Tailoring Tradeoffs and Loving What You Wear

Larissa and Liv discuss tailoring decisions, heels versus flats, and accepting imperfect fits for beloved pieces.

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Episode notes

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