Pointy-toed flats were all the rage in the mid-’00s, and Mary-Kate Olsen and Ashley Olsen wore the trend while stopping by another ’00s staple — MTV’s “TRL” — in May 2004. Mary-Kate stole one of her sister’s signature colors and wore a white lacy dress with green pointy flats while Ashley took a page out of Mary-Kate’s book with a sleek black dress and silver flats.

Barely any black! Mary-Kate Olsen and Ashley Olsen almost completely ditched their signature shade at the 2017 Met Gala where they rocked gorgeous looks featuring a fabric we don’t often see on the twins — lace! Mary-Kate opted for a long-sleeved cream-colored lace gown with black bloomers underneath, while Ashley also rocked sheer lace, opting for off-white with black undergarments. When it came to accessories, Mary-Kate added a delicate headpiece while Ashley donned a colorful feather-embellished jacket.

Tulle and trains! At the 2010 ELLE Style Awards in February 2010, Mary-Kate Olsen and Ashley Olsen both stunned in super-glamorous gowns. Ashley slayed in a tan-and-blue Christian Lacroix dress while Mary-Kate stayed true to her sleek, dark style in a black Lanvin creation.

How adorable are they?! At the 2004 MTV Video Music Awards, Mary-Kate Olsen and Ashley Olsen looked boho chic in summertime dresses. Mary-Kate wore a strapless white frock with silver accessories while Ashley went for more color in a baby pink and orange spaghetti-strap dress.

Ashley goes dark! Mary-Kate Olsen and Ashley Olsen attended a Teen Vogue party in New York City in November 2006 with one twin sporting a drastically different look: Ashley rocked a slinky black gown to go with her new darker hair, while Mary-Kate opted for a surprising pop of color in a flowing red dress.

The twins know just how to use a corresponding accent color. At a dinner for The Row in New York City in October 2007, Mary-Kate Olsen and Ashley Olsen both went for all-black looks but incorporated a white accent — MK’s in the form of a white fur coat and Ashley’s via a white scarf.

Ashley Olsen and Mary-Kate Olsen attended the 2002 Vanity Fair Oscar Party in Beverly Hills as matching 15-year-old style mavens: Both donned sweet and simple black lace dresses and high-heeled sandals.

Though they’re known for never following the Met Gala’s theme, Mary-Kate Olsen and Ashley Olsen are always two of the most anticipated attendees at the annual event. In 2018, they didn’t disappoint, showing up in vintage Paco Rabanne pieces that showed the differences in their individual styles. Ashley’s caftan selection featured patchwork silk in warm copper, red and black shades, while Mary-Kate opted for a moonstone tunic necklace worn over a simple black dress from her own label, The Row.

We love the contrast here! At their Elizabeth and James line flagship store opening celebration in 2016, Mary-Kate Olsen and Ashley Olsen arrived looking ultra chic. Mary-Kate sported a signature oversized black look while Ashley opted for a chic cream coat. Everything was designed by the twins themselves!

Clad in their own designs, Mary-Kate Olsen and Ashley Olsen attended the 2012 CFDA Fashion Awards in June 2012. Their The Row gowns complemented one another, with Ashley donning a magenta-hued dress and Mary-Kate going for a sleek black number.

Black and gold is a classic Olsen combination. The pair wore the complementary colors at the 2008 Met Gala. Both were decked out in custom Diane Von Furstenberg that night: Mary-Kate Olsen rocked a glittery gold confection and Ashley Olsen showed a lot more skin than usual in a sexy black frock with side cut-outs.

Yin and yang! Ashley Olsen and Mary-Kate Olsen attended the Youth America Grand Prix’s Stars of Today Meet the Stars of Tomorrow Gala in New York City in April 2017 wearing these monochromatic looks. Ashley opted for a white frock with puffy sleeves while Mary-Kate stayed in her own lane, rocking a long-sleeved black design.

A cheetah coat? That hat? In a classic Mary-Kate Olsen moment, the fashion designer turned up at an event at the Museum of Modern Art in New York City in November 2009 wearing a glam animal-print coat over an all-black outfit with a dark lip, while her sister stayed true to her own style sense and rocked a feminine frilled blue-and-white dress.

Ashley Olsen and Mary-Kate Olsen complemented each other in different brown dresses at the premiere of their 2004 flick “New York Minute.” Mary-Kate paired her brown-and-white polka-dot frock with bright pink heels, while Ashley stayed classic with metallic stilettos to go with her silky chocolate brown dress.

Could they be any cuter? In 1999, Mary-Kate Olsen and Ashley Olsen went for coordinating looks while attending the Los Angeles premiere of “Anna and the King” — lilac and baby pink skirts with black buttoned-up cardigans.

Mary-Kate Olsen and Ashley Olsen made an elegant statement at the 2014 Met Gala in New York City. Both wore conservative, buttoned-up gowns with dramatic trains with their hair slicked back. Mary-Kate’s black vintage Ferre frock was both striped and sleeved, while Ashley’s navy blue Chanel dress featured gold button detailing.

Another year, another Met Gala. For the 2016 event in New York City, Ashley donned a beaded gold velvet coat atop a tan dress while Mary-Kate Olsen went for — no surprise here — a long black dress.

We’re fairly certain the Olsen twins are always cold, because they love themselves some coats and furs, sometimes combined. At the premiere of “Tower Heist” in October 2011, Mary-Kate Olsen combined their two loves with a black coat with fur over it, while Ashley Olsen opted for a neutral tan coat.

Back in 2002, Mary-Kate Olsen and Ashley Olsen went casual for the July 2002 premiere of “Austin Powers in Goldmember,” opting for matching sheer tanks complete with butterfly patterns and lace.

Ashley Olsen sported a chic menswear look while Mary-Kate Olsen rocked a minidress and tights at Free Arts NYC’s Seventh Annual Art and Photography Auction Benefit in 2006. The two even styled their hair in opposite fashions: Mary-Kate’s wild and down, Ashley’s twisted up.

Mary-Kate Olsen and Ashley Olsen stuck with complementary black and white on a trip to Stockholm in August 2013. Mary-Kate wore her usual all-black uniform, while Ashley provided a pop of white with her turtleneck.

This photo shows off the twins’ varied styles in 2004 with Mary-Kate Olsen rocking a quirky ensemble comprised of a long-sleeved black top, a pink skirt plus hot pink shoes and a clutch to match and Ashley Olsen keeping things equally conservative in a polka-dot blouse, white silk pants, gold heels and a brown bag.  

The Olsen twins love an oversized coat! The duo rocked one of their favorite staples at a Rolling Stones concert in Los Angeles in April 2013, with Mary-Kate Olsen opting for a half-up, half-down hairdo with her tan coat and Ashley Olsen picking a bright red velvet variety.

The twins are always so true to their individual style and we love it! Their red carpet appearance at the premiere of “The Union” in April 2011 is a clutch example — with Mary-Kate Olsen dressing perfectly out-of-the-box in a fiery orange Celine fur jacket paired with tangerine pants and patterned Louis Vuitton heels, and Ashley Olsen staying cool and conservative in a simple black Prada dress and understated Lanvin pumps.

Matching smiles and matching coats — it must be 2002! Mary-Kate Olsen and Ashley Olsen attended The Hollywood Reporter’s Annual Women in Entertainment: Power 100 Breakfast in Beverly Hills in December 2002 wearing matching corduroy coats. Ashley’s was tan and Mary-Kate’s was chocolate. Both toted black clutches at the event.

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