Ranking The Kennedy Women's Best Street Style Moments By Timeless Appeal

Each first family has influenced the United States to some degree, but at least when it comes to fashion, the Kennedys were the crème de la crème. The women in the prestigious circle are often synonymous with elegance, and while we most often discuss their looks in relation to formalwear and working wardrobes, their street style is also worth studying for fashion enthusiasts — especially if your goal is to curate a timeless aesthetic of your own. 

When John F. Kennedy became president in 1961, his wife, Jacqueline Kennedy Onassis, set a new sartorial standard in the White House, giving new meaning to the idea of "first lady glamour" with her skirt suits and refined pillbox hats. Thirty years later, her daughter-in-law Carolyn Bessette-Kennedy followed in her footsteps, only this time through a minimal aesthetic rather than one that was overly luxurious. You might think of street style as the comfiest clothes you can get away with in public, but both of these women were a little more intentional than that. All these years later, they deserve recognition for the way that they carried over their style ethos even after clocking out.

While Jackie in particular was a product of her time, she did occasionally reach for outfits that were ageless in their detail, turning to staples that could more or less be worn in any decade. And as for Carolyn, one Reddit user described her perfectly: "She wore classics. She was in style then and she would be just as in style now." All of their following street style looks are timeless to some extent, but we ranked them based on which are the most classic of all, concentrating on which outfits could truly still land decades later.

Jacqueline Kennedy Onassis was most known for her sophisticated first lady style. Even six decades later, she's remembered for her satin gowns and Chanel suits. But photos of her street style, most often from her life after the death of John F. Kennedy in 1963, show a slightly different aesthetic. The former FLOTUS always carried an air of elegance and inherent fashion sense which even came through in her off-duty looks, but these usually featured quieter pieces than monochrome pink tweed. 

In October 1970, she was photographed in London, England, with her sister Princess Lee Radziwill, who resided in a townhouse just behind Buckingham Palace at the time. Jackie blended her untamable elegance with a more laid-back energy, wearing an outfit consisting of a white minidress and a black coat draped over her shoulders. The dress was cinched in by a belt at the waist so that it could have been a skirt, while the top of the garment had a classic rounded collar. The former first lady fended off the fall chill with the short coat that was just the right length to balance her skirt. Both of these pieces could fit into the 2020s (after all, the little white dress was the fashion trend to have on your radar in spring 2024), though street style today tends to be less glamorous. 

The elements that do date this look are the heeled loafers and the teased volume in her hair. Loafers are still popular today as the one shoe that will always dress up leggings, but pairing them with a minidress and draped coat would come off as exceptionally preppy and vintage-coded. When Jackie wore this ensemble at the beginning of the '70s, it was just her style. 

Although she had plenty of first lady looks that sparked fashion movements, Jacqueline Kennedy Onassis toned down her aesthetic even more when she was snapped out and about on the streets of New York City. We'd never expect to see her in jeans, but she did have a collection of pants and shirts that helped cultivate a street style that was refined, practical, and pretty timeless.

Though she was a woman who loved vibrant color, she looked chic in this all-black 'fit — a monochromatic outfit that could still inspire your one-tone looks today (more or less). The photo, taken circa 1970, shows Jackie in a basic slim-fitting shirt with mid-length sleeves worn with black straight-leg pants. Black monochrome still has a time and place today, and the slacks and shirt themselves could come from any decade, though the long pointed collar does distinctly point to the '70s. Jackie further grounded this ensemble in its decade with accessories, including a statement necklace and oversized sunglasses (which you can learn how to style here).

While glasses that covered half of your face were popular in the '70s, the silhouette has ebbed and flowed between the "hot" and "not" lists in the decades since. The same goes for the bold necklace. These pieces were very contemporary, but maximalists run back to them every few years, as we saw when our favorite '70s trends had a resurgence in 2023. Overall, you might say this New York City look was classic with a modern edge, but stylish nonetheless. As one Instagram user summed up the former first lady's sartorial energy: "Always so chic."

Carolyn Bessette-Kennedy had a simple yet chic beauty look, and she maintained that energy 24/7. She would dominate any list of timeless style icons, even if we weren't narrowing it down to the Kennedy women. And photos like this one, taken in 1996 when the newlywed was walking her dog after her honeymoon, demonstrate why that is. "Could be today," an Instagrammer commented beneath the photo.

There's nothing overly exciting going on here, but that's exactly why Carolyn's style still resonates 30 years later. It might not be your go-to style for dog-walking given the block kitten heels and denim, but her black sleeveless top and simple straight jeans are timeless staples. If you're looking to build a capsule wardrobe, it's pieces like this that are worth investing in. The clean lines are one reason that this look could be copy-pasted into any era — there's no recognizable 2010s skinny silhouette or 1970s flare to date the denim, and the same goes for the muted top. But the color palette also makes this look a classic; the combo of black and medium-wash denim always worked, and always will work. "One could walk down the street wearing her style today and still be seen as stylish," one Reddit user explained of Carolyn's overall aesthetic. "Her style is timeless and will still be copied for decades to come."

The kitten-heeled strappy sandals are perhaps the only part of this 'fit that reminds us this photo was taken in the '90s, even if there's no cuff on the jeans. Though cuffs were popular at the time, Carolyn resisted the urge to jump on the bandwagon and instead stuck with the subdued straight-leg form that could seamlessly fit into any time period.

As one Reddit user described Carolyn Bessette-Kennedy's style, both on and off the street, "She wore black, white and beige. We all dressed that way in NYC in the ['90s]." Another fan replied in the thread, "There's a reason this style is often called timeless." The photo that sums up this immortal off-duty aesthetic was taken in October 1996, on the streets of New York City. 

Carolyn teamed a classic white tee and medium-wash bootcut jeans with black boots and a black trench. Her accessories were slightly '90s-coded, but are minimal; unlike Jacqueline Kennedy Onassis' statement '70s pieces, the tortoiseshell headband and the oval sunglasses are simultaneously '90s trends and eternal staples. Looking at this ensemble, you might describe it as '90s minimalist, especially as the denim silhouette was popular in the decade. But still, you could wear this exact ensemble down the street in the 2020s and no one would bat an eye. "Every one of these pieces would be perfect for today," an Instagrammer confirmed. "That is timeless."

Additionally, going for a black coat rather than the traditional beige was a nice touch that spoke to Carolyn's styling prowess; beige would have worked well, but the black completed the color story told by the boots, scarf, and sunglasses, while also contrasting against the white for a slightly more memorable result. That's why this look tops our list — it's truly ageless, despite containing accessories that were popular at the time she wore them, and that makes it a genuine representation of Carolyn's overall style. Her clothes were so simple and classic, and yet she clearly knew what she was doing.

Figures like Carolyn Bessette-Kennedy and Jacqueline Kennedy Onassis had a natural inclination towards lasting style, so picking their best off-duty looks wasn't easy. We considered each piece of their street outfits, from garments to shoes to jewelry, and assessed how they either dated the outfit or made them last. Carolyn's final trench coat ensemble was the perfect example of a look that could be dropped into any decade and would still be considered stylish without any updates.

Next, check out our ranking of the Kennedy women's wedding dresses, which were also brimming with timeless appeal.