It’s nice seeing a young Carolyn Bessette in her high school yearbook, pre- John and before all the public attention she received, and being featured in gossip tabloids.
Her classic look, long full bouncy hair, light makeup and very natural.
It’s so lovely to see a young Carolyn Bessette looking genuinely happy, carefree, and at ease.
There’s something incredibly sweet about seeing a young Carolyn Bessette-this happy. The ease in her expression and the light in her eyes make the photo feel so full of life and warmth.
Calvin Klein was at the height of defining that clean, understated aesthetic his brand became famous for, and seeing him alongside Kelly Klein really captures the era’s polished, insider fashion circle. Add in supermodels like Christy Turlington and Kate Moss, and you’ve basically got a snapshot of the decade’s fashion elite.
The 90s Met Gala vibe was very different from today—less theatrical spectacle, more quiet power and influence. Calvin Klein’s circle, especially with those models, helped cement the “heroin chic” and minimalist look that dominated the decade.
If you look back at photos from that time, it’s striking how effortless everything feels compared to the highly conceptual looks we see at the Met Gala now. Do you prefer that understated 90s style, or the over-the-top modern era?
Kelly Klein, Christy Turlington, and Kate Moss weren’t just wearing beautiful gowns—they were essentially extending the runway into the Met Gala itself. Those custom pieces, often rooted in looks already shown in Calvin’s collections, embodied that signature 90s minimalism: clean lines, bias cuts, neutral tones, and almost no excess.
It’s also part of why those looks aged so well. Unlike many era-specific trends, Calvin Klein’s approach was about restraint and precision, so seeing the same designs move from runway to red carpet didn’t feel repetitive—it reinforced a cohesive vision.
Which era of the Met Gala is your favorite?
An excerpt from Michael Bergin’s memoir: The Other Man
Michael: One fine morning, at her place, we woke up late and she had to rush off. So I stayed and slept for another hour, finally stumbling out of bed and puttering around the tiny kitchen, looking for the coffee filters.
I didn't find them, but I found something else under the kitchen sink.
It was a copy of People magazine, stashed out of sight.
John Jr. was on the cover; the Sexiest Man Alive. It was really bizarre.
The issue was almost five years old—it dated back to 1988—and she'd hidden it away.
What the hell was going on?
Questions:
Do you think it was a little odd for Carolyn to have a five year old “People’s Magazine” of John Jr., stashed under her sink?
Carolyn had her eye on John ever since she spent that one weekend in Seasong back in 1991. That’s when they spent time with Carole and Anthony and after that one weekend John went back to Daryl Hannah.
Then November 1993 John and Carolyn were pictured for the first time on the curb watching the nyc marathon.
Why would Carolyn think that John would one day introduce her to Jackie if she continued being the other woman in their “friend with benefits” situation? Maybe John thought the same..
How could John ever introduce Carolyn to his mother if he was in a relationship with Daryl (even though his mom may not have approved) ? This was not a good being pictured with another woman when he was dating Daryl for several years.
Jackie was still alive in 1993, what did she think about this woman “Carolyn” being pictured with John? Was this a good look for her Carolyn?
Did Michael even question Carolyn’s intentions as her always saying “John is just a friend and it’s nothing. He’s not my type.”
John Perry has three daughters and they grew very close to John and Carolyn over the years. Please read and comment below if you think Carolyn went a little too far with plucking Anna Barlow’s eyebrows who was thirteen years old at the time.
An excerpt from Anna Barlow, JFK JR: Oral Bio.
Anna Barlow:
When we were older she would take us to Bloomingdale's. I mean, it was just like totally stepping into this miraculous, beautiful New York experience that can't be more exciting as a thirteen-year-old girl. I remember we went to Kiehl's, and I was like, "I want to smell like you." And so she bought me her mixture. It was cucumber scent and something else.... I just loved it. I still sometimes get the cucumber scent from Kiehl's.
She was the first person to pluck my eyebrows. She was like, "Oh, honey, we are getting rid of this." But in a way that was so... If any other person did that, you might be like:
"Did I not look okay before?"
We went home with clothes, makeup. I mean, as a young girl living in Wyoming, you're like, "Did I just meet a fairy person?"
Questions:
Why did Carolyn continue to give people make-overs?
She did it with Michael Bergin by plucking out his eyebrows, losing a Levi’s gig. Years later she does it to a thirteen year old girl.
Why would Carolyn think it was okay for her to pluck a thirteen year olds eyebrows?
Would you allow your friend’s wife to pluck your daughter’s eyebrows just because she didn’t like the way her natural brows looked?
Did John Perry Barlow and his wife excuse the fact that she plucked out their daughter’s eyebrows because she was married to John?
For Anna Barlow being thirteen years old at the time, she questioned herself after Carolyn plucked her eyebrows, “Did I not look okay before?”
At this age any girl is questioning her look or identity..Questioning everything about herself especially what she thinks beauty is or looks like.