14 Stylish Ways to Dress Like Princess Diana This Fall

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Princess Diana was one of the most influential style icons of the late 20th century—there's no doubt about it. From her record-setting wedding dress to that unforgettable LBD "Revenge Dress" and her many casual sweatshirt and biker shorts outfits, the late Princess of Wales knew how to take any ordinary piece of clothing and elevate it to another level, especially fall attire. Who could forget her statement-making sweaters, including that infamous black sheep pullover and "I'm a Luxury" crewneck? Or how about her many iconic blazers and high-rise mom jeans? The woman clearly knew how to dress.

Of course, those aren't the only trends that the royal pioneered. Here, a look at Diana's most legendary fall looks—and how to get her trendy style for the rest of autumn.

Black Sheep Sweater

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.

Warm & Wonderful Women's Sheep Sweater

Trousers Tucked in Cowboy Boots

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.

The Annie

Oversized Check Blazer

Plaid for fall? It's not entirely groundbreaking, but a checked print can make any autumn 'fit look polished and put together.

The Oversized Blazer - Glen Plaid

High-Waisted Jeans With Flats

High waisted denim with girly flats is a timeless pairing, as Diana demonstrated while on a school run in 1992.

Tate in Classic Blue

The Demi

Camel Coat

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.

More: Royal-Loved Coat Brands to Shop for Fall

Wool Coat With Handmade Belt

Crewneck Sweatshirt

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.

Princess Diana Sweatshirt

Tennis Sweater

Just in case you needed another reason to add an on-trend tennis sweater to your wardrobe this fall.

Malaine V-Neck Pullover - Tennis Whites

Sporty Ensemble

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. And more than two decades later, the sporty ensembles continue to be in fashion.

Princess Diana Sweatshirt

5" Airbrush High-Waist Biker Short

Rugby Striped Sweater

Stripes have long been a fashion staple for the royal family, especially for Diana. Here she is rocking a baby blue and pink top with white jeans and blue driving shoes in April 1997.

Pastel Striped Rugby Shirt

Breton Stripe Cardigan

Breton stripes were timeless then and their still timeless now.

Mini Marin Cardigan

Sweater With Polished Trousers

Sure, a sweater and a pair of jeans will always be a classic fall outfit, but the sweater-and-trouser combo will take your autumn look to next-level chic. Pair your knit over a white button down and pinstriped trousers as Diana did back in 1986.

Halle Crewneck Sweater

Classic-fit washed cotton poplin shirt

Tonelli Pinstripe Wool Blend Pants

Floral Sweater

You can't go wrong with a floral print. This cream sweater with blue and pink blooms looked lovely on Diana.

More: 21 Photos of Queen Elizabeth, Meghan Markle, and More Royals Wearing Florals

Amanda Sweaters

Statement Collar

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.

Bow-Detailed Ruffled Polka-Dot Silk Midi Dress

Texture to the Max

Princess Diana was clearly no stranger to playing with texture. Here she wore a printed dress with autumnal hues and cinched her waist with a brown leather belt and cap-toe flats.

Leona Dress

Textured square buckle belt

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