I didn't expect a television show to overhaul my closet. But that's exactly what happened when Love Story: John F. Kennedy Jr. & Carolyn Bessette dropped on Hulu back in February, and I fell down a very specific rabbit hole.
I came for the romance—that whirlwind, doomed, impossibly glamorous story of America's prince and the woman who never asked to be famous. But somewhere around the third episode, I stopped watching them and started watching her clothes.
Here's the thing about Carolyn Bessette: she wasn't doing much. A white button-down, slip dress. Trousers that fit. Black, black and more black. She looked like the most poised woman in any room she walked into. No logos, no trends, no trying too hard. Just confidence in the plainest possible pieces.
Then I looked at my own work wardrobe and felt a little deflated.
My clothes weren't bad; I've never been a bad-clothes person. I was voted best dressed in high school, and getting dressed has always been something I cared about. But here's what nobody warns you about: the wake-up-and-go-to-work routine will flatten anyone. If you're on autopilot every morning, even a good wardrobe starts running on defaults. I hadn't lost my taste—I'd just stopped using it. Watching Carolyn, I realized I'd let my work clothes settle into a rut, reaching for the same rotation instead of actually choosing the way I used to.
So, I did what any reasonable person does after being emotionally invested in a TV series: I made a list and went shopping (an investment, some might say). Here's what I took from her for the rest of us who have jobs and no connections to Calvin Klein.
Find the silhouettes you know work for you. Carolyn seemed to have maybe four shapes she really trusted, and she wore them over and over again. That wasn’t limiting. It just meant she knew what worked. I’m trying to get better about doing the same instead of convincing myself I need something completely different every time I shop.
Let black do the work. Wearing all black to work doesn’t look like you’re trying too hard. It looks like you already made up your mind. It’s probably the easiest way to make an outfit feel intentional because, let’s be honest, everyone looks good in black.
Stop chasing every trend. Carolyn’s outfits still look good thirty years later because she wasn’t constantly trying to wear whatever was new. Getting back into the habit of asking myself, “Will I still want to wear this in five years? Or even five months?” has talked me out of buying things that are trending in the moment.
Fit matters more than almost anything else. Nothing Carolyn wore looked expensive because it was flashy. It looked expensive because it fit her perfectly. I’m pretty particular about not buying or keeping things that don’t fit right. But looking back at her style reminded me why it matters so much. Fit is usually the difference between looking styled and just looking dressed. It’s not the most exciting thing to focus on, but it probably makes the biggest difference.
Carolyn’s style reminded me that getting dressed well doesn’t require more clothes, more trends or more effort. It requires knowing yourself well enough to make a decision and stick with it. In that way, it’s not all that different from a good financial plan: the goal isn’t to react to every new thing that comes along, but to make thoughtful choices you can feel confident in over time.
PYA Waltman (“PYA”) is an investment adviser registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training. More information about PYA’s investment advisory services can be found in its Form ADV Part 2 and/or Form CRS, which is available upon request. PYA-26-54