Ranking The Kennedy Women’s Best Wedding Dresses By Timeless Appeal

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The Kennedy dynasty left a permanent mark on the American psyche. In the fashion world, their legacy has manifested through figures like matriarch Jacqueline Kennedy Onassis and ’90s it-girl Carolyn Bessette-Kennedy, who set sartorial trends for the rest of the country. When it comes to the bridal fashion lookbook of the presidential family, these women had a choice to make as the world watched closely: cement their style prowess and meet the trends of the era, or opt for something classic and timeless, as fitting for American royalty. 

Every bride shines on her big day, but as the years go on, some wedding gowns age better than others. Those who meet the demands of the “what’s hot” fashion charts might win style points in the moment, but the appeal of those en-vogue silhouettes tends to lessen as time flies by. Meanwhile, gowns that prioritize eternal bridal elements, whether it’s a fairytale aesthetic or a classic hemline, tend to go down in history, especially in a family like the Kennedys. Princess-style ballgowns and their minimalist slip-style equivalents will echo through the ages, while those that rely on decade-specific crazes (hello, ’80s puffy sleeves), often seem dated in hindsight. The “anti-bride” wedding trend of 2023, for example, probably won’t impress future generations with its laid-back feel. 

As far as unconventional celebrity wedding dresses that left a mark on us go, the Kennedy women played it pretty safe with their nuptials. Some, like Caroline Kennedy, leaned more on trends and combined them with unique and timeless details to strike a balance. Then we have Carolyn Bessette-Kennedy, whose sleek classic gown matched her simple yet chic beauty looks perfectly.

The eldest child of John F. Kennedy and Jacqueline Kennedy Onassis, Caroline Bouvier Kennedy tied the knot in 1986 with artist and designer Edwin Schlossberg. The pair met at the Metropolitan Museum of Art, and given that Caroline is the only daughter of the former president, their nuptials attracted significant media attention. We’re ranking her Carolina Herrera gown at number four because of the way it fused together classic elements with trends of the era.

Featuring a drop waist, short puffy sleeves, and a 25-foot train, the dress, which was worn to Caroline’s ceremony at Our Lady of Victory Church on Cape Cod, Massachusetts, remains a firm example of ’80s design. Some celeb outfits from the ’80s look even cooler today, but those staple design details do tend to cement a dress firmly in its era rather than giving it a timeless quality. However, Caroline’s dress had unique and classic details, too, including the silk organza fabric, the rounded neck, and the shamrock embellishments on the bodice, which were a nod to Caroline’s Irish background. “I loved the shamrocks on her dress in honor of her Irish heritage,” one Instagram user noted. “I never knew this dress catapulted Carolina Herrera to global fame.” 

Of course, when you consider other famous wedding dresses of the decade, Caroline’s might even be considered muted. Take Princess Diana’s enormous taffeta creation, for example, or Julia Louis-Dreyfus’ gown that was adorned with ruffles, puffs, and lace. Caroline’s daughter Tatiana Schlossberg followed in her mother’s footsteps for her 2017 wedding, wearing her own Carolina Herrera creation. There’s no question that the late environmental journalist was a celebrity kid who inherited her parents’ famous style.

In 2014, “Curb Your Enthusiasm” star Cheryl Hines wed Robert F. Kennedy Jr., nephew of the 35th president John F. Kennedy. Perhaps partially influenced by her background in Hollywood, Hines’ dress had some of that classic feel that you’d expect of a Kennedy wedding, combined with a contemporary edge. The designer of the tea-length strapless frock, Romona Keveza, revealed to People that it reflected Hines’ “timeless, modern style.”

While tea or waltz-length silhouettes are often associated with more casual or outdoor weddings, this design has actually been used for decades, which helped Hines to evoke that sense of timelessness. “Tea length was really popular with wedding dresses in the 50s-60s and I think they’re adorable!” one Redditor commented on the dress style, while another added, “I actually think they’re fun and have a bit of a beautiful vintage vibe to them!” The strapless element is what brings this look into the 21st century.

Aside from the shorter hem, the simple dress was made from pearl-beaded fabric, which poetically channeled RFK Jr.’s aunt Jacqueline Kennedy Onassis. “It’s very quintessential Jackie,” Kennedy family social secretary Letitia Baldrige said about the fabric when researching for her book “Legendary Brides” (via People). Keveza told the outlet that she used the fabric to make the strapless, tea-length dress on a whim, and Hines happened to fall in love with it. “It’s interesting how it came full circle, [with] Letitia Baldrige, who knew Jackie so well and thought that fabric was very perfect for Jackie,” Keveza added. “I feel it’s almost as though Jackie was there at her wedding, giving her blessings to Cheryl who was wearing a dress inspired by her, and to Robert Kennedy, Jr. It’s quite magical in many ways.”

Nearing the top of our list is Jacqueline Kennedy Onassis, for her wedding to John F. Kennedy on September 12, 1953, at St. Mary’s Church in Newport, Rhode Island. Still Jacqueline Bouvier at the time, the former first lady was a vision in the “Beauty and the Beast”-coded ballgown. Created by Ann Lowe, who also made Jackie’s bridesmaids’ dresses, the gown featured a portrait neckline, pleated bodice, oversized rosettes, a bouffant skirt and a scalloped hem, and was created with 50 yards of ivory silk taffeta. Along with a traditional blue ribbon hidden in her underskirt, Jackie dazzled in accessories, including a rosepoint lace veil passed down to her by her grandmother, a diamond bracelet, a pearl choker, and fittingly, a tiara.

The ballgown silhouette was popular in the 1950s, along with the fitted bodice. However, the former FLOTUS cast aside other trendy elements of the time, including a sweetheart neckline, in favor of details that gave the look an eternal princess vibe, such as the floral embellishments and portrait neckline. Even with the more minimal or risqué dress styles on the market today, some brides will always flock towards this fairytale style. 

Legend has it that Jackie actually wanted a more low-key dress for her big day, where she was greeted by 600 guests at her ceremony and 900 at her reception. But JFK’s father, Joseph Kennedy, wanted her in something more extravagant. Imagine your father-in-law having the final say on your wedding dress! Ann Lowe was eventually commissioned by Jackie’s mother, Janet Lee Bouvier, for the gown, and was rightfully disappointed when Jackie later told the press it was simply the work of “a colored dressmaker,” per Elle.

The over-the-top energy of 1980s fashion persisted well into the ’90s, and many celebrity wedding dresses followed suit. But one bride who stood her minimalist ground in the face of all those trains, voluminous skirts, and sparkly embellishments was Carolyn Bessette-Kennedy. It’s no wonder that she was later crowned a style icon; her delectably simple gown resisted the maximalist trends of the era and has stood the test of time as a classic. It may have also helped to steer fashion in the second half of the decade to its more minimal sweet spot. 

Carolyn wed John F. Kennedy Jr. on September 21, 1996, on Cumberland Island, Georgia. She met the designer of her gown, Narciso Rodriguez, at Calvin Klein, where she worked as the P.R. director. The gown was made of pearl-colored silk crepe, featuring a bias-cut, floor-length silhouette, and was reportedly worth $40,000. It tops our list because Carolyn embraced her subdued style rather than bowing to the bandwagon, and actually paved the way for an everlasting aesthetic that minimalist brides would return to for decades. “Her style was never a production,” Rodriguez told Elle in March 2025. “It was just something innate. Even when she wore the most complicated Yohji [Yamamoto] piece, it was natural.” Meanwhile, Carolyn’s industry colleague Ann Mashburn noted to Harper’s Bazaar, “The simplicity of it was so of-the-moment and so her … She just wore a beautiful dress that was like her, and I think that’s inspirational. She really was just herself, and, you know, was pretty cool about it.”

Because Carolyn was true to her sense of style, future brides who didn’t resonate with the Jackie Kennedy-style Disney gown now had their own blueprint of what Vogue describes as “cool girl” style.

To rank the wedding dresses of the Kennedy women, we focused on which dresses incorporated elements of the trends of their eras, and which went their own way to create a look that was everlasting. All the gowns were stunning and each bride shined in her own way, but Carolyn Bessette-Kennedy’s sleek minimal number broke the princess-dress pattern with its simplicity, and has gone down in history ever since.