Style Lessons Princess Diana Taught Us

Forever style icon <3.

I’m not really a crier when it comes to movies. Unless the film in question catches me at exactly the right moment in my cycle (take right now for instance, where I’m tearing up two sentences into Beyoncé’s historical Vogue cover story), Kleenex are a non-requirement for watching. 

Princess Diana’s Netflix documentary Diana: In Her Own Words is a damp exception to this rule. I ugly-cried my way through a big chunk of it, finally truly understanding why so many tears were spilled in my household following her death in 1997 (I was 6-years-old and slightly confused as to why my Mum and Nan held each other crying in front of the TV for what felt like years over someone we didn’t share a last name with). The ultimate empath, Princess Diana recognised her privilege and her celebrity, and used that giant platform for the betterment of stigmatised and disadvantaged people all over the world. 

And today, Diana is remembered as much for her bold yet elegant style as she is for her compassion, wit and progressive worldview. As all good fashion icons do, her outfits were reflective of society at the time, managed to push boundaries, speak to her evolution as a person, and stand up to the ol’ test of time. Her outfit choices feel more 2018 than any of the royal outfits do today (soz, Kate), which is why she’ll always be our #1 style queen. 

Princess Diana’s style will always excite and inspire me. Here’s 10 key lessons her bold-yet-effortless personal style has taught me over the years… 

It’s Okay To Reinvent Yourself

I used to be wary of changing up my look too drastically, breakups and holiday wardrobes notwithstanding. People will think I’m nothing but a mindless trend-sheep, I thought, as though my humble style was so important as to constitute a talking point between two outside parties (it’s not). That’s one of the fun things about getting older—there’s freedom in not caring what people think, including but not limited to: reinventing yourself whenever you damn please.

Princess Diana’s style was a true testament to this. The evolution of her style was more than just an aesthetic shift—it reflected her personal growth from a shy, quiet teenager to a strong, empowered woman that was comfortable in her own skin.  

But It’s Also Okay To Stick To What You Know 

‘Effortless’ is used in reference to Princess Diana’s style all the time, but in no way should that be conflated with ‘safe’. Diana took risks, but they never seemed contrived; more a genuine extension of her personality. And, her signature style comprised of all the things you’d likely find in our wardrobes today—you guessed it: blazers, jeans and white t-shirts.

Shop the look: Grab yourself the perfect pair of vintage Levi jeans, add a good quality white t-shirt to your cart, followed by a check blazer, tortoise-shell sunglasses, and a medium-sized bag with bamboo handles, and never experience a style rut again in your life.

Polka Dots Are As Timeless As Your Fave White Tee

Sure, polka dots were ubiquitous in the 80s, but unlike my mum’s dated take on the trend (sorry, love you), Princess Diana had a knack for ensuring they stood the test of time. I can also single-handedly thank the heavenly human for re-contextualising polkadots in my mind from a cheap, fast-fashion fad to something that should sit in the same basket as white t-shirts, jeans and margarita pizza when it comes to timelessness. Mmm, pizza.

Shop the look: This Rixo London top is a perfect desk-to-dranks option, but this Lisa Marie Fernandez will have you feeling like a true polka dot princess in no time (although, if you don’t want to fork out for the royal treatment, this one-shouldered Valencia & Vine dress is simply s-t-u-n-n-i-n-g).

Sleeves Were Made To Be Puffed 

Again. Whereas most 80s iterations of the trend would look garish and dated thirty years on, Di had a genius ability to make trends era-defying. Excuse me while I print this image off and stick it to my wall, to refer to whenever I feel a style rut is afoot.

Shop the look: I guess this begs the question—do you want to lean into the prairie aesthetic, or are you happy to illicit images of 80s aerobics clips with your sartorial choices? There are no wrong answers here, friends! For the former, I’d recommend this Reformation blouse, and for the latter, this Rejina Pyo number should tastefully do the trick.

Tights Shouldn’t Be Worn Outside The Gym, EXCEPT If They’re Bike Shorts 

Look, as time goes on my firm ‘tights are not pants’ mantra is waning—I’d probably live in Outdoor Voices leggings if I could. No matter—bike shorts have always been, and will always be a perfectly acceptable choice when it comes to shorts for any occasion in my mind, and I owe it all to Princess Diana and this iconic image of her in them.

Shop the look: Take the casj bike shorts lewk to a cute place with a Comme des Garçons hoodie, a very affordable pair of Pretty Little Things bike shorts and these Stella McCartney sneakers.

Dressing Like A Daggy Dad Is Cool 

Flawlessly-timed dad jokes aren’t the only thing I want to inherit from my old man—I also want to steal his lewk. Diana did daggy dad better than any daggy dad ever has, though, so let’s look to her for inspo.

Shop the look: If Princess Diana (and my dad, credit where it’s due) have taught me anything, it’s that comfort and style are not mutually exclusive. With that nifty little tip in mind, I’d like to introduce you to these ultra-comfy Bassike jeans, this Tommy Hilfiger sweater, this oversized black blazer. I’ll tip my cap to that!

You Don’t Need A Yacht To Dress Like You’re Part Of A Yacht Club

Ladies and gentleman, I have officially found my summer 2018 lewk. While I’m more likely to be drinking a gin & tonic in a kayak than I am sailing around on a yacht, good luck telling my summa wardrobe that. Dress for the leisurely activities you’d like to dabble in, I always say!

Shop the look: Loafers, capri pants, white linen shirts, and oval shades are all non-negotiables.

An All-White Lewk Is Always Elegant 

An all-white outfit is crisp, elegant and will have you feeling like Natasha Richardson’s character in the Parent Trap in no time (a.k.a another beautiful, stylish kween). Teamed with (bottle-aided) sun-kissed skin, a simple square-neck white dress, drop earrings and strappy 90s heels, it is the ultimate girl-on-holiday vibe.

Shop the look: Did someone say holiday? My shopping cart appears to have heard you, hence why it’s filled with this Organic by John Patrick white slip, these drop pearl earrings, and these Rupert Sanderson mules that are so perfect I just had to pinch myself, to make sure I didn’t dream them up.

But, Honestly, Nothing Beats All-Yellow 

Yellow paired with gold is the epitome of cool, effortless steeze, and judging by Diana’s smile, don’t she know it. Pastel yellow and linen were made for each other, so keep both eyes peeled for that combo this summer (or, you know, take a look below). Loose-fitting shirts and easy, breezy trousers are a match made in heaven, especially when they’ve got a pair of gold shoes in tow. 

Shop the look: This Lisa Marie Fernandez one-shouldered dress is about to go into battle with my bank account, because I HAVE TO HAVE IT, OR ELSE. These Marni pants know what’s up, and it seems they’ve let this Jil Sander shirt in on the secret. But the feet, I hear you cry! To which I say, Have you met these Tony Bianco gold loafers?

Woo! Glad I could facilitate that cute meet!

Dress Codes Are Meant To Be ~Interpreted~

Princess Di was not your typical princess—both in her unwavering commitment to humanitarian pursuits and in her refusal to conform to the b-o-r-i-n-g dress codes expected of her. In 1981 she made her first official appearance wearing a strapless black dress that *shock horror* showed off her décolletage, and while she admits to have felt uncomfortable in her ~daring~ choice (likely because of the way she was treated by stuffy rule-abiders), it set the tone for her being a princess of the people who took style risks that’d feel right at home today. <3. 

Words, Madeleine Woon