Carolyn Bessette Kennedy was ‘irked’ by ‘little miss perfect’ Gwyneth Paltrow

I have such strong memories of a Chloe Sevigny interview in Harper’s Bazaar, circa 2001, where she called out several celebrities including Gwyneth Paltrow. Chloe praised the late Carolyn Bessette Kennedy for being fashion-forward and then Chloe said something like “Gwyneth wishes.” There was a period of time in the 1990s when Carolyn and Gwyneth were two of the most famous women in America, and they wore similar styles for a time. To be fair, many women were doing that minimalist-chic/American-classic look. To be fair, Carolyn was considered a major style icon in her day, and many women were copying her in real time. I’ve always believed that Gwyneth was one of Carolyn’s biggest imitators, and Chloe Sevigny felt the same way! Well, as it turns out, Gwyneth and Carolyn met a few times through Carolyn’s job at Calvin Klein. Carolyn couldn’t stand Gwyneth, at least according to this new Gwyneth biography.

In the mid-90s, Gwyneth Paltrow and a not-yet-married Carolyn Bessette were both blonde, beautiful, privileged and fashionable young women raised in or around NYC who would dominate national headlines — but they decidedly were not friends. In Gwyneth: The Biography, author Amy Odell reports that the fellow It Girls had a professional connection via Calvin Klein, where the future Mrs. Kennedy served as a publicist and Paltrow was a celebrity client. As revealed in an early book excerpt exclusive to Us Weekly, Se7en star Paltrow “irked” Bessette:

Gwyneth said she had arranged for an appointment at Calvin Klein, where she had become a regular presence at the office. One of the publicists on the brand’s small team who helped Gwyneth was Carolyn Bessette (who would go on to become Carolyn Bessette-Kennedy). According to one person familiar with her thinking, Gwyneth irked her. When there were pictures of Gwyneth in the papers, Bessette, who viewed her as “little miss perfect,” would make cutting remarks about her.

With or without Bessette’s begrudging help, Paltrow was enthusiastically championed and dressed by Calvin Klein since the earliest days of her fame; he threw parties in her honor and lent her his helicopter, while she sat in the front row of his fashion shows around the world. Paltrow wanted to wear the brand in her 1998 film Sliding Doors, although its expensive, high-end line was mostly “too fabulous” for her role as a British woman who works at a sandwich shop, Odell writes.

How does Paltrow feel about the bombshell book? The mogul, 52, “isn’t too bothered,” an insider told Us exclusively, adding that she’s “been in the Hollywood game for a long time and so has a thick skin. This book isn’t a big deal for her.” Unlike Odell’s last A-list subject — none other than Anna Wintour, for 2022’s New York Times bestseller Anna: The Biography — Paltrow “did not participate” in the process, the insider said.

[From Us Weekly]

Do you believe Carolyn made snotty remarks about Gwyneth? Sure. I believe that. Just like I believe that as soon as Carolyn was John Jr’s established girlfriend/fiancee/wife, Gwyneth basically copied Carolyn’s whole look, down to her shade of blonde. Even in the 2000s, you could see Gwyneth still doing a version of Carolyn Bessette.


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Photos courtesy of Cover Images.

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46 Responses to “Carolyn Bessette Kennedy was ‘irked’ by ‘little miss perfect’ Gwyneth Paltrow”

  1. Blogger says:

    Carolyn’s dead and this is the first time I’ve read of her being snarky towards Gwyneth. Why would she given her professional role?

    Carolyn is like a Sphinx at this stage and all these quotes attributed to dead people can’t be refuted so I take these with a grain of salt.

    Unless she wrote “I hate Miss Perfect Paltrow”, I’d think she had more on her plate than muse about Gwyneth.

    • Megan says:

      Who is the audience for this book? If this is the juiciest gossip it must be a real snore.

    • Duch says:

      Except it does seem reasonable since I think that Carolyn Bessette didn’t have a nice thing to say about anyone. All the comments I’d read from her is how so-and-so didn’t live up to her standards.

      I think she was never in a good place, never got the chance to settle into her life and be happy/content.

      • Deering24 says:

        🙄🙄🙄 Yeesh. What’s that quote about the poor are under the burden of work…but the rich put themselves under the tyranny of (trifling) rules? What an awful way to live…

  2. Jan says:

    Carolyn and Gwyneth were not much different from one another, except I don’t remember Gwyneth having a cocaine problem, or being in screaming matches with her boyfriend/husband.

    • Jegede says:

      Exactly what I said.

      Carolyn was also -like Gwyneth – VERY image conscious of what her friends looked like.

      According to Terenzio, Carolyn had no problem – lovingly of course🙄🙄- telling them when their weight was unacceptable to her.

    • Nikki says:

      Carolyn Bessette wasn’t raised in privilege like Gwyneth. The neighborhood she grew up in gentrified a lot subsequently, but her family was middle class: both her parents worked, and she worked at Target as a teen. JFK’s cousin Anthony and JFK laughed together about both marrying “Target girls!” , and Carolyn Kennedy was very unhappy her brother chose someone from such a different background. Carolyn was a self made success, and had amazing style, truly individualistic.

      • Em says:

        I mean, Carolyn certainly didn’t grow up mega-wealthy like Gwyneth. She wasn’t a nepo-baby surrounded by celebrities. That said, she grew up very comfortably in Greenwich, Connecticut (very posh area) in a nice house. Her mom was a school administrator and her step-dad was a surgeon. They were obviously upper-middle class. Normal civilians, for sure, but still not your average middle-class American.

        They were both privileged – but to very different degrees.

        But yes, I agree that Carolyn was absolutely a self-made success (unlike Gwyneth).

    • Sue says:

      Yep. We all have our problems. Carolyn tragically died when she was young and beautiful, so she gets sanctified a lot, I think. If the same horrible thing had happened to Gwyneth instead, we’d probably see the same thing for her.

  3. ThatGirlThere says:

    I do believe she called her ‘little miss perfect’ I appreciate Carolyn even more for it may she rest in peace.

  4. Thinking says:

    Irked like the rest of us? Like the same snark the rest of us say about Gwyneth?

    How is this the first time this story has come out? And why is every story designed to make everyone else look jealous of her? Brad, Winona, and NOW Carolyn? The first two I can sort of believe some jealousy transpired. Carolyn, I’m not sure.

    I feel Bessette was too worried about her privacy being invaded and, possibly Darryl Hannah, than thinking about Gwyneth.

    So Carolyn said something about Gwyneth but never anything about Darryl Hannah?? This is weird.

    If Carolyn said some snarky things I guess I can’t judge since, uh-oh, I’ve done the same thing.

  5. Chaine says:

    Why does that caption say “Brad Pitt lookalike?” He looks nothing like Brad and in fact I swear that’s Scott Speedman!

  6. Lens says:

    I am less snarky than the average about Gwyneth. She never irked me that much until yesterday when although I don’t follow her she was on my instagram feed asking what it is her husband liked about her and then reading his answer. Oh boy. I’m trying to think of what it would be like to have a husband who absolutely lavished praise on me like that. It just irked me a little!

  7. KC says:

    I’m trying to imagine every vaguely snarky thing I’ve ever said about a customer, co-worker, boss, acquaintance, client, and any other person I came into contact with throughout my long working life and Jesus help me, I would not be able to prove or disprove any of it. Does it surprise me that CBK found Gwyneth Paltrow annoying in her role as a publicist for a brand? Not one bit. Am I surprised that apparently “little miss perfect” is the worst thing that was said about her between co-workers/friends. Absolutely. That seems like a hilariously mild insult.

    • Tuesday says:

      This is where I am. Carolyn didn’t have to hate her, or spend time thinking about her, or be some crazy unprofessional just because someone mentioned Gwyneth once and she rolled her eyes. We’re all just people and sometimes get annoyed at other people. No big deal.

    • orangeowl says:

      I agree! In any case, Carolyn’s style is and always will be iconic to me. She’s just stunning. Gwyenth’s look here is similar but I don’t recall ever thinking Gwyneth was copying her. I feel like they were in completely social circles, with CK being the only tie.

      • SueBarbri33 says:

        Yeah and….I mean, we all kind of looked like that back then. I know I did. As far as I’m concerned, the only difference is that Carolyn sort of was the perfected version of late-1990s NYC-style. She had a good eye for aesthetics and so did John. They were just a great looking couple. I saw an advertisement for an upcoming documentary on the two of them recently and they were really quite striking and very cool.

    • Tis True Tis True says:

      Ah, yes. Fashion, where everyone is unfailingly kind and polite and would never say anything mean about an actress or socialite. JFC, it’s known as one of the catty-est most backstabbing industries out there. Not to mention the drugs and eating disorders. Even if Carolyn was a better person than average for the place and time, which she seems to have been, imagining her as some benevolent angel is some serious retconning. She deserves (and deserved) better.

      Also there have been several books written about her. Can someone recommend a good one?

      • Ula1010 says:

        Regarding books about CBK, maybe start with Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy (although I wouldn’t describe her life as ‘captivating,’ ‘Captive’ is probably the better word). It’s the only book that centers Carolyn, written by someone who actually knew her pre-JFK, Jr. Its also on sale right now on kindle, fyi.

        I’ve also read the two books written by JFK, Jr’s, former assistant, RoseMarie Terenzio. One is about their relationship and the other is an oral history of JKF, Jr. I just finished the oral history and his friends do talk about Carolyn quite a bit. I’m a big fan of oral histories and I read the book very quickly.

  8. Mmmmhmmm says:

    That headband slicked-back bun or sometimes ponytail look – I remember the pain behind my ears at the end of the day – trying to recreate it. She was just so “fashion.” And, I’m happy to see how her style has held up over time. It’s quite something.

    • orangeowl says:

      It really is timeless. I don’t think young people now realize how absolutely trendsetting she was back in her time. I know her look took work but she managed to make it look effortless.

    • jais says:

      It really is something. Her style and photos have held up over time. It does feel timeless. And that’s sadly bc she passed so young. Gwyneth has moved on through the 2000’s and different style time periods even if she’s stayed pretty minimal. But those photos of Carolyn in NYC during that time period have held up. They’re still captivating to this day. Carolyn will forever be that girl, that IT girl, and part of that is bc she died too young. The red lipstick, the blonde hair, walking down the sidewalks of ny. There’s no comparison really. They were contemporaries and played in the same style pool and I can believe Gwyneth was inspired by her to some extent. Who wasn’t? I’m just vibing off of photographs and not touching the personalities of either woman. That’s a whole other discussion and not one I know enough about.

  9. Jegede says:

    Despite her image being sanctified post tragic death, the books I’ve read from Carole Radzwill & Rose-Marie Tenzino suggest CBK and Paltrow had very similar dispositions.

    So no, they probably won’t have got on.

  10. HillaryIsAlwaysRight says:

    Goop copies Carolyn’s style to this day.

  11. sevenblue says:

    I don’t get it? Both look like an ordinary white woman in New York. What is there to steal in terms of style? It is very annoying they are writing this kind of bitchy gossip about a dead woman who can’t refute it. Now, that ghoul Ryan Murphy is fictionalizing Carolyn’s story, so I am guessing we are gonna see more quotes from her than we got when she was alive.

    • Eurydice says:

      Same here. This was the Calvin Klein aesthetic at the time and basically a NY look. It was similar in Boston, except nobody would spend money on a tailor – if your sleeves or skirt were too long, so be it. But very different in other parts of the country – whenever I had to do business in Florida or Texas, I looked like a little black bird compared to giant peacocks.

      • TigerMcQueen says:

        This was my experience. The Calvin Klein minimalist look was so very NYC specific. My PR/Marketing gig in the 90s took me throughout the south and occasionally to the west coast and women did not follow that aesthetic.

    • Josephine says:

      I never understood it either. They are exceedingly thin, well-proportioned blondes who wear classic, tailored clothes in “rich white women” colors. (I remember distinctly disliking the headbands – I find them very childish.)

      Gwyenth’s style has remained the same over the years, so hard to believe that she was copying anyone. One look at her mom tells you exactly where she got her inspiration from, and she stuck with it.

  12. Kay says:

    I remember seeing this pic years ago and rolling my eyes at how much Gwyneth was trying to evoke Carolyn:

    https://www.gettyimages.com.au/detail/news-photo/ted-kennedy-gwyneth-paltrow-during-directors-guild-of-news-photo/105279324

  13. Thinking says:

    Carolyn was private whereas Gwyneth was a complete open book. That’s one large difference I see between the two women.

    They might have been similar in private (ie maybe a weight obsession?), but Carolyn never sought to inflict her opinions on the public. In that sense, it’s hard for me to say anything negative about her. She wasn’t actively trying to annoy the public with her private opinions ( which might have been controversial, but she never shared them). She was like Jackie O in that regard rather than Gwyneth.

    • Crystal says:

      Well Paltrow was and is in a profession where it’s required for you to promote yourself, and later on Gwyneth was also building her lifestyle brand which while pretentious was very successful. Carolyn was one of the behind-the-scenes people in fashion and had no interest in a public persona and it meant her marriage was difficult. That’s the difference.

      • Thinking says:

        Gwyneth is way more of an open book than other actors. She literally compared what having sex with Brad Pitt and Ben Affleck was like. Jessica Alba has a lifestyle brand too but I’ve never seen her compare sexual partners. Gwyneth has no filter. She’s considered classy but I don’t get it.

      • Crystal says:

        For someone of her level of fame and exposure she’s hardly the most indiscreet person ever. And her and Carolyn’s differences weren’t because Carolyn was morally better or something or more tasteful or classy (I hate when we do this about women in the public eye anyway). This discussion about Gwyneth being the worst is tired. She gives tidbits because she was a massive celebrity even while it’s not the same post-Internet (I love Jessica Alba but she was never as notorious as Gwyneth) and she gave lifestyle advice because that’s what her brand is, even if it’s silly at times.

      • Thinking says:

        I didn’t say Carolyn was morally better.

        Do I think she was less annoying from a public persona standpoint? Yes, most likely.

        Do I think she was authentically more stylish? Yes, most definitely.

        Gwyneth has projected herself as being the arbiter of class, which is the only reason I brought the word classy in. That’s how her profiles describe her, but I personally don’t understand the assessment. Do I think she’s the worst? No. But I do think she’s better than other people in Hollywood? Not really.

      • Crystal says:

        People and Gwyneth herself ran with the idea she was upper class because she *was*, and is.
        I don’t know what your definition of classy is so it depends on that.
        As far as being less annoying to people – back in the day as it became clear she didn’t want to cooperate for interviews, the press made sure a lot of people hated Carolyn too in much the same way people found Gwyneth annoying. The press even attacked her family for suing the Kennedy estate for wrongful death as they were absolutely entitled to do.
        But we should also remember really the main difference is Carolyn is dead and Gwyneth isn’t, so Gwyneth can speak for herself now if she chooses.

      • Thinking says:

        I don’t have much to say about this anymore haha. If you like Gwyneth and don’t find her annoying, that’s perfectly fine.

      • Crystal says:

        Yes, but that’s beside the point, which is that inventing some sort of “mysterious” vs “open book” personality difference to compare these two women that we don’t even know doesn’t make sense, given they both pursued specific directions in the limelight. But it does play into silly stereotypes about famous women. Anyway, that’s all.

  14. Bethy says:

    Gwen’s 52😮I was a kid in the nineties so I never cared about Gwen or Carolyn, still don’t but John John🤤

  15. Grant says:

    I can’t wait to read this book! I want to read that Anna Wintour biography too.

  16. L4Frimaire says:

    I remember that time period and still think Carolyn’s wedding dress is still so iconic. Also reminds me that Calvin Klein was such a hot brand back then. Not just jeans but his actual runway collection. He was so influential. Now it’s just there. Bessette-Kennedy’s style was so distinctive that seriously couldn’t imagine Paltrow competing with it. I just remember her and Brad getting the same haircut and color.

  17. Crystal says:

    Carolyn was known to have an acerbic sense of humor at times. But I would also venture some of this bitterness was because Gwyneth was always the media darling, and as Carolyn retreated more and more into wanting privacy after marrying John, the press turned on her and wrote the worst things. (People STILL think it was Carolyn’s fault the plane went down that night “because she was late getting a pedicure” – the press did that.) I can imagine Carolyn feeling some annoyance about the situation.

    • ThatGirlThere says:

      Okay, We get it. You love Gwyneth.

      • Crystal says:

        I actually don’t have that much of a problem with her and among adults this is not a controversial opinion, lol. And in feeling that way, I’m in good company given that Meghan herself spoke about how much she admired Gwyneth in her Tig days.
        My comment was also largely about CBK, so work on reading comprehension.

    • Jaded says:

      The press also tried to blame her sister Lauren for arriving late to the airport saying she was delayed due to a late business meeting in Manhattan. All pure bullshit. It was JFK Jr’s fault. He was not trained to fly at night under the low visibility conditions (marine fog, it’s deadly as my pilot husband knows well). He was only certified to fly under Visual Flight Rules (VFR) but did not have the instrument rating to fly solely by reference to instruments, especially in the dark over water.

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