Princess Diana’s timeless style transcends time. There’s always a fashion trend that harkens back to something the late royal wore, like opera gloves or biker shorts, which proves she was ahead of the curve when it came to what’s cool. To this day, many have tried to channel her classic style. Back in 2019, Hailey Bieber recreated a few of the royal’s outfits for Vogue Paris. Kate Middleton and Meghan Markle — both are married to Princess Di’s sons — continually reference her style in their looks. If you admire Princess Diana’s overall aura, her fall outfits, then, will provide plenty of inspiration for your own autumnal style.
Like you, she gravitated towards jeans, blazers, turtlenecks, cozy sweaters, and even sweats. The royal wasn’t afraid to step out in the most casual of outfits. However, even her most laid-back looks featured some kind of fashion twist. Take her iconic blazer, jeans, and sweatshirt look at the Polo Club in 1988 this (picture above), which she topped off with a cool baseball cap. Or her sweats ensemble, which she dressed it up by way of a blazer. No matter what the royal had on, every piece seamlessly worked together to achieve a cohesive “I’ve got this” energy.
Because she invested in the wardrobe essentials for fall, and then creatively paired them all together, her autumn outfits still stand the test of time today. Ahead, check out five of Princess Di’s best brisk weather-approved ensembles, along with some styling tips and shopping options. This season, all your autumnal looks will be royally fabulous.
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Blazer + White Top and Pants
The best way to break up your winter whites is with a few other neutral-colored pieces. Princess Di worked in a gray blazer, a brown belt, and brown loafers that had a patch of white to match back to her bottoms. A blazer is a fall necessity to have in your wardrobe as it not only instantly dresses up your outfit, but it also acts as the perfect transitional jacket. Meanwhile, white separates will always look chic for fall and winter.
Sweater + Polished Trousers
You might assume polished trousers are only for the office, but, here, Princess Diana shows they can easily work in an off-duty look, too. All you need is a casual sweater or warm pullover on top. The soft knit texture gives the sophisticated bottoms a more laid-back feel while you still look perfectly put together. You can skip the collared shirt underneath if it’s too fussy for you and swap the kitten heels for sneakers or boots.
Blazer + Sweatpants Set + Cowboy Boots
Princess Di demonstrated how to elevate your “I’m running errands outfit.” The blazer gave the sweatpants set a professional feel while the baseball cap added a touch of sportiness. The cowboy boots were unexpected (most people would opt for athletic sneakers) and added a western flair. Next time you’re about to run to the supermarket in sweats, make sure to dress up your look accordingly with the same pieces.
Cardigan + Midi Skirt
Instead of your usual cardigan and jeans combo, wear the layering staple with a flowing midi skirt for a bit of Parisian flair. Princess Diana channel nautical vibes with her navy striped cardigan, which she wore over a top and skirt look. The outfit is an easy one to wear for fall because it’s comfortable to move around in and utilizes layering, which is key to mastering transitional weather.
Sooner or later you’ll have to bring out the coats from the back of the closet. As soon as you look at Princess Diana’s dove gray coat, it immediately appears luxurious because of the black furry trim on the collar and sleeves. The color contrasting hue of the fur and coat is an instant eye-catcher and brings the necessary bit of detailing to her outerwear. Faux fur coats will be everywhere this fall, so invest in the style now.