The Kennedy Women's Wedding Dresses, Ranked From Worst To Best

There was once a time when some of the most famous people in the world had the last name Kennedy. The political family's generational reign still shows up in politics and pop culture. Many people who witnessed the Kennedys before and during the Camelot years and beyond have seen them indulge in glamorous events. Some of the most extravagant events happened when the Kennedy men and women decided to bring one special someone into the fold through marriage.

Much like their winning streak in politics, the Kennedys have historically been known for throwing a good party. So, when the time comes for a Kennedy to have a wedding, it's sure to be an event that is photographed and talked about long after it is over. But at the center of each lavish Kennedy wedding is a woman waiting to walk down the aisle in a stunning wedding dress. In many cases, the bride was in a couture gown that is still being discussed today. While some of them are being talked about for getting it right, there are a few Kennedy women who got their wedding looks totally wrong. Here are some of the worst and best Kennedy wedding dresses of all time, starting with the worst.

The Kennedy family tree includes Sydney Maleia Kennedy Lawford. She was born on Aug. 25, 1956, to 35th U.S. President John F. Kennedy's sister, Patricia Kennedy Lawford, and British actor Peter Lawford. On Sept. 17, 1983, Kennedy Lawford married television producer James Peter McKelvy. While many faces from her famous family attended her ceremony in Cape Cod, Mass., including her aunt, Jacqueline Onassis Kennedy, and cousins Caroline and John F. Kennedy, Jr., her dress unfortunately left much to be desired. Kennedy's gown of choice was riddled with lace, a flower crown, and, to make it even more 1980s-coded, had extremely high shoulder pads.

Although high shoulder pads were a sign of the times during the era of her wedding, Kennedy Lawford's wedding gown was one of the family's most legendary fashion flubs. The dress did nothing for her figure and seemed a bit too mature for the then-27-year-old bride. Sure, no one was expecting a slip dress, but this was by far the worst Kennedy wedding dress of all time.

Maria Shriver may be a Kennedy, but in 1986, she became Mrs. Terminator. Born to Eunice Kennedy Shriver, John F. Kennedy and Robert Kennedy's sister, and Sargent Shriver on Nov. 6, 1955, Shriver was a rising journalist when she met her then-future husband, Arnold Schwarzenegger, at a charity event that was held at her mother's home. They married on April 26, 1986, at a star-studded event that, according to Schwarzenegger, included Grace Jones and the late Andy Warhol, who arrived late to the function.

"He came to the wedding," the former California governor recalled in an interview with People. "He was a master of attention, getting attention. We were in the middle of the wedding, and Maria and I were standing out there about to say, 'I do' and the whole thing."

During her big day, Shriver wore a muslin silk and lace Marc Bohan gown. The lace covered her neckline, shoulders, and abdomen as the silk flowed across her waist. Shriver's dress was befitting for a mid-80s wedding. However, it would be better as a Halloween costume today. Still, her wedding was iconic, though Shriver and Schwarzenegger ultimately divorced in 2021, 10 years after her initial divorce filing.

The Kennedy family has endured its share of heartbreak over the decades, and the assassination of Robert F. Kennedy in 1968 remains one of its most devastating tragedies. While the world, especially those in the U.S. who were supporting his presidential run, were shocked by his tragic death, his loss was felt on a deeper level by his wife, Ethel, and their 11 children. Five years after the tragedy, a happier memory came for the family when his eldest daughter, Kathleen Kennedy Townsend, married David Lee Townsend in a lavish wedding in Washington, D.C. The wedding was held in November 1973 and included 160 guests. 

According to The New York Times' feature of the wedding, Kennedy Townsend's uncle, Sen. Edward M. "Ted" Kennedy, walked her down the aisle, along with Caroline Kennedy, Courtney Kennedy, Kerry Kennedy, and Jean Kennedy Smith as her bridesmaids. Kennedy Townsend wore a white, floral gown with a matching crown and shoes. The dress's style fits the bohemian fashion trend of the 1970s and the elegance of a Kennedy wedding. However, it might have been a bit dull and mature for a young bride.

The early 1990s were all about continuing the gaudy trends and patterns of the 1980s, especially during wedding season. During the decade, many brides continued opting for lavish weddings and big gowns, and Kerry Kennedy was no exception. In 1990, Robert F. Kennedy's daughter married former New York governor Andrew Cuomo. According to UPI, their wedding took place at St. Matthew's Cathedral in Washington on June 9, 1990.

For her and Cuomo's wedding day, Kennedy channeled her inner Princess Diana by adding a long and flowy veil to the look. But what brought the dress down was its tablecloth-like hem pattern. To make the look even worse, Kennedy found a pair of shoes to match the hem's pattern. The lawyer likely didn't intend to choose a dress that could've been a tablecloth or curtain, but that's exactly what her dress gave.

In 1982, long before his own lane in politics, Robert F. Kennedy Jr. married his first wife, Emily Ruth Black. According to The New York Times, RFK met Black while they were both students at the University of Virginia School of Law. The couple married in a Protestant church in Bloomfield, Ind., where Black was baptized. In their wedding photos, the United States Secretary of Health and Human Services's bride wore a long-sleeved, floral dress with sheer fabric covering her chest and arms. The simple yet elegant dress fit the couple's 500-guest church wedding, filled with their family and friends.

Unfortunately, the couple, who share children Robert Kennedy III and Kathleen "Kick" Kennedy, divorced in 1994 after 12 years of marriage. Hopefully, Black has fond memories of her chic wedding dress, even if she and RFK didn't last.

Activist and Special Olympics founder Eunice Kennedy Shriver wore this wedding gown when she married Sargent Shriver on May 23, 1953. The ceremony took place in New York City and included Kennedy Shriver's prominent family. The Dior dress reflected the conservative, yet tamed elegance of the early 1950s. However, when her granddaughter, who is also named Eunice Kennedy and was born to Eunice Sr.'s son, Anthony Shriver, wore the gown on her 2020 wedding day, she added a modern twist. 

According to Vogue, Eunice Jr. worked with Miami-based luxury bridal boutique Ever After Miami to update the gown to fit her aesthetic. She made the dress strapless and added a new matching bodice with a matching veil. Although Eunice Jr. said the dress had turned colors and had some holes in it due to it being over 50 years old at the time, she knew wearing it was the perfect way to honor her family's legacy. "My grandmother wore [the dress] at her wedding to my grandfather on May 23, 1953, and 67 years later, I wore it to marry Mikey," Eunice Jr. told Vogue. 

Many Kennedy aficionados who were around in the '80s anticipated Caroline Kennedy's wedding day. The only daughter of President John F. Kennedy and Jacqueline Kennedy Onassis tied the knot in July 1986. According to Vanity Fair, the wedding took place in a small church in Cape Cod, Massachusetts, and included more than 2,000 guests. For her big day, Kennedy wore a wedding dress designed by Carolina Herrera. The white silk organza gown included the classic '80s puff sleeves and a massive skirt that flowed at the bottom. 

Kennedy's wedding dress was absolutely fitting for the era in which she married. However, though it showed the excessive flair of the '80s, she made it a fashionable moment in history. So much so that the wedding gown put Herrera on the map as one of the most sought-after wedding gown designers in the world today.

In 1956, John F. Kennedy's sister, Jean Kennedy, married Stephen Edward Smith. The ceremony was held in New York City that May and was attended by many of the Kennedy family's elite. During a time when her siblings were forging political careers of their own, with the wedding happening five years before JFK's presidency, her wedding could've been compared to the royal family, and she matched the elegance of one of the royals' most prominent members — Queen Elizabeth II.

Kennedy's crowned veil on her wedding dress was quite similar to the one Queen Elizabeth wore during her wedding to Prince Philip on Nov. 20, 1947. The veil, as well as Kennedy's gown, showed many elements of 1950s couture, which was all about structured tailoring, feminine shaping, and meticulous detailing. Kennedy's decision to wear a dress that was simple yet complemented her frame makes her wedding day one of the best among the family. 

While Robert F. Kennedy Jr. has been married three times in his life, he seemingly found his forever person in his third wife, actor Cheryl Hines. The "Modern Family" star married into the Kennedy family on Aug. 2, 2014. Their wedding was held at the Kennedy compound in Hyannisport, which, according to Hines' 2024 Instagram post, wasn't their initial plan and was suggested by RFK's mother, Ethel, who died in October 2024. "[I] told her we were going to go to City Hall and get married and she said, 'Well don't you want to get married here (In Hyannis Port) so we can all be a part of it?'" Hines recalled in her post. "We talked for a long time and she convinced me to have a small wedding there. It was perfectly imperfect."

On her big day, Hines wore a strapless Romona Keveza gown with a short skirt. The dress was simple and accentuated her body well. It was also a less conservative wedding look than what RFK Jr.'s first wife, Emily Ruth Black, wore for their wedding. However, that was likely due to how trends evolved between the two weddings. 

As the daughter of former governor Andrew Cuomo and Kerry Kennedy, Mariah Kennedy-Cuomo was born into not one, but two political families. On July 20, 2024, both families joined forces to celebrate her wedding to Tellef Lundeval. The bride stunned in a Vera Wang strapless gown with floral lace. The modern wedding look also included Kennedy Cuomo wearing flowing loose curls without a veil. Kennedy Cuomo's wedding dress was one of the many ways she matched the elegance and somewhat excessiveness of a Kennedy wedding. 

According to Vogue, the ceremony was held at the Kennedy Compound in Cape Cod, Massachusetts, where Kennedy patriarch Joseph P. Kennedy Sr., his wife, Rose, and their nine children — including U.S, President John F. Kennedy and senators Robert Kennedy and Edward Kennedy — all lived.  Kennedy Cuomo also honored one of the family's traditions of having a massive wedding cake at the wedding. According to People, the couple included an 8-foot wedding cake that required her to get on a ladder to reach the cake's highest tier. However, the possible injury-inducing cake was worth it, as Kennedy Cuomo recreated a tradition that was introduced by Eunice Kennedy for her 1953 cake. Maria Shriver also recreated her mom's cake during her and Arnold Schwarzenegger's 1986 wedding. 

Jackie Kennedy Onassis's life was forever changed when she married John F. Kennedy. Their wedding was one of the most highly anticipated events of their time, and the couple didn't disappoint. According to the JFK Library, over 800 guests celebrated the couple and witnessed the bride's intricately crafted wedding dress up close. Kennedy Onassis wore a dress made of ivory tissue silk with a portrait neckline, fitted bodice, and a bouffant skirt embellished with bands of more than fifty yards of flounces. She also accessorized the look with a choker of pearls and a diamond bracelet that JFK had gifted her ahead of their big day. 

Kennedy Onassis's wedding gown remains iconic over seven decades after she married her first husband and the father of her children. Her decision to tap Ann Lowe, who, according to the National Museum of African American History and Culture, was among the first nationally recognized Black fashion designers, to create her now-legendary gown helped cement its place in fashion history.

On July 13, 1991, Robert F. Kennedy and Ethel Kennedy's son, Maxwell "Max" Kennedy, married Victoria Strauss. The couple married at Cathedral Basilica of Saints Peter and Paul in Philadelphia, Pennsylvania, surrounded by their family and close friends. On their wedding day, Strauss wore a gorgeous floral wedding gown with florals at the top and hem of the dress. The detailed flowers on the top of the dress created a romantic bridal look as she married the love of her life.

Strauss's wedding dress was designed by a then-little-known fashion designer named Vera Wang. While discussing the opportunity to design her first wedding dress for one of the most famous families of all time, Wang recalled ensuring Strauss had all of her flowers that day. "We worked on that dress and I'd only been in business, I think, two months," the designer told Entertainment Weekly. "It was my Kennedy wedding....We really, really worked hard on that dress. The whole hem was hand-rolled organza flowers. And all I remember is that — I didn't go to the wedding — but I heard that as soon as she got out of the church, in true Kennedy fashion, they were playing touch football and the whole hem got grass stains all over it."

Though there are many Kennedy weddings to discuss, the conversation surrounding the best wedding dress of all time from the family's lineage goes to Carolyn Bessette Kennedy. CBK's style has become legendary in the years following her, her husband John F. Kennedy, Jr., and her sister Lauren Bessette's untimely death following a fatal plane crash that occurred with Kennedy, Jr. behind the wheel. One of her most notable looks came during her and JFK Jr.'s 1996 ultra-private wedding on Cumberland Island in Georgia. The dress was designed by Bessette Kennedy's close friend, Narciso Rodriguez, who, at the time, was an up-and-coming designer who worked with her at Calvin Klein. 

The slip dress pulled away from the classic, extravagant bridal gowns the Kennedy women had become known for. Bessette Kennedy opted to choose a dress that was attuned to the slip dress trend of the 1990s. Though she would pass away just three years after she and JFK Jr. said "I do," the impact of what Vogue deemed a "cool girl" dress has been recreated by new generations of fashionable brides.