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What does getting dressed actually say about you? This week Eva and Caroline sit down with Jessie Freschl — entrepreneur, personal stylist, and founder of three businesses — for a conversation about fashion that keeps going somewhere deeper than anyone expected.

Jessie built her career working with women at every stage of life: new mothers whose bodies had shifted, professionals stepping into bigger roles, women who simply needed someone to be present with them in the most private room in their home. Her nonprofit Repurpose takes luxury excess and redirects it to students entering fashion and creative industries. Her newest company, Turnstile, is a tech platform helping women unlock the potential of the closets they already have.

And then there's the E. Jean Carroll story — given 48 hours notice, asked to dress Carroll for her trial against President Trump, and pulling from her own nonprofit's resale inventory because no designer labels were allowed in that courtroom.

The conversation covers the psychology of styling, mirror meditation, how bodies change from your twenties to your fifties and what clothes can do about it, conscious consumption versus fast fashion, and what it really means to let someone into your closet — which is almost always also letting them into your life.

Also covered: Golda Meir's Milwaukee roots, the movie Chef, sweatpants as surrender, and what Eva ate before recording that everyone immediately noticed.

Unfiltered. Unafraid. Unexpert. New episodes every Thursday.

@micdandmedicated | micdandmedicated.com

SHOWNOTES:

https://www.jessiefreschl.com/

Janelle Monáe Yoga

MY LIFE

https://www.amazon.com/My-Life-Golda-Meir/dp/0440156564

CHEF

https://www.rottentomatoes.com/m/chef_2014

AS A JEW

https://www.amazon.com/As-Jew-Reclaiming-Story-Those/dp/0063374978

Psychology of Styling

https://open.substack.com/pub/freschtakes/p/the-psychology-of-styling?r=18lt3h&utm_campaign=post&utm_medium=email

We’re two New York City women talking candidly about the chaos of modern life, from relationships, parenting, working in and out of the home, to what it takes to stay semi-sane in a world that expects you to hold it all together and be #blessed.

We couldn’t find an honest and vulnerable conversation — so we started one! If you need a laugh, a cry, or just want to hear someone else admit their flaws and validate your crazy, you’re in the right place. Be ready to be… Unfiltered, Unafraid, and UnExpert.

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Surgeon General Warning Disclaimer: We are self-prescribed unexperts, so if you have any real questions or need real advice, please call your nearest doctor.

© 2025 Eva Heyman & Caroline Leventhal