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Image / Fashion

Taking a moment to remember Princess Diana’s key style moments


by Marie Kelly
22nd Feb 2020

Princess Diana would have turned 59 this year. She was born in 1961 and entered the public arena in 1981 when she and Charles got engaged. She led a remarkable life until her death in August 1997. At IMAGE HQ,  we often mention her style highlights. Marie Kelly takes more than a moment to capture them for us all.


Like many of us, the most poignant fashion memory I have of Princess Diana is the appearance she made in the black dress by Greek designer Christina Stambolian at the Serpentine Gallery’s 1994 summer party. Before this, a little black dress had always been considered the safe, reliable and unthreatening option, but Diana reinvented it as the ultimate showstopper. The LBD was now the weapon with which you struck a blow to the man who broke your heart and the mistress who stole your dignity.

She may not have won back her prince that evening, but she gained the admiration of every woman and the awe of every man who saw her. Diana had a way with clothes. She made cleavage look chic rather than cheap, shift dresses seem sexy not safe and a simple white shirt the height of good taste. But it wasn’t just her long, lithe limbs that gave her an advantage. Her characterful face, with its strong prominent nose, imbued her with an air of authority and, more importantly, personality. She never just looked like a clothes horse.

Diana was fearless when it came to fashion. She made choices that were deemed radical for a royal – asymmetric necklines, electrifying colours and statement jewellery – choices that would overwhelm Kate Middleton, who seems to have neither the confidence or fashion instinct to develop a personal style that pushes the royal fashion narrative forward. I have high hopes for Meghan Markle however.

So many of Diana’s outfits would still look utterly modern today. This stunning Versace cobalt blue gown wouldn’t have looked out of place on this year’s Oscars red carpet. A big fan of the “cold shoulder” trend, which has been a dominant look for the past several seasons, Diana fully embraced her sexuality with body-skimming gowns, discreet flashes of flesh and smoky eye make-up that vamped up her big doe eyes, creating an intriguing juxtaposition between the smouldering fashion icon and the demure former princess (she was separated from Charles at this stage). Diana loved to confuse people’s expectations of her and she was an expert at using her own personal style to do it.

It’s so easy to pick out Diana’s red carpet successes, but for me some of her best, and most intriguing looks are when she’s in “private” mode. This I’m A Luxury jumper she wore as a young mother says so much about where she was in her life at this time. It wasn’t long after Harry was born that her relationship with Charles began to deteriorate. He may even have been seeing Camilla again at this point. Diana was sending out a strong message to her husband with this sweater, and more than likely, trying to persuade herself of the sentiment’s truth – we know Diana was constantly besieged by self doubt. Diana was continually silenced by royal protocol, so she learned very early on how to make her feelings known through her clothes.

In complete contrast, the image below shows Diana at her most confident. There’s something hugely iconic about this image because it portrays not Diana, Her Royal Highness, but the new, post-Charles Diana – goodwill ambassador, charity worker and philanthropist. Her choice of outfit is interesting because it’s so ordinary. Blue jeans and a white shirt could easily look generic and boring, but Diana made it her new signature, accessorising it with gold earrings and shades. By simplifying her clothes, she made the strongest statement of all, that she was happy and free to be the woman she wanted to be rather than the princess everyone expected she should be.


Read more: Baby Archie and his christening

Read more: Priyanka Chopra is right to call out the racist treatment of Meghan Markle

Read more: 10 of Kate Middleton’s best looks from Wimbledon

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