Sophie Habboo: Motherhood, Made in Chelsea & Building Longevity

Sophie Habboo joins Bailey to talk about life after Made in Chelsea, becoming a mom, and building a career with staying power. She opens up about navigating self-doubt, finding her identity again after having a baby, balancing motherhood with ambition, and why women shouldn’t feel guilty for making…

Listener Q&A: Dating Apps, Making Friends & Feeling Lonely in Your 20s

In this solo Q&A, Bailey answers your questions about dating, friendships, and figuring out life in your 20s. She gets candid about why she hates dating apps, whether you should risk dating a friend, making friends as an adult, and how she handles loneliness while living alone and being single. Plu…

Emma DiMarco: Kissing Cowgirls, Brandy Melville & Building a Fashion Brand

Kissing Cowgirls founder Emma DeMarco joins Bailey Taylor to talk about building her fashion brand, finding her creative identity, and learning the realities of entrepreneurship along the way. Emma opens up about the expensive side of manufacturing, why she finally learned to hire people who know m…

Body Image, Ozempic Culture & Protecting Your Self-Esteem

In this solo episode, Bailey Taylor gets candid about body image, self-esteem, and the pressure to keep up in a world shaped by social media, fashion trends, and Ozempic culture. She opens up about her own weight loss journey, falling out of routines, and what it feels like to start over when your …

Mia Calabrese: NYC Dating, Red Flags & Why Ambitious Women Should Stop Settling

Mia Calabrese joins Bailey for a candid conversation about the realities of dating in New York City, why situationships have become so normalized and what she’s learned about dating more intentionally. They get into whether success makes dating harder for women, men who resent ambitious partners, s…

Claudia & Gabby: Co-Founding Vin., Good Taste & Building a Fashion Brand

Claudia Li Johnson and Gabby Kono-Abdi, co-founders of Vin, join Bailey to talk about turning their shared love of vintage and statement accessories into a fast-growing fashion brand. They share how their iconic Fishy bag came to life, why launching before everything was perfect worked in their fav…

Charlotte Palermino: Dieux Skin, Beauty Myths & Building a Brand That Lasts

Dieux Skin founder Charlotte Palermino joins Bailey Taylor to talk about building one of the most trusted skincare brands by leading with science, evidence, and transparency. She opens up about leaving the corporate world, why she wanted Dieux to be more than another trendy beauty brand, and how di…

Taylor Quitara: Art, Personal Style & the Power of Being a Little Weird

Artist and NYC cool girl Taylor Quitara joins Bailey to talk about building a creative life, developing your personal style and learning to embrace the things that make you different. Taylor shares how she turned painting into a career, used social media to get her work discovered and learned to tu…

Levi Sebree: Dating Without Rules, Friendship Green Flags & Breaking Into Fashion

Levi Sebree is back for a candid catch-up filled with dating confessions, friendship advice and the reality of building a career in fashion. She and Bailey compare New York and Los Angeles dating, debate underrated green flags and explain why the usual relationship rules rarely work. Levi also shar…

Listener Q&A: How to Build Confidence, Know Your Worth & Become Unstoppable

In this solo episode, Bailey answers listener questions about building confidence, recognizing your worth and becoming the version of yourself you want to be. She shares practical advice for moving past self-doubt, rebuilding your self-esteem and refusing to let insecurity keep you from opportuniti…