Princess Diana’s most iconic fashion moment is often considered to be the famous ‘revenge dress’.

On the very night that Prince Charles publicly admitted to infidelity, Diana made headlines in a daring off-the-shoulder black dress by Christina Stambolian – a look that would become legendary.

However, there was another little black dress in her wardrobe that predated this moment: one she wore at just 19 years old, during her first official engagement alongside her fiancé.

In May 1981, Lady Diana Spencer attended a charity recital at Goldsmiths’ Hall, wearing a strapless taffeta gown designed by David and Elizabeth Emanuel, who would later create her wedding gown.

Prior to the event, Diana visited their studio to request an outfit for a ‘posh’ evening function. After trying on a black silk taffeta bodice, which happened to be on display, it was clear the style complemented her blue eyes and blonde hair.  

Concerned that the strapless silhouette revealed too much skin, David crafted a matching black wrap for Diana to drape over her shoulders. 

Reflecting on the moment in an interview with Today, he recalled: ‘That evening, when we switched on the news, this limousine pulls out, out got Prince Charles and there was this girl, and I said, “That’s the girl! That’s her! That’s the one we’ve just done the frock for!”‘

Previously known for her preference for pastel hues and soft tulle fabrics, Diana made a striking shift towards a more sophisticated style – marking the early signs of her evolution into a global fashion icon. 

In May 1981, Lady Diana Spencer attended a charity recital at Goldsmiths’ Hall, wearing a strapless taffeta gown designed by David and Elizabeth Emanuel – who would later create her wedding gown

But Diana appeared uneasy and later described the event as a ‘horrendous occasion’.

In recordings for Andrew Morton’s biography Diana: Her True Story – In Her Own Words, she recalled her anxiety, saying: ‘I didn’t know whether to go out of the door first. I didn’t know whether your handbag should be in your left or right hand.

‘I was terrified, really – at the time everything was all over the place,’ she continued. ‘I remember that evening so well. I was terrified – nearly sick.’

Adding to her discomfort, Diana felt her dress was ‘two sizes too small’ and inappropriate for the event. 

The gown was low-cut and black – a colour Charles criticised her for, as it is traditionally associated with mourning.

According to Morton, Diana struggled with self-consciousness throughout the evening, which was noticed by Princess Grace of Monaco. 

At the gala, Diana appeared uneasy and later described the event as a ‘horrendous occasion’

Diana was 19 years old during her first official engagement alongside her fiancé Prince Charles

In recordings for Andrew Morton’s biography Diana: Her True Story – In Her Own Words, she recalled her anxiety, saying: ‘I didn’t know whether to go out of the door first. I didn’t know whether your handbag should be in your left or right hand’

Diana felt her dress was ‘two sizes too small’ and inappropriate for the event

The gown was also low-cut and black – a colour Charles criticised her for, as it is traditionally associated with mourning

According to Morton, Diana struggled with self-consciousness throughout the evening

Grace took Diana aside to the ladies’ room for a private conversation, during which Diana shared feelings of loneliness and anxiety about her future. 

Grace, in an attempt to comfort her, gently patted Diana’s cheeks and said: ‘Don’t worry, it’ll only get worse.’

This poignant moment between the two princesses took place around 18 months before Grace’s untimely death in a car accident.

Diana would later marry Charles, but the union turned out to be unhappy and ended in divorce shortly before Diana herself tragically died in a car crash.