The Kennedy family has always captivated the world with their charm, poise, and timeless sense of style. At the forefront of their fashion legacy are Jackie Kennedy and Caroline Bessette-Kennedy, two women who redefined elegance in their respective eras. Jackie’s impeccable wardrobe as First Lady made her a global fashion icon, while Caroline’s minimalist yet striking aesthetic became the epitome of 1990s chic.
Together, their fashion choices tell a story of sophistication, grace, and individuality that continues to inspire designers, influencers, and everyday wardrobes. In this post, we’ll dive into the signature styles of these two icons and uncover what makes their fashion influence so enduring.
Jackie Kennedy
Born in Southampton, New York on July 28th, 1929, Jacqueline Lee Bouvier who was later known as Jackie Kennedy had an accomplished and privileged early childhood. She went back and forth between Southampton and Fifth Avenue in New York, won horse riding competitions by age 11 and loved to read. According to the JFK Library, one of her teachers thought Jackie was “a darling child.”
Jacqueline began working for the Washington Times-Herald newspaper in 1951 as a photographer taking pictures of anyone and everyone she met, would ask them questions of the day and then would put this into her newspaper column and during this time, she met John F. Kennedy. At the time, he was going to be elected as senator for Massachusetts and in September 1953, they married. It wasn’t until 1960 that JFK announced he would run for president and soon he started going all over the world with Jacqueline by his side.
She officially became the first lady at 31 years old and this was when more eyes were on her elegant yet classy style. Her personal style during this time reflected her passion for all things education and art and she truly prioritized her new role as first lady. Jacqueline was full of grace, elegance and intelligence while working to make the world better and captivated the world unlike no other.
Jacqueline’s style was tailored suits, classic colors, pearls, sleeveless dresses, white gloves, round sunglasses and more. Below we’ve attached some of her most iconic, chic looks plus some things you can learn from her style if you’re looking to upgrade your wardrobe.
Choose thoughtful accessories and a cohesive color palette
Through Jackie’s outfits, you can see that she wears soft, neutral tones and sometimes pops of pastel. All of these really capture and exude that sophistication. Building a cohesive wardrobe that has complimentary colors to you can make any outfit look clean and put together.
We must not forget about the power of accessories. Whether she is wearing pearls, a simple pair of round sunglasses or adding white wrist-length gloves, all the accessories compliment the full look. Statement accessories can add personality and polish to your outfit.
Opt for tailored pieces
We know the feeling of clothes not fitting us right and how it can throw off an outfit completely. Jackie always had perfectly fitted clothes that emphasized her silhouette and this created that polished appearance she always had. Whether she was going for a simple evening gown or a two-piece matching set, having tailored outfits was always a must. Prioritize your own fitted clothing and don’t be afraid to alter them.
Having effortless confidence
Anyone can style a piece, but at the end of the day, it’s about confidence and how you feel wearing your looks. Confidence is the most essential to any style and Jackie always carried herself with grace and elegance which perfectly matched her outfits. Cultivate your own sense of confidence because how you wear an outfit is just as important as the outfit itself.
By adding some of these fashion principles and confidence tips into your style or day to day life, you can start to embody your own elegant and modern wardrobe just like how Jackie did.
Carolyn B. Kennedy
Born on January 7th, 1966 in White Plains, New York, Carolyn Bessette Kennedy always wanted a private life and never dreamed of being famous. However, she is widely known for her iconic looks in the fashion world because of how simple yet chic she always looked. Carolyn was the wife of John F. Kennedy Jr. but tragically passed away in the summer of 1999 in a plane crash off the coast of Martha’s vineyard with her husband and her sister Lauren.
Later on in life, Carolyn grew up in Greenwich, Connecticut, went to Boston University and then moved to New York in 1989. While working retail for Calvin Klein in Boston, Susan Sokol who was the president of Calvin Klein women’s wear at this time, “discovered” her and gave her a job in celebrity sales. In 2023, Sunita Kumar Nair published a biography on Carolyn Bessette Kennedy and in this book, Sokol says “It was so obvious she had a great sense of style and stood out from the rest.”
While working at Calvin Klein, she noticed how wealthy clients could spend thousands of dollars so easily on clothes, shoes and accessories. This was how she later met John F. Kennedy Jr. He was a client of Calvin Klein and as one of the brand’s VIP clients, Carolyn quickly became familiar with him through fittings. After dating on and off, she officially married in September 1996 in a private wedding.
In old images of Carolyn, you can see how she captured a minimalistic style that is still iconic today. There’s much to know about how you can also capture a style similar to Carolyn’s so let’s dive in.
Minimalism matters
In many outfits that Carolyn would wear, you can see simple colors like black, white, beige, blue jeans, black t-shirts and a headband. She gave this chic appearance while not doing much on her outfit which is always great because sometimes more doesn’t look as appealing. You can experiment with your own closet but try to put together clean, neutral colors and not too many designs or logos. Build a wardrobe of versatile pieces that can all be styled effortlessly together.
Invest in quality basics
Just like Jackie’s outfits, Carolyn also went for timeless basic pieces and you can do the same by investing in high quality ones. As mentioned before, Carolyn often wore straight leg jeans, crisp white shirts, turtlenecks, small oval sunglasses, suede, blazers and more. Focus on these high-quality basics that will last in your closet rather than the trendy pieces that will not last after a few washes.
Opt for subtly and being less flashy
Less is always more so try to go for this approach when you don’t know how to style a certain look. Carolyn went for minimal accessories such as a structured handbag, simple gold jewelry, sunglasses and not a lot of trends. This can enhance your look without overpowering it because you’re going for the less is more approach. You’re not overdoing it on logos or brand names.
Go for monochrome looks
When in doubt, monochrome it out. An outfit in one color can never do you wrong and it is such a simple way to go for an elevated look without doing too much. Monochrome outfits are something else Carolyn always went for such as an all black look with a headband and a simple bag. These are so easy to achieve and do without breaking the bank.
Where to Shop for Outfits
If you’re looking to focus on high-quality basics, timeless pieces and versatile looks for your closet, we’ve rounded up some options that you can go to for capturing this style of fashion.
- Ralph Lauren
- Ann Taylor
- J. Crew
- Uniqlo
- The Row
- Cos
- Nordstrom
- Everlane
- Theory
- Celine
- Mejuri
Glamour & Guide 