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Getty Images / Michael Stillwell
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Black sheep sweater
Kate Middleton and Meghan Markle aren’t the first royals to effectively send subtle messages through their fashion choices. In fact, their mother-in-law was a master at this. Worn by Diana on various occasions, this unmistakably warm and stunning sweater was believed to be a subtle tribute to her position in the royal family of the time.
Warm and wonderful women’s sheepskin sweater
Pants tucked into cowboy boots
Cowboy boots and pants aren’t two pieces you’d expect to go together, but Diana somehow nailed the trend in the ’80s and ’90s. And now that western style is starting to make a resurgence, the coming season couldn’t be a better time to dress up and dress up.
Oversized Check Blazer
Is it lined up for failure? Land erosion.
Oversized Blazer – Glenn Plaid
High waisted jeans with flaps
A high-waisted dress with feminine flats is a timeless combination, as Diana demonstrated during the school run in 1992.
Mango High Waist Straight Leg Mom Jeans in Dark Blue
Camel coat
If you need more convincing why you need a camel coat this fall, check out how gorgeous Diana looked in one in 1982.
A coat with an oversized belt in medium brown
Crewneck Sweatshirt
Leave it to Diana to keep casual sweaters looking chic. In the year While attending a polo match in 1988, the trend-setter wore a British Lung Foundation sweater with black blazers and a baseball cap, and jeans with cowboy boots.
British Lung Foundation Sweatshirt
Tennis shirt
If you need another reason to add this fall trend tennis sweater to your wardrobe.
Cable-knit sweater with cable knit
Sports collection
One of Lady D’s favorite looks in the ’90s consisted of a mix of oversized graphic sweaters, biker pants, work socks and dad sneakers. And two decades later, sports collections continue to be in fashion.
Princess Diana Diana Fly Virgin Atlantic Sweatshirt
Sweater with polished pants
Sure, a sweater and a pair of jeans will always be a classic fall outfit, but a sweater and pants combo will take your fall look to the next level of chic. Diana Pair your sweater with a white button down and ripped pants like she did in 1986.
Classic fit washed cotton poplin shirt
Wide Leg Pinstripe Pants in Deep Blue
Statement collar
Frilly, wide collars are synonymous with Princess Diana. She always opts for an oversized neckline – and it’s not hard to see why. Whether on a dress or shirt, prim and feminine embellishments add a touch of pizzazz to any simple outfit.
Printed statement collar
Contrast sweater
A white jumper with a contrasting color – like the one Diana is wearing in this photograph – is seriously stylish and will refresh any low-key look during the rainy season.
Saree contrast collar sweater in white w red
Sophie Dweck is the associate marketing editor for Town & Country, where she covers beauty, fashion, home and decor, and more.
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