Princess Diana has been gone for more than two decades, but we still cannot get enough of her. As a philanthropist, a truly empathetic humanitarian, a beloved mother and arguably the most popular member of the royal family in her time, her influence remains. And let’s not forget her fashion, oh my word. She was a true original, perhaps especially when it came to her fall wardrobe. There is just something about fall fashion that seemed to suit the Princess of Wales as right as rain.
Whether she was wearing jeans and boots, fun sweaters, blazers, or dressing up for a formal event, Princess Diana really knew how to get the most out of temperate fall weather. Even as young Lady Diana Spencer, she knew how to pull together a perfect fall look.
Princess Diana’s status as a fashion icon really started to take root in the early days of her courtship with Prince Charles when she was just 19 years old. Back then, she was a fresh-faced nursery school teacher living with her flatmates and sticking to a fall wardrobe of cords and sweater sets and a sweet smile. She stayed true to her roots, especially when the weather turned cool and the leaves turned color. She knew what looked good and she knew what she liked and really, what else is there?
How It Started
Back when she was just a young girl in 1971, Lady Diana Spencer already knew how to make the most of a cool Annie Hall-esque floppy hat for fall. She paired the wide-brimmed black hat with a simple tunic top, long blonde hair and weirdly perfect bangs. Also a direct look that said she knew she looked good, and truly that confidence is kind of amazing.
A Royal Purple Sweater Vest
Princess Diana wore a purple sweater vest over a collared shirt to her job as a part-time kindergarten teacher in London. She also wore a look of deep disdain for photographers that paired well with her royal purple sweater vest in my opinion.
High End Rubber Boots, Thanks To Diana
Princess Diana’s engagement photo shoot with Prince Charles at Balmoral Estate in Scotland gave us one of her most iconic fall looks; cords, bright sweater, turtleneck, and green rubber boots with socks. A future princess, showing us how it’s done.
Monochromatic Checks Look Good
When Prince Charles and Princess Diana were at Balmoral in Scotland, she even managed to make a neutral checked loose coat and skirt combo look good. It’s all about the details with her.
Cardigans & Button Downs All Around
Princess Diana’s cardigan and button down shirt combination, coupled with a patterned bag and slim pants, is the epitome of easy fall fashion. Also her hair is incomparable, I’m just saying.
New Mom In Red Boots
Princess Diana’s boot collection is truly the stuff of legends, and pairing these red boots with a matching red belt along with a cream pleated skirt and sweater? Genius. Also baby Prince William looks cute too.
School Drop-Off Chic
Loose pants tucked into boots, a baseball cap and a blazer. This is the ideal casual look of every mom at school drop-off like Princess Diana dropping Prince William and Prince Harry off to Wetherby’s School.
Her Signature Look
While watching a polo match with young Prince William, Princess Diana wore what could arguably be called her signature fall look. Boots, jeans, a t-shirt and a blazer.
Going Green For Fall
Princess Diana’s green v-neck sweater and blouse paired with a knee-length skirt worn in 1980 is an easy look for fall, also please note her green tights and loafers.
Sometimes A Girl Just Needs A Long Coat
When Princess Diana visited the island of Barra in 1985, she covered up in a calf-length rain coat with navy plaid liner. It looked rainy, smart.
Who Says You Can’t Wear White After Labor Day?
Princess Diana’s navy sweater and straight-leg white pants are a real look for fall, no matter what old fashioned style rules might tell you.
Sharper Than The Military
In October 1985, Princess Diana visited a military base in Germany. Her green and black tailored suit was the sharpest look around.
Red For Early Fall
Princess Diana brought Prince William to school wearing a red pencil skirt with navy blouse and red and navy flats. This is a fresh, clean fall look.
Getting Wet In Canada
Prince William and Prince Harry got to play a bit of hooky with their mom to visit Canada in October 1991, and they wore matching rain gear to tour Niagara Falls together.
That Black Sheep Sweater
Here is a sweater look Princess Diana rewore time and again. Her “Black Sheep” sweater from Warm & Wonderful. Iconic.
A Highland Fling
Princess Diana looked every bit the Scottish lass when she was visiting Balmoral with Prince Charles and their two little boys in 1988. Plaid skirt, white blouse, little tie... all amazing.
Getting Jaunty In Maroon
Not everyone can pull off a maroon velvet look complete with ruffled collar and jaunt hat plus a feather. But not everyone is Princess Diana.
Puzzles With The Prince
Prince William was enjoying some at home time with mom Princess Diana at Kensington Palace, and she was dressed for the part in a cozy red cardigan and white blouse.
The Most Mom Look Yet
Princess Diana’s head-to-toe running suit worn on a 1985 visit to Germany, complete with white sneakers, is the most mom outfit yet.
Going Full Equestrian
In a cream colored turtleneck and black double-breasted blazer, Princess Diana looked like the classiest equestrian on the block.
Which is very on brand for her.
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