Princess Dianas Best Looks

10 Of Princess Diana’s All Time Best Looks

September 9, 2022Heather

I can’t image why, but over the past couple days I’ve been thinking about Princess Diana (and who in power was responsible for death, ah-hem). And what do we think about when we think about Princess Diana? Her looks, obviously. Name a more beloved sytle icon. You can’t! What JLo thought she was doing with that Versace dress, Diana Spencer undeniably did with the Revenge Dress. So, for no particular reason, in no particular order, here are, ten of Princess Diana’s all time best looks.

Princess Diana style
Image via W Magazine

First up, we have a look I lovingly call “Monochromatic Queen”. Lavender? Indeed! I’m not just saying this because purple is my favorite color and Diana Spencer if my favorite royal, but this look is top tier. We’re mixing prints, we’re adding feathers, we’re working accessories, it’s everything I want from our Queen.

Princess Diana fashion
Image via Who What Wear

No one did casual like Princess Diana! I’m itching to grab my iron and get to work just looking at the creases in those straight leg jeans. And that sweatshirt and hat combo? Practically screaming Hailey Bieber. A two-toned flat? Give it to me now. Also I love William’s penny loafers but instead of pennies he probably has rare African medallions that his ancestors stole in them.

Princess Diana revenger dress
Image via InStyle

Perhaps the most famous dress of all time, on the most famous woman of all time. WHAT A MOMENT! A cultural reset, a f*ck you to Charles and the Royal Family, and a signal to the world that Princess Diana wasn’t going to sit at home and mope. I love revenge! I love the Revenge Dress!

Princess Diana ski
Image via Refinery29

Firstly, I think skiing is the pits. You freeze, you spend an insane amount of money, you ache, and for what? To go down a stupid hill? I’m debating taking up skiing just to recreate this outfit. I didn’t know I needed how badly I needed a thick braided headband.

Image via CR Fashion Book

This outfit has always held a special place in my heart. Maybe it’s the early 90s preppy Ralph Lauren vibes, maybe it’s the chambray shirt, a favorite closet staple of mine, or maybe it’s the fact that Charles is visibly injured and I want him to have nothing nice or good. Any way you slice it, I love this outfit.

Princess Diana plaid
Image via Glamour

I was recently shopping and felt myself being pulled toward a plaid blazer. The plaid was holiday-ish, and the blazer had touches of velvet and a hearty knitted feel to it. I couldn’t figure out why I was so drawn to it, and then I realized; it was a reincarnate of Diana’s plaid, velvet detailed coat dress that I think about at least once a week. In a cruel twist of fate the blazer did not fit me, but I live to shop another day.

Princess Diana overalls
Image via Royal Roster

Overalls?! That’s the People’s Princess for ya! I know her pale yellow overalls outfit (beautifully recreated in The Crown) is a fan fave, but as a lover of white overalls I wanted to share this image. Pairing a casual denim overall with striped button down is *chef’s kiss*…and I think I might need to recreate this look ASAP.

Princess Dianas best looks
Image via Daily Mail

Now this is glamour! The shine, the texture, the color! Additionally I should mention this dress was backless, making it especially daring for a member of the Royal Family. Diana wore this Bruce Oldfield dress to the James Bond A View To Kill premiere and she undeniably gave us a look to kill. If I ever need to do high glamor, this will be my inspiration. Also I could talk forever about how Pierce Brosnan was supposed to star in A View To Kill (a role he would eventually get years later) but NBC wouldn’t let him…

Princess Di looks
Image via Elle UK

A moment for this iconic boiler suit and pink Converse please? I’m rather obsessed with boiler suits (seriously, you need one, or five) and no one has ever looked better in one than Diana Spencer. I mean this could be a 2022 Street Style pic. This outfit is inspiring, I am particularly inspired and henceforth I will call my boiler suits “Diana suits”.

Princess Dianas best looks
Image via W Magazine

Did somebody say icon? Princess Diana’s gym looks are legendary! Am I going to recreate this look all weekend? Without a doubt.

No go forth and recreate and reinterpret your picks for Princess Diana’s best looks straightaway!

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