Finnegan Shepard of Both& Apparel - Fashion & Gender Joy

·28 min·2 clips

Finnegan tried on baggy Levi's hoping to become his breakdancing teacher, but saw only himself in ill-fitting pants.

This episode features Finnegan Shepard, founder and CEO of Both& Apparel, discussing fashion, gender identity, and entrepreneurship. Host Rocío Sánchez, a digital marketer specializing in queer business, explores how Shepard's personal journey shaped his brand for gender euphoric clothing. Shepard describes his early style as cycling through archetypes, like a breakdancing teacher's baggy Levi's, to express his gender identity. A pivotal moment came when trying on those pants revealed a fit issue, planting the seed for Both&. The brand focuses on solving specific fit problems, such as pants that accommodate both length and hip proportions, rather than promoting a vague "gender-free" aesthetic. Shepard argues the product resonates because it fills a genuine market gap for clothing that creates a specific, joyful silhouette. He states the brand's core belief is that many people want clothing that fits their body precisely to generate gender euphoria, not just baggier garments. As a startup founder, Shepard's biggest struggles involve balancing rapid growth with limited resources and navigating contradictory community expectations. He explains business values often conflict, like maintaining an accessible price point while offering extensive sizing or sustainable materials. Shepard finds it challenging when community critiques overlook the immense effort behind the scenes, especially given his personal investment. A key insight is Shepard's view that entrepreneurship lacks definitive formulas, with everyone in industries like finance and marketing "making it up" as they go. He emphasizes the importance of testing strategies and developing intuition rather than blindly following best practices. The conversation touches on fundraising challenges for underrepresented founders, noting they often receive less faith and support during market downturns compared to traditional founders. Shepard credits his resilience to a strong support system, including friends, family, and his partner, who provide crucial emotional and operational help. He concludes by explaining the brand's name embodies a "both/and" philosophy, opposing binary thinking in discourse and fashion. The episode's tone is conversational and reflective, blending personal narrative with practical business analysis. Listeners interested in queer entrepreneurship, ethical fashion, and startup challenges will find this episode compelling. Those seeking a purely technical business guide or disinterested in identity-focused branding might find it less engaging.

As heard by us

A queer fashion interview that links identity, integrity, and fit without losing its edge.

Transition of Style treats fashion as a way of talking about identity, commerce, and visibility. Rocio Sanchez and Finnegan Shepard, founder and CEO of Both And Apparel, keep the focus on what it means to build a gender euphoric wardrobe while staying honest about values, fit,…

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Why you'd press play

Queer fashion, gender euphoria, and a founder's take on fit, integrity, and style.

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