Getty Images/Michael Stillwell
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Black sheep sweater
Kate Middleton and Meghan Markle weren’t the first royals to expertly convey subtle messages through their fashion choices. In fact, her mother-in-law was a master at it. This infamous Warm & Wonderful sweater, which Diana wore on numerous occasions, was considered a subtle nod to her then-perceived place in the royal family.
Warm and wonderful sheep sweater for women
Pants tucked into cowboy boots
Cowboy boots and pants aren’t two pieces that you’d expect to go together, but Diana somehow nailed the trend perfectly in the ’80s and ’90s. And now that western style has resurged, the coming season couldn’t be a better time to take it on the go.
Oversized checked blazer
Throw for fall? groundbreaking.
The Oversized Blazer – Glen Plaid
High waist jeans and flat shoes
High-waisted jeans and girls’ flats are a timeless pairing, as Diana demonstrated at a 1992 school run.
MANGO high waist straight leg mom jeans in dark blue
camel coat
If you need even more conviction as to why you need a camel coat this fall, just look at how elegant Diana looked in a coat in 1982.
Oversized belted coat in medium brown
Crew neck sweatshirt
Leave it to Diana to make casual sweatshirts look chic. When the trendsetter attended a polo game in 1988, he wore a British Lung Foundation sweatshirt with a black blazer and baseball cap, and jeans tucked into cowboy boots.
British Lung Foundation sweatshirt
Tennis Sweater
Just in case you need another reason to add an on-trend tennis sweater to your wardrobe this fall.
Cable-knit sweater with Malaine embroidery
Sporty ensemble
One of Lady Di’s favorite looks in the ’90s was a mix of oversized graphic sweaters, biker shorts, crew socks and chunky dad sneakers. And more than two decades later, the sporty ensembles continue to be trendy.
Princess Diana Diana Fly Virgin Atlantic Sweatshirt
Sweater with polished pants
Sure, a sweater and jeans will always be a classic fall outfit, but the sweater and pants combo will take your fall look to the next level. Team your knit over white button-up trousers with pinstripes like Diana did in 1986.
Classic shirt in washed cotton poplin
Will wide leg pinstripe pants in deep blu
statement collar
Ruffles, 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 a blouse, the simple and feminine embellishment adds a touch of pizzazz to any simple dress.
Printed blouse with a statement collar
Contrast sweater
A white sweater with a contrasting hue – like the one Diana wore in this photo – is really stylish and will refresh any demure look during the fresh season.
Sarysu sweater with contrasting collar in white with red
Sophie Dweck is Deputy Buying Editor for Town & Country, where she covers beauty, fashion, home & decor and more.
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