It Girl with Bailey Taylor

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 time for themselves. Sophie also shares what she’s learned about marriage, protecting her peace online, growing a media company with her husband Jamie, and why authenticity has been the key to bringing her audience along through every new chapter.
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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. Plus, Bailey talks post-grad life, the best part of being single, her dream date, leaving high school friendships behind, and why putting yourself out there can completely change your social life.
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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 more than she does, and the surreal moment she discovered Brandy Melville was selling clothing using her brand’s name and imagery. She also shares how community, pop-ups, and social media have helped shape Kissing Cowgirls and where she hopes to take the brand next.
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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 confidence is low. Bailey also shares her honest take on the return of ultra-skinny beauty standards, why she believes health and strength should be the goal, and how comparison online can distort your sense of reality. From small daily rituals to movement, skincare, mindset shifts, and learning to slow down, this episode is a raw conversation about taking your power back and building confidence in a healthier, more lasting way.
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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, splitting the bill and why you should never have to question whether someone actually likes you. Mia also shares one unforgettable Hinge date, helps Bailey officially block and delete an ex, and gives her take on everything from red flags to the classic “if he wanted to, he would.” Plus, she opens up about what she’s looking for in a partner now, her career goals and why her mom will always be her ultimate It Girl.
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