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 opportunities, relationships or new experiences. Bailey also explains why confidence starts with your mindset, how small investments in yourself can change the way you feel, and why a little “delusional confidence” might be exactly what you need to stop overthinking and start going after the life you want.

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Iris Kendall joins Bailey Taylor for a dreamy conversation about life after Love Island, dating in your 20s, and finding your style era. She opens up about what really happens behind the scenes of reality TV, how the experience shaped her confidence, and the relationship lessons she’s taking with her now. Iris also gets into long distance love, money advice every woman should hear, building an authentic career online, and her boho chic approach to fashion — from French girl inspiration to the closet staples she’ll never give up.

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Violetta Komyshan joins Bailey Taylor to talk about the discipline, beauty, and reality of life as a ballerina. She opens up about growing up in New York, building a career in dance, and how ballet shaped her confidence, femininity, and effortless personal style. Violetta shares why color analysis changed the way she gets dressed, how she curates a more intentional closet, and why vintage ’90s fashion will always be a go-to. She also talks about protecting her privacy, choosing peace in her 30s, finding inspiration through fantasy books, and learning to build a life that feels more authentic, creative, and fully her own.

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Vintage Grace founder Chandler Guttersen joins Bailey to share the personal story behind the name of her beloved New York vintage destination. Chandler reveals how Grace—her first name and a tribute to both of her grandmothers—became the perfect reflection of the timeless, elegant, and welcoming brand she wanted to build. She also opens up about growing up on a Colorado cattle ranch, working at Gucci and Bottega Veneta, launching her business during the pandemic, and why true personal style will always matter more than following trends.

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Content creator and photographer Olivia Joan joins Bailey to talk about how sharing her grandmother’s extraordinary wardrobe online unexpectedly changed her life and career. She opens up about honoring that legacy while rediscovering her own personal style, embracing whimsical fashion, and learning to say no to opportunities that leave her feeling drained.

Olivia also shares what confidence looks like in her late 20s, why authenticity and kindness create lasting relevance, and how cooking, photography, and time away from social media help her feel grounded. Plus, she reveals her plans for a deeply personal coffee-table book and the quieter life she is building beyond the internet.

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Fashion writer and editor Leah Faye Cooper joins Bailey to talk about her journey from teaching high school in Houston to building a career in fashion journalism and landing at Vogue. She opens up about the years of rejection, freelancing, and ambition that shaped her path, plus why strong writing and thoughtful criticism still matter in an industry that has changed so much. Leah also shares how she defines great personal style, the importance of buying pieces you truly love, her passion for telling bigger cultural stories through fashion, and the ultimate It Girl who has inspired her most.

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In her first solo episode of It Girl, Bailey answers listener questions about breakups, situationships, dating again, and learning when it is finally time to walk away. She opens up about heartbreak, toxic relationships, chasing people who do not choose you back, and why healing does not always happen on anyone else’s timeline. Bailey also gets honest about being single, dating in New York, dealing with rejection, and finding the self-worth to stop settling for someone who makes you feel alone.

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Eva Meloche joins Bailey Taylor for her first podcast appearance to talk about growing up online, building boundaries with her audience, and learning how to keep parts of her life private while still sharing her world through YouTube. She opens up about finding her personal style through thrifting, Copenhagen fashion, and dressing for herself instead of chasing trends. Eva also talks about confidence, creativity, life in her 20s, her love of writing and Substack, and what’s next as she prepares for a new chapter in London.

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