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Princess Diana's most iconic winter outfits

We're taking notes...

princess diana best winter outfits
Carla Challis
Commerce Partnerships Editor
Updated: 19 December 2022
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Find yourself constantly reaching for the same trusty denim jeans and jumper combo for your winter fashion look? With the weather getting colder and the practical part of our brains telling us to dress for warmth not fashion, it's a tricky time of year to look and feel your best. There's nothing wrong with throwing on a cosy knit, but Princess Diana never seemed to suffer from a limited winter wardrobe.

Hello! Fashion shares Princess Diana's best winter outfits to inspire your style game this season: 

Cream co-ord 

Princess Diana Wears Cream Jumper And Pleated Skirt© Photo: Getty Images

A knitted sweater and a pleated skirt in matching or coordinating colours like Diana's is a foolproof way to smarten up your winter style repertoire.


Princess Diana Wears A Tartan Dress© Photo: Getty Images

Checks aren't only used for Scottish kilts - from skirts to blazers, the pattern is a regular fashion go-to for the colder months. We're loving the warm autumnal hues in Diana's dress by Caroline Charles that she wore to the Braemar Highland Games, but if you fancy a more low-key tartan addition, we recommend a subtle scarf. 

Statement socks 

Princess Diana Wears Polka dot Socks© Photo: Getty Images

If you're not a fan of tights, don't forget the humble sock. We love how Princess Diana matched hers to her polka-dot skirt, but glittery or sheer ones work just as well. Team with loafers or kitten heels for maximum impact. 

Iconic jumper 

Princess Diana Wears A Sheep Jumper© Photo: Getty Images

Princess Diana rocked her famous red and white sheep jumper to the polo in the 1980s and American label Rowing Blazers has revived the archive design with the blessing of the original brand Warm & Wonderful. 

warm and wonderful sheep jumper

Sheep sweater, £310, Rowing Blazers


Plush velvet 


Princess Diana Wears A Black Velvet Dress© Photo: Getty Images


The royal looked picture perfect attending a performance of Les Misérables at London's Barbican in a Bruce Oldfield velvet gown. Because of its lustrous finish, the fabric is frequently used to exude glamour - and Princess Diana's chic black maxi dress is a case in point.

The cool-girl cardigan


Princess Diana Styles A Cardigan With A Wicker Bag© Photo: Getty Images


Cardigans get a bad rap, but we can't understand why. Style a lightweight version over a silky cami for a cooler alternative to a jumper, or brave the cold and opt for a more daring version by Jacquemus or Reformation. 

Double denim 

Princess Diana Wears Double Denim© Photo: Getty Images

Denim on denim is not for the fainthearted, and yet Princess Diana pulled off the current fashion trend with ease. Take your cues from the royal and break up your denim pieces with a textured leather belt and a glossy jacket. 

Cap it off 


Princess Diana Wears A Navy Cap© Photo: Getty Images


Swap your knitted beanie for a cap this winter. They look street smart with a heavy material blazer over a sweatshirt but also great for weekends with a puffer jacket and trainers.

Layering masterclass


Princess Diana Layers Pink Sweater Over Cream Polo Neck© Photo: Getty Images


Salmon pink and layered over a cream turtleneck – Princess Diana is hitting two trends in one with this layering trick. A pastel-hued sweater styled with a neutral base layer works perfectly with high-waisted jeans.

The French-girl hair moment 

Princess Diana Wears A French Side Comb© Photo: Getty Images

Sometimes the best hair trends are the ones that require practically zero effort. Follow Princess Diana's lead and rock a retro-feel French side comb this season.

Textured trend

Princess Diana Wears Red Fluffy Coat© Photo: Getty Images

The royal style icon wasn't one to shy away from a statement coat and this fluffy red version is spot on for this season. If you fancy giving your outerwear game a textural overhaul, keep an eye out for cosy teddy fleeces, luscious faux furs and shaggy Afghan styles. 

Trouser take-over 


Princess Diana Wears White Pinstripe Trousers© Photo: Getty Images


Looking for something smarter than denim? Tap into the straight-leg trouser trend, and bag a pair that can be worn for either work, rest or play. Princess Diana styled hers like a pro with a navy knit and classic Chanel pumps, but we reckon straight-leg trousers would look killer with a glittery corset this party season.

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