Below, the Olsen winter wardrobe starter pack featuring the pieces you’ll wear through the season, and after.
REES, ULRA
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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Jamie McCarthy
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.
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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.
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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.
