This Is the Princess Diana Way to Style Boots for Winter

princess diana winter outfits

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I love remembering Princess Diana through a fashion lens because she so clearly enjoyed expressing herself through her clothes. She was a fearless dresser and loved experimenting with the trends of the moment, but she also appreciated classic pieces.

Her style evolved significantly over the course of her tragically cut-short life. When Princess Diana emerged in the spotlight after getting engaged at only 19 years old, she favored twee sweaters, youthful overalls, and Peter Pan collars. In her 30s, she wore a lot of sharp skirt sets and tailored coats. She also gained more and more confidence as she adjusted to her post-divorce life, which was absolutely reflected in her fashion sense. Revenge dress, anyone? In homage to the late, great Princess Diana, scroll down to re-create some of her best winter outfits worn with boots. 

1. With a Double-Breasted Red Coat
princess diana winter outfits

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On a snowy day in Sandringham in 1985, Princess Diana wore a beautiful double-breasted red coat with knee-high patent boots, and her outfit is still as chic as ever in 2023. 

2. With a Midi Skirt and Chunky Scarf
princess diana winter outfits

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Princess Diana accompanied the Duchess of York on a ski trip to Switzerland, where she bundled up in an oversize scarf and cozy sweater. 

3. With Corduroys and a Printed Sweater
princess diana winter outfits

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Shortly after announcing their engagement, Prince Charles and Diana Spencer posed for photos in Scotland. Her cute printed sweater and classic Hunter boots would look right at home in 2023. 

4. With Sweatpants and a Blazer
princess diana winter outfits

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Princess Diana went casual in sweatpants and a baseball hat but polished up her look with a roomy blazer. Chic. 

5. With a Tan Coat
princess diana winter outfits

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Princess Diana's style remains a huge inspiration to fashion fans in the present day, and this polished, classic outfit is certainly no exception.