The significance of Jackie Kennedy’s groundbreaking second wedding dress

Think of Jackie Kennedy and there might be two images which come to mind. One, being a prim first lady in the early 1960s with a wardrobe full of neat Chanel-esque skirt suits and pillbox hats. The second might be the same woman in her “Jackie O” era – all oversized sunglasses, effortless New York street style and liberated party dresses.

Jacqueline Kennedy Onassis’s extraordinary life is reflected in her clothes. There was always a “Jackie” thread running through her every style choice – from those she made as an East Coast socialite-in-training, to her time as wife of US president John F Kennedy, through to her later years as wife of shipping magnate Aristotle Onassis and then as a book editor and political campaigner. However, the style icon still had some very distinct fashion chapters.

And if one item encapsulates her move from former first lady to glossy international star, it has to be the Valentino couture wedding gown she wore for her wedding to Onassis in October 1968. For the ceremony, which took place on the Greek Island of Skorpios, Jackie commissioned an above-the-knee dress that couldn’t have been more different to the grand gown she donned for her first wedding to JFK in 1953.

“Jackie’s [second] wedding dress was groundbreaking at the time,” confirms Marissa Speer, US head of sale for luxury handbags and fashion at auction house Bonhams, where the dress will be auctioned for the first time in a sale taking place online from 16-26 September.

“Being a prominent public figure with a distinctive style, she chose to wear something unexpected for her wedding – a short dress. The wedding dress really highlights that she was embracing not only Sixties fashion and the feminine movement of the time, but clearly indicates that she was moving into a new era, making her own choices and showing her independence through her style,” Speer continues.

Jackie’s decision to ask Valentino to create her dress, which is being sold by a couple who worked on Onassis’s yacht, Christina, is also telling. As first lady, she had been under pressure to wear American designers. She would often get around this by commissioning her personal couturier Oleg Cassini to make Paris-quality pieces for her on US soil. This, or she would buy from boutiques such as Chez Ninon on Park Avenue in New York, which was licensed to reproduce European designs in American workrooms.

No such diplomacy was required for life as the wife of one of the world’s richest men, and so she could turn to Valentino, who was one of the most sought-after designers of the period.

“In the sixties, Valentino was the designer of choice, he was highly sought after and had a large following in Italy and the Mediterranean,” Speer explains. “He was the first designer to create a themed collection with his all-white “Sfilata Bianca” collection, making him in demand with brides of the day. At the time, Valentino was the equivalent of having McQueen or Westwood design your wedding dress in the 21st century.”

And while the dress might appear remarkably relaxed, Speer explains that the craftsmanship was as meticulous as you’d expect from Valentino. “From an archivist, collectors’ point of view, the dress ticks all the boxes in terms of an item of sixties Valentino. It was created in exquisite materials of silk crepe with intricate lace details that Valentino was known for,” she says.

“The cut, especially the bishop sleeves, are incredibly flattering and ultimately the condition is second to none. With a lot of Sixties fashion, you tend to see deterioration of the threads and fabrics, but the wedding dress is in exceptional condition, there isn’t a rip or tear. Valentino’s use of quality fabrics and craftsmanship have stood the test of time.”

Looking back at images of Jackie from the era, the dress represents a definitive bookmark between the Kennedy (or “Queen of Camelot”) years, as Bonhams describes it, and the Jackie O chapter; a moment of sartorial liberation, between her prim, safe first lady wardrobe and the relaxed ease of a woman who could spend her time holidaying on Greek yachts and socialising in New York.

The dress is also testament to her impeccable personal style, a trait which she passed on to her son, John F Kennedy Jr. Bonhams’ auction also includes three outfits (two Calvin Klein suits and a Giorgio Armani coat) which were worn by JFK Jr. in the early Nineties, when he was considered one of the world’s most eligible and handsome bachelors. They are being sold by his close friend Sasha Chermayeff, who also auctioned a Yohji Yamamoto dress owned by his wife Carolyn Bessette-Kennedy earlier this year at Bonhams.

JFK Jr. “had a natural ability and understanding of how to style clothing in an effortless and cool way – quite an achievement considering much of his wardrobe was suiting,” observes Speer. “One of the lots is a tailored nineties Calvin Klein suit. When you look back at menswear of this era, it’s all very flouncy and loose, so the fact JFK Jr. owned such a tailored piece at the time was trailblazing. It is so modern and could have been taken from a recent Tom Ford runway.”

The suits not only represent what Jackie had taught her son about dressing well, but the Calvin Klein designs nod to John’s meeting with his wife, who was working as a publicist and VIP coordinator at the label when he visited the atelier, making the couple and their relationship intrinsically linked to the sleek, minimalist look of the moment.

Whether it’s Jackie’s polished glamour or JFK Jr. and CBK’s cool sophistication, the allure of Kennedy style remains potent today (all three died in the nineties – Jackie from cancer in 1994 and John and Carolyn in a plane crash in 1999).

“With the trend of “Quiet Luxury”, the demand for timeless elegance is back, and this way of chic dressing is how the Kennedys dressed,” reflects Speer. “They opted for  classic designs with tailored silhouettes, crafted in beautiful fabrics rather than trend  or fast fashion pieces. So many of their outfits are timeless – in photos you can’t tell the time they are from, apart from the world around them.”

Bonhams Classic Luxury: Style Icons Online sale will run from 16-26 September at Bonhams.com