Mary-Kate and Ashley Olsen – the trendsetters of street chic

Mary-Kate and Ashley Olsen – the trendsetters of street chic
Image: François Halard for The Row

From Hollywood to big fashion, from teen idols to acclaimed designers. Over the course of their career the Olsen sisters have gone through a few transformations both in their careers and their looks, but their iconic style status remained throughout. What started out as a cult of their on-screen presence has now turned into a loyal following of fashion enthusiasts.

We are tracing their fashion journey and deconstruct their simple but truly cult style.

Evolution of the Olsen sisters
Evolution of the Olsen sisters

Evolution of the Olsen sisters

Mary-Kate and Ashley’s career launched before they even uttered their first words, namely when these cherub-blonde twins landed their first film part at the tender age of nine months. In the series Full House, the twins played the same character and were even listed as one actor – Mary Kate Ashley Olsen - in the credits. The numerous acting contracts that followed this debut and the launch of their own production company set up by their banker father for his talented daughters made Mary-Kate and Ashley millionaires by the age of ten. At this point they dressed as any typical twins would with matching clothes that only slightly differed in colour.

The Olsen sisters style

The Olsen cult following grew over the years as they were changing and growing older. In the noughties, the twins swaped their iconic bobs with a fluffy fringe for long hair and a straight parting, opting for low rise trousers, open back tops and kitten heel sandals. Some of the main beauty trends of the time have clearly left their mark with their use of lip gloss and French manicure, not to mention the logomania. All of their looks at this time are accompanied by a Gucci or a Hermes bag with a large monogram, as well as straps and buckles, all of which show off a clear affeliation to one luxury brand or another.

The Olsen sisters style: black colour

It did not take long for boho style to take over these young women’s wardrobes. Mary-Kate and Ashley wrap their wrists with bracelets, purchase colourful floor-length dresses, pair flared jeans with fur coats and top it all off with lace elements, feathers and ruffles. And soon after the premiere of New York Minute (2004), their last film together (and, should we say, a total disaster), they move to New York where they start their student life and glam rock fashion takes over their wardrobes. They use thick dark eyeliner, wear bags with spikes and acquire matching leather jackets with black colour very much dominating their style and Balenciaga strap boots becoming a staple. We all saw what followed.

The Olsen sisters style: street chic

Street chic

Oversized sweaters, long skirts, wide trouser legs and torn jeans – this is how we have known the Olsen sisters for the past decade. It is difficult to believe that this effortless look was once a conscious fashion decision. When Mary-Kate was first spotted with her vintage Balenciaga City Bag, oversized sunglasses and voluminous clothes in neutral colours, The New York Times fashion experts immediately dubbed her the new icon of street chic style. Ashley was not too far behind. With her preference for more feminine and reserved items, she continued to wear dresses, chose cashmere sweaters over sweatshirts and actively used colour in her choice of accessories.

The Olsen sisters style: oversize


If there ever was an award for looking chic in oversized clothes, the Olsen sisters would have broken all the records. These petite young women can really pull off baggy coats and boyfriend style shirts. Their wide legged trousers and bags look like they can fit in all of their lifetime’s possessions and more. And yet, their silhouette never gets lost in these sizeless shapes and they do not look like they are drowning in the abundance of fabric. It must be something about the seamless cuts and quality of the materials they go for.

The Olsen sisters style: total black

Black colour

The Olsen sisters have done a great job at proving that black never gets out of fashion decade after decade. Known for not thinking seasonally about their wardrobe, they do not associate certain colours and items with winter or summer. They do not tend to opt for lighter and brighter colours as the days get sunnier but remain loyal to the total black look throughout the year. The colour is an essential companion in all of their social engagements. The sisters must be well aware that you just cannot go wrong with a black dress or suit.

The Olsen sisters style: comfortable shoes

Comfortable shoes

If you ever wondered where the trend for wearing flip flops in the city comes from, you have the Olsen sisters to thank for. They started wearing them daily and soon wore them as part of their gala dress code, much to the envy of those that would spend the evening enduring torturous stilettos. Mary-Kate and Ashley stick to being mobile and comfortable by wearing ballet pumps, loafers and shoes with a sturdy heel. But the one type of shoe they would never be caught in is trainers. Even when flying, the Olsens would much rather go for a combination of Birkenstocks and woollen socks than tie the laces on a pair of sporty shoes.


Mary-Kate and Ashley are skilled in avoiding paparazzi from a young age. This is where sunglasses come in handy. It is now such an inseparable part of the sisters’ style, that they keep them on even in the front row of a fashion show, just like Anna Wintour did.

The Olsen sisters style: sunglasses & boho

Boho jewellery

Not all of the Olsen’s fashion preferences are a thing of the past. Echoes of their boho period manifest themselves in the form of chunky jewellery, which complements their otherwise monochrome style. Large necklaces, pendants with bright tassels, gemstone rings and long earrings – all of these elements in the Olsen sisters’ style are as important as their oversized sunglasses.

The Olsen sisters: iconic hair style
Image: Dimitrios Kambouris/Getty Images

Iconic hair style

Mary-Kate has a rule of thumb: only using five hair clips or less for whatever hairstyle she goes for. Anything more is overdoing it, according to the celebrity hair stylist Mark Townsend who has been looking after the twins’ hair for more than 15 years. He says that the young women are so consumed by fashion and design that their hair often fades in comparison.

However, for an element of their look they do not want to spend too much time thinking about, their hair has become something of a distinctive feature. There are countless articles online on how to imitate their signature hairstyle and where there is demand, there is supply. In fact, there is nothing easier than recreating Ashley and Mary-Kate’s beach hair styling. All you need is dry shampoo, salt spray and a double curling iron.

The Row

It was not long until the Olsen sisters’ signature style would channel itself into its own clothing brand. Having moved away from acting and public life, the sisters took to what they have always loved: the business of fashion and design. And they did it like no one else. Moving away from popularising the brand through their own name, Mary-Kate and Ashley bet on the products themselves.

The Row by Olsen sisters
Image: @therow

By calling their brand The Row, named after London’s Seville Row – known as a destination for the best male suits – the twins sealed the cornerstones of their brand’s philosophy: perfect silhouettes and masculinity. Their debut product was a simple white T-shirt, a rare find for the age of glamour and velour that it launched in. Clients and fashion experts were quick to admire the new brand’s quality tailoring and materials. The pair celebrated their success in total anonymity. In the first three years of the company’s business, they have not given a single interview or revealed their affiliation with The Row.

The Row by Olsen sisters
Image: @therow

This tactic paid off and with time came recognition. The Council of Fashion Designers of America has referred to the Olsens as “designers of the year” on more than one occasion. The sisters’ work took a new turn in 2018, when the British fashion designer Phoebe Philo left Celine. As fans of intellectual fashion, luxury materials and seamless tailoring, the Olsens mourned the demise of one of their favourite brands and went all in with The Row. The brand found new fans in Zoe Kravitz, Gigi Hadid, Rosie Huntington-Whiteley and Margot Robbie. The accessories and shoes created by the twins became firm favourites in the lists of top everyday items.

Despite the rumours of The Row’s serious financial problems in 2020, the sisters are preparing for the next chapter. The brand’s future involves further development of their male collection, creation of new accessory hits and growth of their online sales. And it all seems to be going to plan.

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