Princess Diana: Modern Style Icon

Princess Diana Modern Style IconPrincess Diana Modern Style Icon

I had idolized Princess Diana while I was growing up. I was one year old in 1981 when she stepped out of a gilded gold carriage and on to the world stage, and for the next 16 years, she was the most photographed woman on the planet. She was everywhere, in the very ethos of my childhood. While my friends were dog-earring pages in Delia’s catalogs, I was an awkward 13-year-old, reading Vogue and Andrew Morton’s “Diana: Her True Story” dozens of times.

Diana had been the epitome of the 80s style, wearing full skirts, puffy sleeves and over-the-top embellishments, and she ruled the 90s, as well. With a greater sense of self-confidence and a newly found independence, she came into her own being, and I was enthralled. So much is made of her style choices and for a good reason. Her fashion told a story, created moments, and remained a relevant piece of history for the last 20 years since her death.

There’s no denying her status as a style icon, but what made her special was how she wore her clothes and the thought that she put into each outfit. It’s well documented how she carefully considered every outfit, making sure it was appropriate for each event. If she was visiting a homeless shelter or hospice, she wanted to be able to move and hug those she was visiting. If she were visiting a foreign country, she would opt for one of their local designers, understanding the message behind the gesture. Similarly, she supported London-based designers when doing local work, establishing a lovely tradition. Michelle Obama did a beautiful job carrying on that philosophy, advocating for American fashion while also honoring international design houses during her time as the first lady.

Diana was loved throughout the world because she genuinely showed up. She was complicated, kind, flawed, funny, devoted to her boys, and a champion for those who didn’t have a voice. Her vulnerability allowed millions of people to feel connected to her. She didn’t seem to care about being perfect; she was a rebel within the institution of the royal family and did what she wanted because she knew it was the right thing to do, regardless of whether it was popular. Her work with AIDS, leprosy, and landmines were all controversial topics at the time, and her support of them changed the world for the better.

A common thread found throughout Diana’s public work and personal style, and I imagine that in her private world, she was still a lady. She was irreverent at times (in the best possible way), but she always carried herself with grace and dignity, no matter what was going on around her. I learned how to walk into a room by watching her navigate crowds. As a tall, awkward teenager, I was so uncomfortable in my skin. I couldn’t figure out what to do with my limbs; I was so insecure about my height and being so skinny (not anymore!) and, in general, just always felt like a weirdo. In Diana, I saw what I wanted to grow up to be: confident, sophisticated, and charming – not that I think I’m any of those things – but, you know what I mean. She walked tall, always open, with her arms extended, and gave everyone her full attention. To this day, I model her in every interaction, especially in my corporate work where I’m always meeting new people.

When we were in London last month, the only thing I wanted to do was visit the Diana: Her Fashion Story exhibit in Kensington Palace. It was incredible. What struck me most as I walked around some of her most legendary outfits was how easy it would be to wear them today. I always knew she was a huge influence on my personal style, but even my husband took note, and I could repaint our entire house, and he would never notice.

Today, we’re breaking down some of her classic looks, highlighting the elements that make them so timeless, and, of course, showing you how to take the inspiration into real life.

Princess Diana Modern Style Icon Chic Casual Basics

Jeans, $168; Shirt, $158; Blazer, $96; Flat, $134; Bag, $40; Earring, $65

Diana’s casual chic look in the ’90s requires little adjustment to make it work today.  All you need to do is give the jean a slimmer leg and narrow the shoulders of the blazer.   To create this look  I used my favorite travel jeans by DL1961, a classic chambray button down, and a schoolboy style blazer from J.Crew .  Pair them together and you have an easy, modern everyday outfit. Finish the look with this simple tote for $40 and I added these vintage Chanel earrings as a node to the throwback inspiration.

Princess Diana Modern Style Icon Sophisticated SheathsDress, $248; Pump, $84; Bag, $165; Earring, $26; Bracelet, $245

No one wore a dress better than Princess Di. In my professional wardrobe, I turn to a sheath time and time again.  I love the balance of feminine with structure and find they work in just about any environment. Elements of Diana’s look translate seamlessly today: a modest neckline, knee length skirt, and impeccable tailoring. What I love most are her neutral-to-her skin tone pump and coordinating bag.  This look was easy to put together.  A classic red sheath can take you from the office to an after work event. Pair it with a neutral pump, which extends the length of your leg.  This bag is so gorgeous.  I wouldn’t take it to the office, but I would carry it as a clutch alternative for a business dinner.  These earrings mimic the hardware of the bag creating balance.  For fun, I added a sparkly link bracelet, not as much as a specific recommendation but as inspiration to pull out your better pieces and incorporate them into your everyday looks.


Princess Diana Modern Style Icon Classic Cocktail

Dress, $385; Earring, $45; Bag, $145; Shoe, $325

When you’re husband goes on television and tells the world that he’s cheated on you with his old girlfriend, you have two choice: retreat into a corner and feel sorry for yourself, or put on a killer dress and hit the town.  In 1994 Diana stepped out in what would be dubbed “The Revenge Dress,” changing the narrative and headline from” Diana the Victim”, to “How Stupid Can He Be?”

Keeping a cocktail look classic doesn’t mean you have to sacrifice looking sexy, it’s a matter of balance.  In this case the neckline is stunning, flattering and shows just enough –  I am obsessed with it – but the length prevents it from looking over done.  How amazing is it that a dress she wore 20 years ago could go to your next cocktail party?  I found the modern version of the dress by Cinq à Sept.  Depending on your height you will want to shorten to your best length.  Even with my height, I would take it up a bit. Just remember the longer the length the higher your heel.  To mimic the look you could wear something like these L.K. Bennett classic pump.  They’re just a solid shoe you’ll wear to death.  For a more modern and affordable shoe option you could wear a strappy high heel sandal.  I’m not even going to try to find something similar to her pearl and sapphire cocker, instead, an elegant and affordable drop earring works beautifully.  Finally, this modern clutch from Rebecca Minkoff can go anywhere from a bar or a black tie wedding.

Did you have a favorite Princess Diana look?  Share your thoughts in the comments.  

Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.


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