Princess Diana’s Best Fall Fashion Moments to Recreate

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.

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.

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

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

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.

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

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.