Few have been able to capture the attention of the fashion industry, and beyond it, quite like the Olsen twins. They’ve surpassed child stardom and made a name for themselves thanks to their beloved brand, The Row. Yet, their popularity and intrigue persists—and the lack of access to their inner lives makes us want to know even more about them. As popular as the Margaux bag itself, the twins have cemented themselves as the North Star of the less-is-more approach, causing Olsen obsessives like myself to collect a potpourri of candid paparazzi shots and street style images, despite there not being many circulating.
Vogue’s Olsen Twin Style Guide:
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With winter quickly approaching, it’s time to dive into our favorite Olsen style photos for cold-weather outfit inspiration—after all, when I think of autumnal weather, I think of the Olsen twins. Their style is synonymous with the fall and winter season thanks to their affinity for larger-than-life layers: sumptuous coats, loose yet heavyweight trousers, and luxe knitwear.
As soon as the temperature dips below 50 degrees, I get dressed in the morning by asking, “What would Ashley Olsen do?” She would tuck her hair behind her ears and layer a tailored coat over a tailored button-up. On the weekend, when frigid air strikes, I ponder, “What would Mary-Kate wear to grab a latte?” She’d bring her slouchy carry-all bag and sport an equally languid pair of trousers, and probably top it all off with a great jacket.
For many, including us at Vogue, the Olsen twins—and this year’s recipients of the CFDA American Accessory Designer of the Year award—are a go-to for style inspiration. Take a closer a look and you’ll see that the trending items on our wish lists are also what makes up the foundation of their wardrobes, from smoking loafers and cashmere sweaters to tailored coats and black leggings. So, how can you embrace Olsen style this winter? Start with the basics, like a tailored coat from Tove or Victoria Beckham. Then, make sure to upgrade your button-up shirt collection with a striped option from The Frankie Shop or a pale blue piece from Toteme, which is always favored. Craving another minimalist must-have of theirs? Look to Everlane’s wide-leg trousers for an effortless pair, and sturdy combat boots from Aeyde or Gucci.
Below, the Olsen winter wardrobe starter pack featuring the pieces you’ll wear through the season, and after.
The Soft Ballet Flat
Although summer is ending, a universal footwear favorite is carrying over into the next season—the soft ballet flat. Flexible, comfortable, and versatile, there’s a wealth of options to choose from, from Gucci and The Row to Aeyde and Alaïa.
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The Ultra-Tailored Coat
Each season, a new tailoring trend emerges and takes over the outerwear market. The Olsens have always gravitated towards ultra-tailored coats that are crafted with precision. Look for blazer-like details like the ones in Gabriela Hearst’s double-breasted coat, or the sharp lines punctuating Victoria Beckham s double-faced overcoat. Ashley was seen this at this year’s CFDA ceremony in a similar long black style, with a rare vintage Cartier diamond brooch in the place of a where a pocket square might sit.
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The Poplin Shirt
This wouldn’t be an Olsen’s style guide without mention of button-down shirting. Both sisters have a vast arsenal of cotton poplin shirts—from tailored versions to oversized silhouettes. Toteme’s comes in clean, crisp blue, while The Frankie Shop’s and Khaite’s are cast in soothing stripes and creamy hues for minimalist-approved touch of color.
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The Top-Handle Carryall
The best top-handle bags vary in size and shape, but the Olsen’s often prefer a bowling silhouette that is big enough to store all daily essentials, and more. Coach’s Empire 40 bag made waves this year thanks to its vintage-inspired shape and roomy interior. For a new-now accessory, The Row’s Marlo bag is sure to become the next crowd-favorite.
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The Off-Duty Outfit
From classic crewnecks to baggy turtlenecks, cashmere sweaters can bring a comforting softness to any occasion, whether at the office or reading in the park. The Olsen’s l-o-v-e their knitwear, and are usually spotted in neutral hues with ribbed hemlines. To achieve their winter look, pair yours with elevated leggings—like stirrup styles or split-hems.
The Combat Boot
If knee-high boots are the perfect boot for evening’s out on the town, then the combat boot is the ideal footwear choice for relaxed weekends and errands. There are plenty of minimalist styles to channel their energy, like Miu Miu’s sleek lug sole, or Aeyde’s unfussy lace-up.
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The Slouchy Trouser
You’ll probably never spot Mary-Kate or Ashley wearing a fitted trouser—the two prioritise comfort above all else. For an affordable find, Cos’s are designed in a lightweight wool-blend twill, and tailored into a relaxed shape. Looking to make a big purchase? Kallmeyer and The Row have luxe wide-leg options you’ll own for decades.
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The Classic Loafer
Loafers, loafers, loafers! We can’t get enough. Whether they come in suede, leather, or in a chunky silhouette, the loafer has staying power. The Olsens prefer a classic silhouette, often wearing styles from The Row. But you don’t have to break the bank to achieve this winter vibe! Banana Republic has a patent leather pair and Madewell’s chocolate brown is croc-embossed.
The Winter White
Few things are quite as chic and effortless as a head-to-toe white. Maybe it’s the matchy-matchy aspect of it all, or the welcome challenge to survive the day without a stain, but we’re here for it and so are the Olsen twins. Go full steam ahead with a silky coat from Toteme, plus separates from Max Mara and Cos.
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The Modern Party Top
We’re still embracing the artful top in all its forms, from knitwear takes to silky evening-ready options. The best ones strike a balance between staple and investment, characterized by liquid-like textures. For an Olsen-approved tone on your next night out, look for soft fabrics and cape-like draping—we love the ones from Kallmeyer, Khaite, and naturally, The Row.
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