Shop Princess Diana’s Best Fall Fashions

Getty Images/Michael Stillwell

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Black Sheep Sweater

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

Warm & Wonderful sheepskin sweater for women

Pants tucked into cowboy boots

Cowboy boots and pants 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 upcoming season couldn’t be a better time to wear it.

Checked oversized blazer

Plaid for fall? Innovative.

Oversized blazer – Prince of Wales

High Waisted Jeans with Flats

High-waisted denim with girly ballet flats is a timeless pair, as Diana demonstrated during a school run in 1992.

MANGO High waist straight mom jeans in dark blue

Camel coat

If you needed to know more about why you need a camel coat this fall, look at how stylish Diana looked in 1982.

Oversized belted coat in medium brown

Round neck sweatshirt

Leave it to Diana to make casual sweatshirts chic. While attending a polo match in 1988, the trend setter 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 a fashionable tennis sweater to your wardrobe this fall.

Malaine embroidered cable-knit sweater

Sporty set

One of Lady Di’s favorite looks from the 90s included a mix of oversized graphic sweaters, biker shorts, socks and chunky sneakers. And more than two decades later, sports ensembles continue to be in style.

Princess Diana Sweatshirt Diana Fly Virgin Atlantic

Sweater With Polished Pants

Sure, a sweater and a pair of jeans will always be a classic fall outfit, but the sweater and pants combo will take your fall look to the next chic level. Pair your knit with a white button and striped pants like Diana did in 1986.

Regular fit shirt in washed cotton poplin

Will Wide Leg Pinstripe Pants in Deep Blu

statement necklace

Wide, frilly collars were practically synonymous with Princess Diana. She’s always opted for an oversized neckline and it’s not hard to see why. Whether over a dress or a blouse, the refined and feminine adornment will add a touch of pizzazz to any simple dress.

Printed blouse with stand-up collar

Contrast sweater

A white sweater with a contrasting hue, like the one Diana wore in this photo, is super stylish and will refresh any understated look during the crisp season.

Sarysu Contrast Collar Sweater in White W Red

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