The Timelessness of Carolyn Bessette Kennedy

If, like me, you are a Gen X / Xennial who grew up on a steady diet of Vogue and Vanity Fair, there is probably a not-insignificant folder in your mental Rolodex devoted to all things Carolyn Bessette Kennedy. There was a period of time, in the mid-to-late 90s, when CBK was the epitome of cool. But not, and I cannot emphasize this enough, Gone Girl’s Cool Girl:

“Men always say that as the defining compliment, don’t they? She’s a cool girl. Being the Cool Girl means I am a hot, brilliant, funny woman who adores football, poker, dirty jokes, and burping, who plays video games, drinks cheap beer, loves threesomes and anal sex, and jams hot dogs and hamburgers into her mouth like she’s hosting the world’s biggest culinary gang bang while somehow maintaining a size 2, because Cool Girls are above all hot. Hot and understanding. Cool Girls never get angry; they only smile in a chagrined, loving manner and let their men do whatever they want. Go ahead, shit on me, I don’t mind, I’m the Cool Girl.”

CBK would never, ok? At least, she never appeared like someone who would – drink cheap beer, play video games, burp. She did not visibly strive to be accessible, relatable, accommodating. She had the world’s most eligible bachelor running after her. I think she might have even made him cry once, in public. I don’t know about the male gaze, but mine, for one, was absolutely riveted by CBK.

I was reminded of this by a recent conversation with a friend, who told me that there are two different biographies of CBK currently in the works. I am cautiously excited by this news. I add that caveat because I have little interest in a conventional biography of the woman; what I am hoping for – what I have been waiting for, all these years – is a proper deep-dive into the mystique and mythology of CBK. Her public persona is an incredibly rich text, deserving of astute, fulsome analysis. Someone like Anne Helen Peterson might do it justice. Here, you’re stuck with me, giving it a college try.

An almost heretical thought struck me recently: CBK’s style was actually kind of boring. Wait, don’t start throwing stones at your screen just yet. Hear me out. Or, rather, allow me to show you.

Yes, she looks lovely. Elegant, chic. She really nailed that 90s clean-cut minimalism – was possibly at its vanguard. But try to separate the person (and persona) from these outfits. Cover her face, and just look at the clothes themselves. These are boring-ass outfits, be honest. If I wore any of these outfits to work tomorrow, I might get a compliment, but absolutely zero people would still be thinking about them 30 years later. I actually recreated one of her outfits a few months ago – because it had been stuck in my head for about 30 years, and I finally had the pieces to make it happen – and I was shocked by how “meh” I felt wearing it. It wasn’t a bad outfit; it was just unmemorable on me.

Yet, somehow, CBK remains a fashion icon to women of my generation – and, these days, is being discovered by younger generations too. There are still so many articles being churned out that aim to teach us how to “dress like CBK” and, honestly, I am starting to think they are missing the point. What fascinates us is the aura of CBK – or, rather, that of her public persona – and her clothes are not, on reflection, the source of that fascination. Clothes did not make CBK interesting; she made the clothes interesting. Copying her outfits does not allow the rest us to enter into the magic circle.

So what was it – the secret sauce? Was it something as simple as our culture’s fixation with WASP-y, thin, conventionally attractive, blonde women? I’m sure it didn’t hurt that CBK was all of those things, but she wasn’t a unique exemplar of that type; few of her cohorts have been able to carve out a similarly enduring niche in the cultural Zeitgeist. What set CBK apart? She was a public figure for a relatively short time yet has remained a potent cultural/style reference for decades afterwards. Why?

Perhaps it all comes down to silence.

CBK entered the public sphere in the pre-social media era. The internet was barely in its infancy. Sure, there were gossip magazines and celebrity culture, but the public did not have the same level of direct access to famous people that it does now. CBK was constantly in the media – especially in NYC – but she was written about. She did not speak. I’m not sure she ever gave interviews and, if she did, they were perfunctory ones – not the kind of soul-baring exercises (premeditated, yes, but crafted to achieve the impression of authentic connection) that have become the norm in the last 20 years. In her silence, CBK became a projection screen for the narratives that fascinated and compelled society then, and now. Was she a willing participant in this – indeed, a moving party in the whole process? Honestly, I have no idea. She certainly appeared to hate the media’s obsession with her and her personal life, but whether that perception was genuine or manufactured – or maybe a little bit of both – who knows? This is the deep dive I need someone smarter than me to do!

Thinking about all of this, I realized that CBK is not an exception. Society loves silent women – women who, for whatever reason, can’t or won’t to tell their stories in their own voice. Society loves women whose stories it gets to tell. Just look at Marilyn Monroe. OK, maybe “loves” is the wrong word. Just look at Marilyn Monroe. Let’s put it this way, then: society loves to consume women whose stories it gets to control. Beautiful women, especially. We will probably never know what CBK herself thought about the stories crafted out of her silence. She will remain forever just so: frozen in silence, frozen in time. Timeless.

What I Wore: August 2024, part one

Details: Max Studio top, Esprit belt, Ralph Lauren skirt, Old Navy shoes, Coach bag (all secondhand)

Thoughts: One of the favourite outfits of this summer, and I can say that with my full chest. I felt like a (prairie) princess in this outfit. Whenever I wear this skirt, I am always thankful that I decided to pull the trigger and splurge on it last year, because it brings me so much joy.

Details: Ralph Lauren shirt, Roughrider vest, vintage belt, J. Crew shoes (all secondhand), Ricki’s skirt (retail)

Thoughts: Wearing all white is tempting fate to the nth degree, but I did it. On a WFH day, because I don’t trust myself with this kind of outfit in public. I’m calling it a win because, not only did I NOT spill anything on myself, I looked pretty fab too (if I do say so myself). There is something so elegant about an all-white outfit paired with strategic accessories.

Details: Zara top, Icone shirt, UO skirt, Napoleoni shoes (all secondhand), Icone belt (retail)

Thoughts: I wanted to take this skirt in a Papa Ralph-approved direction, and make it summery at the same time. Plaid is more of a fall/winter pattern to me, so the top half of the outfit had a lot of work to do. I think the crop top + chambray combo managed to pull it off. I like how it’s the reverse of a typical lumberjack chic outfit — plaid on the bottom, denim on top. If I had worn this outside, I’d have gone with some cowboy boots for sure.

Details: Ralph Lauren shirt & sweater, Twik skirt, vintage belt (all secondhand), J. Crew shoes (retail)

Thoughts: I thought this outfit punched way above its effort level; it’s pretty basic, but it looks so sharp. I wore this on one of my rare office days … and I ended up being the only person there, which means nobody got to see this IRL. Sad. Well, at least you get to see it here.

Details: Sandro top, Lord & Taylor cardigan, UO pants, Saint Laurent belt (all secondhand)

Thoughts: This is the kind of very traditional outfit formula that I rarely wear these days — I have, like, 2 classic cardigans in my closet — but I made it feel exciting (to me) by adding an edgy metallic belt and a crop top that showed a tiny sliver of skin. Ooh la la! I have to say that the combination of magenta and black is also really nice and sharp; the two colours play off each other very well.

Details: Charlie Holiday dress, Roughriders vest, cowboy boots, Brixton hat, Lena Bernard necklace, Coach bag (all secondhand)

Thoughts: Simple summer style — maxi dress, vest, cowboy boots. I think I’ve been wearing cowboy boots almost as often as sandals this summer, which is an interesting turn of events for yours truly. But I’m leaning into this vibe, and enjoying the heck out of it. Turquoise and red accessories to finish off the fit; it’s a combination that never lets me down.

Details: Ardene top (retail), Silverado jacket, Cotton Pickers skirt, cowboy boots, Coach bag (all secondhand), Icone belt (retail)

Thoughts: I love this jacket so I take every cool-weather-day opportunity to wear it. I should branch out and try different colour combinations for it, but it’s hard to resist defaulting to white and blue. It looks so good! I’ve been debating whether this vintage skirt is special or unique enough to keep in my (crowded, so crowded) closet, but this outfit convinced me to give it another reprieve. Come fall, though, some tough decisions will need to be made. I am not looking forward to it, sigh.

Details: Chaps tee, Denim & Supply jacket, UO pants, vintage belt, Manolo Blahnik shoes (all secondhand)

Thoughts: Southwest-inspired, but make it business casual. I wore this to WFH, but I could easily bring it to the office. It’s a rather muted colour palette for me, but the sequins and metallic mesh belt add some visual interest. I don’t buy a lot of sequins these days, but I picked up this tee because I thought it was a nice, subdued way to do sparkle. Like, daytime sequins. It’s good to have some of those on hand. You never know when you might need to zhuzh up an outfit.

Details: Zara top, vintage skirt, Aldo shoes (all secondhand), Prairie Trail Goods jacket

Thoughts: Patchwork, doubled. The jacket and skirt are made for each other, aren’t they? I chose the platform loafers as a bit of a wildcard pairing, and strangely (or not, I did put some thought into it) I was very pleased with it. I like the juxtaposition; the vibe of the shoes adds a more contemporary edge to the outfit. And the colour is soooo versatile. These shoes were a solid addition to my closet — just like my brown and black pair.

Details: Liz Claiborne dress, Le Chateau belt, Barbara Barbieri shoes, Rebecca Minkoff bag (all secondhand), Bozzolo tee (retail)

Thoughts: When it doubt, rainbow dress it up. Literally. We had a brunch date with friends and I didn’t know / couldn’t decide what to wear, so at the last minute I pulled this dress out of the closet and — bam! Outfit done.

Details: NBA jacket, Calvin Klein tee, Everlane pants, Gap belt, Converse sneakers (all secondhand)

Thoughts: OK, so this jacket was a total random impulse buy at VV. I don’t care about basketball or the NBA (unlike my son, who is obsessed) but something about this jacket spoke to me. I like the cut, the quilted effect, the floral pattern, and — above all — the weird juxtaposition of it all. I wore this on a library outing with the kids, and I have to say: I felt like A Cool Mom all the way 😉

This is 44

The title speaks for itself. I am turning 44 today, which feels like a weird, random number. It shouldn’t, because, since January, I’ve been telling people who ask about my age that I’m turning 44, so I’ve had a while to get used to the idea. Maybe my age will feel weird every year from now on, as the number continues to grow, further diverging from my inner state of mind. It’s not so much that, in my mind, I feel younger every year (relative to my actual age); it’s that I grow more and more ageless. I hasten to emphasize that I am very much speaking of a mental state of being; my body is feeling every one of its actual years. It is nice, that: feeling ageless. It’s a kind of freedom. From the time I was a young adult until I entered my 40s, there were a lot of “shoulds” tied to every milestone. Graduate from university at this age. Find a partner by that age. Get married. Buy a house. Start a family. The clock always tick, tick, ticking. It’s a generational thing, I know — the boomers’ legacy that Gen X never quite managed to shrug off (or maybe didn’t try hard enough to do so). Now, on the other side of 40, I’ve either run out of “shoulds” or stopped giving a sh*t about them or both, because I find myself unshackled from expectations. The clock continues to tick, but it is a countdown of time to explore the world and my place in it. To go where my curiosity takes me, to live according to the dictates of my own heart. Age has very little to do with any of it.

I’m so thankful that I had the opportunity to have my portrait done by Emilie Iggiotti recently because it made me think about how I want and enjoy to show up to the world in this moment of my life. About the clothes that help me to that, and the role they play in my life. About the things I wear for myself, and the things I wear for others, and the slowly disappearing line between them. With every year that passes, I feel that I owe less deference to other people’s expectations of me. I am only at the beginning of my Crone Season. I look forward to its apotheosis; the outfits will be magnificent.

This is me, now.

I’ve always been self-conscious about my teeth, so I trained myself to never show them when I smile. Talk about censoring oneself in service of societal standards of beauty. I am so glad I trusted myself in this moment, and trusted Emilie to capture it as beautifully as she did; when I was showing my best friend the gallery of images from the shoot, she picked this one as being the one that best captured my inner light. I think she was right. It shows the joy that I rarely let other people (except those closest to me) see. Maybe this is the year I change that.

Why not 44?