Princess Diana was able to communicate through clothes like no one else. Her style was always classic and impeccable. Her outfits were truly iconic.

We find fashion inspiration and styling ideas all around us in films, photography books, fashion magazines, and amongst billions of online images. I was up late one-night scrolling through images of Princess Diana and decided to challenge myself to recreate some of her outfits from clothes hanging in my closet.

While she always looked amazing, she was a quite conservative dresser. The biggest challenge for me was to find conservative basics in my wardrobe of statement clothing. Also, I needed to style these outfits in a modern way as I would actually wear them today therefore, there are some variances in these outfits that I put together inspired by Diana.

Diana’s Style Re-Imagined

I’ve styled a vintage Ralph Lauren navy blazer with vintage Levi 517 jeans, a Topshop blouse, and Converse sneakers.

This outfit was fun to recreate. I’ve styled a black vintage Pendleton blazer that I scored at Goodwill for a few dollars with a graphic tee that I bought in a shop in New Orleans, G-Star Raw jeans, cowboy boots, and my Dad’s ball cap.

I don’t have a plain cotton button-down or straight-leg mom jeans so this outfit is a bit dressier than her wonderfully casual look. I put this look together with a vintage beige silk blouse, Helmut Lang pleated trousers, and Michael Kors loafers.

Remember wearing dark opaque tights, all the time? They used to be part of my everyday wardrobe, now I wear them only occasionally.

I styled a pair of black Diane von Furstenberg pants with a black blouse and vintage cardigan. This cardigan is one of my favorite pieces. I adore the details such as the buttons and bows.

Princess Diana’s white pearl and sequin dress and bolero jacket designed by Catherine Walker are exquisite. I don’t own anything so formal but the detailing on this vintage trophy jacket is a fair interpretation. I bought it a few years ago from @busyladybaca and I’m wearing it with a black t-shirt and jeans and again with a beaded top from ASOS.

Diana: Her Fashion Story, Kensington Palace Exhibition

In 2018, I had the chance to see many of Princess Diana’s most memorable outfits at an exhibition of her clothes at Kensington Palace.

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More vintage styling tips on Mad Chipmunk

How To Build A Vintage Wardrobe