Carolyn Bessette-Kennedy is everywhere again but the conversation around her style often misses what actually made it so compelling in the first place.
I sit down with writer and repeat guest Larissa Mills to talk about the frenzy surrounding CBK right now, from the new Love Story series on FX and Hulu to the endless stream of content promising you can dress like her if you just buy the right boots, coat, or sunglasses. Together, we unpack what people are getting wrong about Carolyn’s style, and why it was never really just about the clothes.
In this conversation, we get into:
- The Carolyn Bessette-Kennedy style revival happening right now
- What people are getting wrong when they try to copy CBK’s look
- What it was actually like to live in New York during the Carolyn era
- Whether Carolyn was seen as a style icon in real time — or became one later
- Why her style felt powerful because of her aura, confidence, and restraint
- How social media and overconsumption have changed the way we approach personal style
- The difference between being inspired by someone’s wardrobe and replicating it
- Why repetition, discernment, and editing are the real keys to great personal style
- How to take inspiration from Carolyn’s wardrobe without losing your own point of view
- The brands, silhouettes, and styling tools we’d use to channel the spirit of CBK in a more personal way
Timestamps
05:00 CBK resurgence, Love Story and the social media frenzy
07:00 Why “dressing like Carolyn” misses the point of her style
09:00 Larissa Mills on personal style and impenetrable taste
10:00 What women were actually wearing in NYC during the CBK era
12:00 90s minimalism, Calvin Klein, and the “uniform” of the time
14:00 Was Carolyn a style icon in real time—or did that come later?
17:00 The role of aura, presence, and her relationship with JFK Jr.
20:00 Why CBK’s style felt powerful beyond just the clothes
23:00 The difference between copying vs. embodying personal style
26:00 Overconsumption, the internet, and losing individuality in fashion
29:00 How to build personal style through repetition and restraint
32:00 Tailoring, fit, and the reality of making clothes work for you
34:00 Heels vs. flats and the practicality of everyday dressing
36:00 Breaking fashion “rules” and wearing what you actually love
38:00 Editing your wardrobe and developing discernment
40:00 Signature pieces, silhouettes, and building a personal uniform
42:00 Why you’ll never be CBK and why that’s the point
43:00 Introducing “Let’s Get You Dressed” (listener styling segment)
Follow Larissa on Instagram https://www.instagram.com/larissamills/
Let’s Get Dressed
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Let's Get Dressed