
Getty Images/Michael Stilwell
Advertising – Continue Reading Below
Black Sheep Sweater
Kate Middleton and Meghan Markle aren’t the first royals to artfully send subtle messages through their fashion choices. Worn many times by Princess Diana, this infamous Warm & Wonderful sweater was believed to subtly reflect her perceived status in the royal family at the time.
Warm & Wonderful Women’s Sheep Sweater
Trousers tucked into cowboy boots
Cowboy boots and trousers don’t look like much, but Diana was perfectly on trend throughout the ’80s and ’90s. And now that Western style has made a comeback, the coming season is the perfect time to wear it.
oversized check blazer
Checkered pattern for autumn? breakthrough.
Oversized Blazer – Glen Check
high waist jeans with flats
High-waisted denim and girly flats are a timeless combination, as Diana did for her school run in 1992.
MANGO High Waist Straight Leg Mom Jeans Dark Blue
camel coat
For more convincing reasons why you need a camel coat this fall, check out this elegant look Diana wore in 1982.
oversized belted coat medium brown
crew neck sweatshirt
Let Diana make a casual sweatshirt look chic. When attending a polo match in 1988, the trendsetter paired a British Lung Foundation sweatshirt with a black blazer and his baseball cap, and tucked jeans into his cowboy boots.
british lung foundation sweatshirt
tennis sweater
Just in case you need another reason to add a trending tennis sweater to your wardrobe this fall.
Marlene embroidered cable-knit sweater
sporty ensemble
One of Lady D’s favorite looks in the ’90s was an oversized graphic sweater paired with biker shorts, crew socks and chunky dad sneakers. And more than 20 years later, sporty ensembles are still in vogue.
Princess Diana Diana Fly Virgin Atlantic Sweatshirt
Sweater with polished pants
Sure, sweaters and jeans are always classic fall outfits, but the sweater and trousers combination takes your fall look to the next level of chic. Combine a knit over striped trousers.
Classic Fit Washed Cotton Poplin Shirt
Will Wide Leg Pinstripe Pants in Deep Blu
statement collar
The ruffled, wide collar was almost synonymous with Princess Diana. She always opted for an oversized neckline, and it’s not hard to see why. Add a touch of pizzazz to a dress with simple embellishments.
printed statement collar blouse
contrast sweater
A white jumper in contrasting shades, like the one Diana wore in this photo, is very stylish and refreshes the understated look for the breezy season.
Sarysu Contrast Color Sweater White W Red
Sophie Dweck is Town & Country’s Associate Shopping Editor, covering beauty, fashion, home and decor and more.
This content is created and maintained by a third party and has been imported into this page to allow users to provide their email addresses. More information about this and similar content may be found on piano.io.
Advertising – Continue Reading Below