Celebrity Style: The Olsen Twins

The designer duo Mary-Kate and Ashley Olsen have been working since they were just 9 months old. Fast forward 29 years and the Olsen twins are celebrating their 30th birthday with a flourishing fashion empire, including their self-made labels The Row and Elizabeth and James. Starting out as child stars, the Olsen duo are now known in the industry as fierce fashion business women worth a combined fortune of over $100 million, and absolute style icons.

When it comes to their personal style, one thing is certain: Mary-Kate and Ashley Olsen are not shy of straying from modish trends. While an Olsen sighting is increasingly rare, when these women are in fact spotted it’ll be in bundles of cashmere and oversized slouchy pieces; their style has become notorious as a type of anti-paparazzi shield. Style workable all year round, Ashley and Mary-Kate have revolutionised women’s fashion and reinvented some long forgotten trends – cue the birkenstocks, slingbacks, bohemian dresses, and colourful scarves.

Over recent years, the Olsen’s have also become known for their love of menswear and masculine structuring; much of which features in their luxury collections. Evident in their style evolution, the Olsen twins can pull off anything – under the radar fashion figures to be admired. Keep reading to see some of the very best Olsen looks that anyone can recreate to look (and feel) as standout chic as these two do.


The Olsen sisters prove that head to toe black really is the easiest way to sleek styling. Dress up or down in flats or heels, the key to this look is through combining oversized slouchy pieces with structured ones. Tailoring is key: owing to their petit frames, these two knew fit before they knew fashion.


For a fierce everyday business look, pair black straight leg trousers with a button down shirt and an oversized trench coat. The key to avoiding looking swamped in any monochromatic outfit is to play with the textures and fabrics. As Ashley does here, try opting for a velvet or suede trench coat to separate the silhouette of the coat from the base layer, and choose a bag with a leather print. The Olsen’s love croc print and so do we. To really finish off the look, throw on some boots and a pair of black tinted sunglasses (Starbucks coffee is optional). OR be daring and try out a boxy style silhouette like Mary-Kate does here in her wide black trousers and oversized structured blazer. Instinct would normally tell you to keep the top fitted but instead Mary-Kate nails the look and chooses an even slouchier shirt in an off black hue. This overly masculine ensemble demands a strong shoe so follow in the Olsen’s footsteps and pair with a chunky brogue or loafer. Again, complete the outfit with black sunnies and a croc leather bag. For a more refined look, we can again look to the Olsen twins.

Ashley Olsen shows us how to do a formal all black outfit that is to die for. Simply swap out the loose trousers for a pair of cigarette style pants, the flats for pointed heeled pumps, and the oversized trench for a more fitted ankle length black coat in classic wool mix – fiercely feminine. Complete with large structured tote and loosely waved hair. 


From black to beige, the Olsen women also know exactly how to style lighter pieces for easy everyday wear, taking their style from bold and ballsy to delicate and dainty. How do they do it? The slingback. Often overlooked, the slingback has been back in the spotlight thanks to Mary-Kate and Ashley, and it instantly adds a soft feminine edge to any outfit.


Pair a crisp white shirt (a necessary staple in any woman’s wardrobe) with a knee length beige skirt for a really put together office look. Add a cool edge in a coloured slingback heel and keep the accessories monochrome and minimal. Take inspiration from Ashley if you want to pull off jeans at the office by teaming them with a thick oversized cosy coat and classic pair of slingbacks. Accessorise with a structured tote: the key to making jeans office wearable is to keep all other pieces sophisticated and classically structured. Voila – you’ve perfected the Olsen office-casual balance. For a look that you can take straight from office to bar, look no further than Mary-Kate’s black and camel combo. Opt for smart all black pieces underneath and mix formal trousers with a cashmere jumper.

Layer your neutrals with a statement camel coloured coat and an oversized nude scarf over the top for a chic and cosy look. Again, the black slingback heels are the key to making this outfit daywear appropriate bringing a laid-back vibe with the open back. They’ll also keep you from getting those dreaded heel blisters in the heat of summer.


Evidently masters of formal wear, Mary-Kate and Ashley Olsen also dominate in their overly casual off-duty looks. Scruffy has never looked so good.


Stepping out at the airport, Ashley shows us how to easily combine comfort with class in this cosy faux fur jacket. Scoring major style points, Ashley dares in a standout colour to contrast with the rest of her toned down outfit. With a statement coat you can get away with leggings or stretchy trousers to maximise your comfortability. Pair with some relaxed loafers or moccasins and add an unexpected pop with a black and white structured bag for your essentials. Even when stepping out with wet hair, Mary-Kate does it in style. For this super laid-back look all you’ll need is a pair of black skinnies, a slouchy black sweater, and some black loafers or toms. Team with a structured black bag and classic aviators to take this outfit from causal slob to causal sleek. This last look oozes carefree cool.

Who would have thought that tying your checked shirt round your front would look this good? This outfit is so simple yet quirky, and perfect to throw on for running errands during those colder months – all you need is a pair of leather loafers, cropped black skinny jeans, a checked shirt, and a chunky cream knit; cosy, practical, and unexpectedly stylish.


Not ones to follow fashion trends so much as start them, the Olsen twins have resurrected countless forgotten styles and made them relevant once again – although we have much to thank them for, we’ve narrowed it down to just 3 of their original style hits (a hard task we know).


First and foremost, the Olsen twins reshowed us how to use a chunky patterned scarf to finish off a simple jean and coat combo. To avoid the danger of looking frumpy, opt for a scarf with a cultural feel, as if it were a souvenir from a backpacker’s trip. The Olsen’s reignited our love for the scarf by either wearing it wrapped in a bundle as seen on Ashley here, or draped round the neck and hanging freely as seen in above photos. Never fearing to push the boundaries of fashion, Mary-Kate and Ashley also reminded us of the value of vintage pieces. In clashing vintage Dior and Chanel here, Mary-Kate’s choice of clothing was simply dismissed by many as ‘weird’. However, both of these women have reminded us not to let perceived fashion boundaries stop you from having fun with preloved pieces and looking a bit different and a bit quirky. The last reinvented trend is one that has been a bit of marmite fashion for years: the birkenstock sandal. The Olsen’s made these incredibly practical shoes stylish again and have been loyal to the birkenstock ever since. When paired – as Ashley does – with some boyfriend jeans and a button-down shirt, it’s not hard to see why they still cherish these simple slip-ons.

It would be justified to wonder exactly how the Olsen’s manage to keep their wardrobes so innovative, continually stepping out in fresh new looks. It can’t be as easy as they make it look. Or can it? We’ve put together some Olsen inspired outfits so you can effortlessly steal Mary-Kate and Ashley’s enviable style for yourselves.

To recreate this casual everyday look a la Olsen, try raiding the menswear section. Opt for this laid-back Abbie & Rose shirt in pale blue and team with a pair of relaxed boyfriend jeans and these Faguo tassel loafers to perfect the ‘I borrowed my boyfriend’s clothes and I nailed it’ vibe. Finish the outfit like Ashley with a quilted backpack and a pair of sunnies.OLSEN TWINS CASUAL STYLEPerhaps the chicest outfit Mary-Kate has ever stepped out in: here she shows us how to effortlessly pull off an oversized suit – something that even the most daring of fashionistas steer clear of. Try pairing the Antipodium culottes with this Lora Gene sat oversized trench coat, and tie the look together with croc leather accessories like the Meli Melo bag and Atalanta Weller heeled loafers.OLSEN TWINS ALL BLACK STYLEFor an Olsen inspired look perfect for any dinner date, opt for a black base in Sarah Sumfleth cigarette style pants and a black cashmere sweater. Layer with a Lora Gene trench coat and Lorenz Bach cashmere scarf in a complimentary neutral tone for sophisticated chic.OLSEN TWINS EVERYDAY CHIC STYLEA more casual look for an Olsen, channel Ashley’s cosy airport attire in Hoss Intropia leather leggings and an Ardent & Co faux fur cape. Grab this almost identical monochrome bag from Freedom of Animals while it’s still around and complete the look with some soft Duke & Dexter loafers.OLSEN TWINS OFF-DUTY STYLEWe hope you’ve loved these celebrities looks as much as we have!! Tag us @thenandnowshop in your own #OOTD photos and show us how you’ve channelled this formidable fashion twosome.