Episode 37: designer and fashion executive Andrea Chynoweth

Andrea Chynoweth

This is a super-long one, but I just could not bring myself to make it shorter because I loved every minute of this conversation.

To make it easier to navigate, I have broken it down for you below. Listen to it beginning to end (which, you know, I totally recommend because it’s good), or pick and choose the topics that interest you most.

I highly recommend not missing the Vivienne Westwood section, as well as the yoga and trends parts, oh, and the part about what Andrea loves about this phase of our lives.

And if you’d like to watch to the video, please click here (or above).

Please let me know what you think!

Video and audio editing by Sofija Jovanov.

Jump to Key Topics

3:22: Girl in Transition + Timbuk2 9:30 A designer’s business sense and entrepreneurship

16:44 Chicago origins (she wasn’t always a fashion girl)

26:10 First fashion gig with the legendary Vivienne Westwood (and how she got it with a the craziest resume)

32:57 Being open and spontaneous and also a responsible adult

35:42 AGING and being an overgrown teenager and planning to live until 139 and dating younger men

46:45 Mentee and mentorship over the years

51:46 YOGA

1:00:33 TRENDS! Loved and hated

1:09:09 “Genderless fashion is the NOW of fashion”

1:16:28 What she loves about this phase of our lives (don’t miss this one!)

Key quotes

“I’ve never moved for a job.”

“Genderless fashion is the now of fashion.”

“Sometimes I look like a grown up woman, sometimes I look like a teenager, sometimes I look like a hight school skater boy.”

“The time has gone by when only certain people are allowed to have certain experiences.”


As Timbuk2 turns 30, its female executives are building a lifestyle powerhouse

Anti-aging ads are out

Podcast with Wini Linguvic my yoga instructor

The Spring/Summer 1993 Vivienne Westwood show with the last-minute dyed dress as the finale

Pharrell on the cover of Vanity Fair, November 2019

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