14 of Princess Diana's Best Fall Fashion Moments—and How to Recreate Them in 2026

Camel Coat

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If you needed any more convincing as to why you need a camel coat this fall, just look at how elegant Diana looked in one in 1982.

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Winter White

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The key to wearing white as the temperatures drop? By pairing it with touches of brown as Diana did here.

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Trousers Tucked in Cowboy Boots

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Cowboy boots and trousers aren't two pieces you'd expect to go together, but Diana somehow executed the trend perfectly throughout the '80s and'90s. And now that western style has made its resurgence, the coming season couldn't be a better time to wear it out and about.

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Oversized Check Blazer

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Plaid for fall? It may not be entirely groundbreaking, but a checked print can make any autumn outfit look polished and put together.

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Sporty Ensemble

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One of Lady Di's favorite looks during the '90s included a mix of oversized graphic sweaters, biker shorts, crew socks, and chunky dad sneakers. The ensemble is perfect for the early days of fall.

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Tartan

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Is it really royal fall fashion moment without a bit of tartan? Princess Diana looked seasonally appropriate in a blazer featuring the pattern.

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Statement Collar

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Frilly, wide collars were practically synonymous with Princess Diana. She always opted for an oversized neckline—and it's not hard to see why. Whether it's on a dress or blouse, the prim and feminine adornment will add a touch of pizzaz to any simple dress.

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Plaid Bomber Jacket

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One can never have too much plaid in their fall wardrobe, as proven by Princess Diana. For gloomy days, consider adding a checked bomber jacket to your collection, similar to the one she wore here.

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Black Sheep Sweater

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Kate Middleton and Meghan Markle weren't the first royals to expertly send subtle messages through their fashion choices. In fact, their mother-in-law was a master at it. This infamous Warm & Wonderful sweater that Diana wore on numerous occasions was believed to be a subtle nod to her perceived place in the royal family at the time.

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Crewneck Sweatshirt

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Leave it to Diana to make casual sweatshirts look chic. While attending a polo game in 1988, the trendsetter wore a British Lung Foundation sweatshirt with a black blazer and baseball cap, and jeans tucked into cowboy boots.

Sophie Dweck is the Shopping Editor for Town & Country, where she covers all things fashion, beauty and lifestyle, shares her expertise on the most worthwhile luxury products, tests and writes in-depth reviews on the very best essentials worth investing in, as well breaking news about the latest launches, and of course, reports on the biggest sales and deals to shop no matter the day. Some of her favorite items to date are Gwyneth Paltrow's ski trial cardigan, the Hotel Chocolat Velvetiser, and ZIIP’s microcurrent device. When Sophie isn't testing state-of-the art beauty tech or breaking down TikTok aesthetics, she loves indulging in BonBon sweets (Sorbisars, for the win!) and finding the next trend before it goes viral.

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