Jacqueline Kennedy’s Life: Tales, Fashion, Controversies, And Confidentialities Of The Adored First Lady

By: Lauren Wurth | Published: Sep 24, 2023

Considered to be one of the most stylish people of her era, Jackie Kennedy has worn hearts and turned heads wherever she went. Her charm was irresistible. Despite her lavish lifestyle, the former first lady was adored by the public who perceived her as a dazzling role model for all the women of the world.

Jacqueline Kennedy was many things. She was a good mother to her children, a responsible wife to John F. Kennedy, and, of course, a sensational icon for women of her era. Naturally, she had her fair share of scandalous stories, as most public figures do. Keep reading to learn more about the scandalous twists and turns and stories that went on behind the scenes in Jackie Kennedy’s life.

Who Was Jackie Kennedy?

Who was Jacqueline Kennedy? She was most comomonly associated with the former U.S. president, John. F Kennedy (JFK), as being his wife, but not many knew who she was outside of her marriage to JFK.


Source: Jackie Oswald/ Pinterest

Born in New York in 1929, Jacqueline’s mother was a socialite and her father was a stockbroker. With an emphasis on French Literature, Jacqueline graduated from George Washington University. It was during her studies that she, too, became a socialite and, not too long after, received the prestigious position of Vogue‘s junior editor.


The Beginning Of Jackie And John

Jackie had planned to get married to a stockbroker, John G.W. Husted Jr. in 1952, and everything was supposed to be wonderful. But, Jackie called it off, because Huston was boring and immature — the exact opposite of herself. Jackie decided to follow her heart, which proved to be the best decision she had ever made. Not too long after Jackie met John F. Kennedy during that same year, they were to become engaged.


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The couple had their wedding ceremony at St. Mary’s Church in Rhode Island in 1953. They had their honeymoon in Acapulco before settling down in Virginia’s Hickory Hill. Sadly, married life didn’t start too cheerily for the newlyweds. They experienced a miscarriage and a stillbirth, which was heartbreaking. However, in 1957, their luck changed when Caroline, their eldest child, was brought into the world.

Jackie Never Left JFK's Side

Jackie had her own responsibilities as the first lady, which came in addition to being JFK’s number one supporter and companion. More than any of her predecessors, Jackie made official international visits. When her son, Patrick, was born, she had to take a back seat to her duties, but he tragically passed away after his premature birth due to a hyaline membrane disease.


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In 1958, with Jackie’s incredible support, JFK secured re-election in the Senate. He made it known to reporters that her presence was more than crucial during his campaign. She also proved an invaluable asset in her husband’s bid for the presidency. Jackie gave birth to their son, John F. Kennedy Jr. just two weeks after JFK was elected president.

All About Jackie’s Girl AKA Kathy McKeon

For 13 years, stylist Kathy McKeon was Jackie’s live-in aide. McKeon released Jackie’s Girl, her autobiography that shed light on many revelations about the first lady. Most of these secrets, however, were all about Jackie’s wardrobe and style choices.


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In great detail, McKeon delved into the various styles that Jackie preferred and the secrets surrounding her shoes. Shoes? Why were her shoes so important? Well, McKeon divulged that Jackie’s shoes said a lot about her as a person.

Jackie's Wardrobe Was Mesmerizing

As being Jackie’s live-in aide, McKeon understood that she would be told many secrets. Not to mention, she had exclusive access to Jackie’s walk-in closet, which was fully stacked top to bottom of the first lady’s daily clothing choices. McKeon wrote in Jackie’s Girl that her shoes were “all arranged according to color. I had never seen such a dazzling selection of shoes!”

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It seems as though McKeon was enthralled by Jackie’s wonderful wardrobe. Taking a closer look, though, McKeon noticed a peculiar detail about her shoes, which needed to be oddly customized per Jackie’s request.


Who Was The Brains Behind Many Of Her Iconic Looks?

Unlike McKeon, Jackie’s long-time friend and fashion designer, Oleg Cassini, wasn’t surprised about Jackie’s shoe secret. Born into a Russian family of maternal Italian descent, Cassini had a passion for fashion and went to the United States to work for Paramount Pictures when he was an impressionable young man.

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Cassini made friends with many icons and began creating custom clothes for them, and his experiences as a designer certainly helped him. Jackie Kennedy was one of these famous icons with whom Cassini was tasked with creating her most notable outfits, as well as her interesting shoes.


Dressing Like Jackie Kennedy Comes With A Hefty Price Tag

As the first lady, Jackie Kennedy was expected to participate in living an extravagant lifestyle. From fashionable and recognizable dresses to accessories that made her stand out, Jackie was dressed to impress. She spent more than $145,000 on outfits and accessories in 1961. Talk about paying a pretty penny for your appearance!

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Jackie was voted the most stylish woman in the world, with big thanks to her iconic wardrobe and dazzling confidence. At the time, the price was all worth it because her wardrobe was largely admired and loved by the public.


The First Lady’s Choices

It is well-known that the first lady loved French labels such as Balenciaga, Givenchy, and Chanel. However, since she was the first lady of the United States, it was also expected of her to be patriotic. So, her love of French couture did not go down well with the American media.

Image: Corbis via Getty Images

Because of this issue, Jackie asked fashion editor Diana Vreeland to help her find American designers capable of creating clothes with a touch of Parisian style. As the editor-in-chief of Vogue, Diana Vreeland had a huge influence on the fashion world at the time.


The Chosen Ones

There were many designers to consider, but Vreeland chose Norman Norell and Ben Zuckerman to create clothes for the first lady. Norell was widely known as the “first designer of America,” while Zuckerman was chosen because of his notable take on Parisian couture.

Image: John F. Kennedy Presidential Library and Museum

In this photo, Jackie was talking to the former first lady, Mamie Eisenhower, the wife of the former president of the United States, Dwight D. Eisenhower. Jackie wore a woolen coat designed by Zuckerman for her famous White House tour.


Signature Look

Jackie’s signature look during her time at the White House was all about sleeveless A-line dresses, suits, low-heel pumps, and above-the-elbow gloves. Then, of course, there were her famous hats.

Image: Hulton Archive/Getty Images

Her go-to hairdo – the bouffant – was created by her hairdresser, Mr. Kenneth. As one of the most stylish women of her time, Jackie’s look was endlessly recreated by clothing companies across the country and the world.


More of Her Signature Looks

Though she changed her wardrobe, Jackie still shone with the same level of elegance and class. We knew a little about her influence on fashion and how she confidently strode into important events; however, we had no clue that she was, all that time, keeping the secret about her shoes hidden.

Image: Express Newspapers/Getty Images

Jackie Kennedy did not just have the classy signature look we mentioned beforehand. After her husband’s death, it seems that she changed her entire image. From sleeveless dresses and gloves, she switched to lapel jackets, silk headscarves, gypsy skirts, pantsuits, and round sunglasses.


Jackie’s Jewelry Collection

These two iconic jewelry designers gained a great amount of prestige because of their wonderful creations for the first lady. Aside from the necklace, and bracelet, Jackie’s most prized possession was her Van Cleef & Arpels wedding ring. Just like any happily married woman, Jackie considered her wedding ring to be her most cherished item of jewelry.

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Aside from her dazzling and stylish wardrobe, Jackie also acquired an elegant collection of jewelry. The first item she had as the first lady was a necklace by Kenneth Jay Lane. Aside from that, she was also known for wearing beautiful bracelets designed by Frenchman Jean Schlumberger.


A Knack for Organization

To be quite honest, McKeon was astonished at how well organized Jackie’s closet was. Aside from the fact that it was every woman’s dream to have a dazzling and organized closet, McKeon also said in an interview that, “It was extremely easy to find anything in it.” It just shows that even though the former first lady had a busy schedule, her closet was a safe haven of perfect organization.

Image: Kennedy Library Archives/Newsmakers

Heading back to McKeon’s autobiography, since the aide was in charge of Jackie’s closet, she saw how the first lady wanted it to be and how it should be organized.


Everything Matched!

As you can see in the photo, Jacqueline Kennedy had clothes for every occasion, and with her highly organized closet, she was prepared for any event. It just shows the variety of her clothes and how she was able to confidently rock any outfit.

Image: Art Zelin/Getty Images

Speaking to Fox News, McKeon explained that with Jackie, “A pair of pants would always be accompanied with the right blouse… and her shoes were always lined up. Nice and shiny.” Everything in Jackie’s wardrobe had its place, and this helped Jackie ensure every element of every outfit always matched.


A Closet Perfectionist

The former first lady went into all details in helping to renovate the White House. She took the same approach when reviewing the script for the televised renovation tour in 1962. This lady was indeed meticulous in everything she did.

Image: Underwood Archives/Getty Images

Jackie’s incredibly organized closet was just one example of many perfectionist tendencies. The former first lady was known to be meticulous, with an eye for detail and a desire for everything around her to be in order.


How Jackie’s Shoe Secret Came to Light

Some of these notes were sent to Bergdorf Goodman’s personal shopper Marita O’Connor. In them, Jackie included her instructions, catalog pages, sketches, and pieces of fabric to let them know what kind of quality and items she was looking for. Moreover, the notes included the exact dimensions that are requirements for her shoes.

Image: Bettmann/Getty Images

Jackie Kennedy walked around for decades with a secret no one knew about. However, her secret was out in the open where anyone with sharp enough eyes could spot it. Funnily enough, the secret of her shoes didn’t come out until 2013, when some of her letters were auctioned off.


A Peculiar Footwear Requirement

Those words are the exact ones written by Jackie in her letters. The way she describes her needs and wants with absolute precision is an example of how perfectly prepared she was for all the events she attended. She already knew precisely where she would use each shoe she requested.

Image: JOHN MOTTERN/AFP/GettyImages

One letter explained that she has a particular footwear requirement. “Please order me a pair of alligator shoes – size 10A – medium heel – slender – pointed toe but not exaggerated – tricky vamp business… I like elegant and timeless. I must have these for Inauguration Day so you’ll have to rush.”


Every Right to Be Demanding

This demanding side of Jackie came out when she complained about a particular shoe she did not like. “Tell [Mario] I want them in the same model as my black faille evening pumps and impress on that rather disorganized Italian that they simply must be ready in time.” These were the exact words of her complaint letter, showing just how much importance she put on her shoes.

Image: PL Gould/IMAGES/Getty Images

As a person who knew what she wanted, people might misunderstand her as being demanding. However, if you think about it, she had every right to be a little demanding because she was the First Lady of one of the most powerful countries in the world. On top of this, she was considered one of the most stylish icons of her era.


You Can’t Please Everyone

Jackie was regularly accused of caring more about fashion than about her children, her husband’s political career, or the state of the country. This just goes to show that even the most loved icons in the world can’t escape criticism.

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No matter how much good a public figure does in the world, there will always be those who wish to criticize. Jacqueline Kennedy did not escape that criticism. In fact, she learned the hard way that you simply cannot please everyone in this world.


Shh... It’s a Secret

As dazzling and perfect as Jacqueline Kennedy was, a single heel from every pair of the first lady’s shoes had to be raised by a quarter of an inch. This is a heartening thing for women to hear as it means that even the most elegant lady of that era dealt with imperfections. In the age of Facetune and Photoshop, it’s even more important for us to remember that flaws are natural  – they do not detract from your beauty or your value as a person.

Image: Bettmann/Contributor/Getty Images

Since McKeon was Kennedy’s personal assistant for a long time, it was only natural that she would have access to the first lady’s wardrobe. This was how she made her stunning discovery about Jackie’s shoes.


A Little Shorter

There is nothing wrong with imperfections – they are part of what makes us human. Jackie couldn’t change the length of her legs, but she could get elegant shoes, stack one of the heels, and get on with her duties as the first lady of the United States.

Image: PL Gould/IMAGES/Getty Images

No one would have ever guessed,” McKeon claimed in her autobiography. Essentially, the modified heels were designed to conceal the fact that one of Jackie’s legs was slightly shorter than the other while allowing her to walk comfortably. It’s impossible to tell, right? 


Meant to Be?

Coincidentally, John F. Kennedy had the same physical condition as her. Two years after their wedding, John was treated for severe back pain. The doctor found that his left leg was not the same length as his right one, and this was the source of the pain. So, JFK also started wearing a stacked heel, just like his wife!

Image: John F. Kennedy Library/Getty Images

It almost seems as though the universe was telling them that they were meant to be as they were uniquely placed to understand each other’s situation. It is unknown whether the same doctor was responsible for finding and treating Jackie’s similar problem.


Worth It!

In an interview, McKeon highlighted that Jackie’s sense of style was far from her most notable quality. “[Jackie] was more than this glamorous figure. She made me feel like part of the family.” These words from McKeon say a lot about the attitude of the First Lady.

Image: Art Zelin/Getty Images

She also shared how they became friends over the years. At the age of 19, McKeon moved from Ireland to the United States, and after her arrival, she was fortunate enough to land her long-running job with the former first lady. McKeon has no doubts that this big move away from her home country was worth it.


Part of the Family

Since the two were super close, Jackie attended McKeon’s wedding with her two kids (John Jr. and Caroline) in tow. Even after McKeon retired, Jackie kept in touch with her. She even invited McKeon and family to her home in Hyannis Harbor, Massachusetts, so they could spend summers together.

Image: Facebook/Stephanie Kauffroth Spencer

The photo above shows how close they were and how Jackie treated McKeon as part of their family. “Their everyday life would also become mine, my heart lifted by the powerful love they shared and shattered by the unimaginable tragedies they endured,” said McKeon in an interview. These words show that even in the Kennedy family’s lowest moments, McKeon was there to be with her former boss.


Jackie’s Warm Nature

“My best friend lived in Cape Cod, and whenever I would visit, Madam was always happy to see me. She would always invite me for lunch and dinner… and she would also invite me to her private beach,” McKeon said in an interview. The way she describes the former first lady is a testament to the heart Jackie had for the people around her.

Image: YouTube/Inside Edition

McKeon further reflected on Jackie’s warm nature in her memoir: “She was very shy and scared of crowds, but she had a personality that really shined when you got to know her and she opened up to you. Whenever she would meet someone, she would say, ‘Kat, what did you think of him?’ She wanted to know my reaction.” Jackie seems like the best friend we all hope to have in our lives.


Enduring Tragedy with JFK

It seems never-ending tragedies are part and parcel of being the head of state of one of the most powerful countries in the world. The image below shows one of the last few happy moments Jackie enjoyed with her husband before a shocking tragedy rocked her world.

Image: Walt Cisco, Dallas Morning News

In November of 1963, the president and the first lady were in a motorcade in Dallas when JFK was shot. He was pronounced dead shortly after arriving at Parkland City Hospital.


Retreating from the Spotlight

For instance, her close relationship with her late husband’s brother, Robert Kennedy had some people theorizing that it was a romantic relationship. However, no one knows what really happened there as the two never spoke of having any romantic connection. Instead, Jackie shook the world when she got married again in 1968 to a shipping tycoon from Greece –  Aristotle Onassis.

Image: Central Press/Getty Images

Following JFK’s assassination, Jackie retread from the spotlight. She avoided the eyes of the public to such an extent that she became something of a recluse. However, there were still plenty of headlines about her personal life.


The Island of Skorpios

Aristotle Onassis was rich enough to own a private island – Skorpios. This was where Jackie and Ari held their wedding ceremony in 1968. This island remains a fascinating mystery to this day.

Image: YouTube/ Drone Tv

Located in the Ionian Sea, Skorpios is one of many Greek islands. It lies to the west of mainland Greece and east of Lefkada island. It covers an area of 205 acres, comprising sandy beaches and thick forests. It could have been a tourist spot for foreigners and locals alike, but Onassis changed all of that. 


Ari’s Take on Skorpios

Ari had a lot of plans with regards to the rehabilitation of the Skorpios. He bought the land for 3.5 million drachmas, which is the equivalent of around $12,000 in today’s US currency. That’s right – $12,000 could buy you an entire island in 1963.

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After buying the island, Ari imported more than 200 types of trees to Skorpios. He ensured the island was able to have rich woodlands and also created East Beach with sand imported from Salamis Island, also in Greece.


Jacqueline Onassis

Aristotle and Jackie decided to tie the knot on this island, making Skorpios famous worldwide. The Greek businessman and the former First Lady of America had been friends for many years before tying the knot. However, romance only developed between the couple after the deaths of Jackie’s first husband, John F. Kennedy, and her brother-in-law, Robert F. Kennedy.

Image: Bettmann/Contributor/Getty Images

Understandably, the assassination of JFK made Jackie fearful for her family’s safety. Following Robert Kennedy’s death in 1968, Jackie said, “If they’re killing Kennedys, then my children are targets.” As a concerned mother, the welfare of her children was Jackie’s priority, which is why she set her mind on getting out of America and settling down somewhere else.


The Security She Needed

Moreover, even though Ari was mega-rich at the time, their wedding was small and intimate, having only approximately 40 guests who were family members and close friends of the couple. They had a Greek Orthodox traditional wedding, and Jackie’s children – Caroline, and John Jr. – were involved.

Image: Bettmann/Contributor/Getty Images

Fortunately, Jacqueline found the security she was seeking with her second husband, Aristotle, also known as Ari. They got married in October of 1968. They may have had a huge age gap when they tied the knot, but it seems that they loved each other very much.


Risqué Photos of Jackie

After Ari and Jackie’s wedding, the island became world-famous. However, with this fame, the couple’s privacy was lost. In 1971, Jackie was photographed sunbathing naked on one of the private island’s beaches. The image was published in Italy in 1972, provoking outrage in the US.

Image: Ron Galella/Ron Galella Collection via Getty Images

Settimio Garritano was the photographer responsible for taking the photograph of the former First Lady. The photographer conned his way onto the island by pretending to be a gardener. After learning that Jackie sometimes sunbathed naked, he snuck around until he could get a good shot of her in this incredibly private moment.


Italian Paparazzo

From his position, he watched Jackie undress until she was completely naked. In 2009, the photographer said that he wanted to get the shot because he didn’t believe the former First Lady really sunbathed naked. “It didn’t seem possible,” he said in an interview.

Image: Ron Galella/Ron Galella Collection via Getty Images

Garritano found it difficult to sell the pictures of Jackie. Reputable publications refused to print them. However, later in 1972, he was able to sell them to men’s magazines and they had soon traveled the world, even appearing in Hustler.


Was Jackie a Bringer of Bad Luck? 

It seems that the photograph was not the only scandal that Jackie would attract. She has also been connected to the Kennedy curse. Aside from the assassination of the brothers, John and Robert, many unfortunate events befell the Kennedy family.

Image: Bettmann/Contributor/Getty Images

Because of this, Jackie was accused of transferring the bad luck to the Onassis family by marrying Aristotle. This superstition was believed by Christina, Ari’s eldest daughter, and she only became more convinced when her mother (Ari’s ex-wife) died in 1974 following an alleged drug overdose.


The Bad Luck Continues

Aside from the death of the billionaire’s ex-wife, the bad luck continued when the family business fell into financial difficulties. At the same time, Aristotle’s health began to decline. Soon enough, even Aristotle began to believe that the woman he loved may have brought some kind of curse into his family.

Image: Hulton-Deutsch Collection/CORBIS/Corbis via Getty Images

With this, Aristotle looked into filing for divorce, and also, he changed his last will and testament to reduce the total amount Jackie would receive when he passed on. As we’re about to learn, he reduced her inheritance by a staggering amount.


Jackie Fought for It

When the shipping magnate died in 1975, Christina, his eldest, was the sole heir. Most of the family business, financial aspects, and also the properties were given to Christina.

Image: Keystone/Getty Images

However, Jackie did not just accept this – she fought for what she saw as rightfully hers. After years of negotiations, she was able to get a $26 million settlement from Christina. Meanwhile, Aristotle’s remains were laid to rest on the island of Skorpios, where his son also lies.


The Death of Onassis

After the death of her second husband in 1975, Jackie returned to work. She became a consulting editor for a publishing company called Viking Press and later, an associate editor for Doubleday, a publishing company in America. Since she loved what she did in the White House, she continued her architectural and cultural preservation work.

Image: National Archive/Newsmakers

Jackie may have lost loved ones, but she continued to do what she loved to do. At times, it was a struggle to go back to her life, but Jackie did not give up. Sure, she had a lot of challenges during her life, but she was able to rise up and carry on each time, no matter what was thrown at her.


Jackie’s Style Evolution Continues

Despite the criticism received by the First Lady, she forged on, continuing to be a style inspiration to every woman in the world. That is why in 2013, a pair of Jackie’s pumps designed by Rene Marconi, a well-known Italian designer, was auctioned in Los Angeles.

Image: Corbis via Getty Images

The size 10 shoes were sold to an anonymous person for almost $30,000. This gives you an idea of the amount of money some people would give just to be a style icon like Jacqueline Kennedy.


Jacqueline: A Phenomenal Woman

In 1993, Jacqueline fell from a horse. This was likely one of the reasons why her health started to decline. Jackie was later on diagnosed with non-Hodgkin lymphoma. By May of 1994, the disease had affected her liver, brain, and spinal cord. In that same month, Jacqueline passed away in her sleep at the age of 64.

Image: David Cairns/Express/Getty Images

Jacqueline Kennedy Onassis lived a wonderful and amazing life. She was a woman of style and substance. The memories of her are still living in the hearts of her children, her loved ones, and close friends like McKeon.


The John F. Kennedy Library Contains Some of Jacqueline’s Clothes

The John F. Kennedy Library houses many of the famous outfits of the former First Lady. It’s a fascinating exhibit, displaying the pieces that Jackie wore during her time at the White House. The preserved outfits offer a chance for the present and future generations to see one aspect of what was so inspiring about this iconic woman.

Image: PL Gould/Images/Getty Images

In 2001, the Metropolitan Museum of Art in New York also presented several works at an exclusive exhibition entitled, Jacqueline Kennedy: Years of the White House. However, the true secret of Jacqueline’s shoes was only revealed in McKeon’s autobiography. Who would’ve though it would take 19 years after her passing for her secret shoe dimensions to be uncovered. It was Jackie’s well-kept secret.