The Evolution of Media: Insights from Willa Bennett

What's Contemporary Now?

Willa Bennett, a trailblazing force in media, is the editor-in-chief of Highsnobiety, steering the publication to new heights of innovation and influence. A Forbes 30 Under 30 luminary, her journey began at Seventeen, pioneering its queer vertical before igniting social strategies at GQ, and championing diversity as Condé Nast's global co-chair. The American Society of Magazine Editors recognized her for social media excellence and video programming, and her leadership at Highsnobiety garnered recognition in the Digiday and Muse Awards. Highlighting the importance of authentic narratives in connecting with young audiences, what she sees as contemporary now is pushing the boundaries and shaping the future of media—even if that means tuning out the background noise and tapping into real community.

Episode Highlights:

• Bennett grew up in LA, balancing two passions: masculine menswear magazines and hyper-feminine ballet practice.
• Talking about her early passion for vintage finds and retro styles, Bennett says experimenting with styling became another medium for her, “like writing.”
• She grew up reading publications like Teen Vogue, Seventeen, Nylon, and Dazed—publications she says understood young consumers and which she still keeps a few print copies.
• Bennett moved up through various roles in the industry at a time when social media marketing was in its more raw, early stage.
• Her role at Highsnobiety gives her creative freedom in that it moves with the youth culture and its fast-paced, creative, adaptive, and reactive workplace environment.
• Bennett is ahead of the curve, balancing personal perspective with editorial consideration and curation.
• Her team at Highsnobiety pushes a particular and intentional editorial vision, championing designers and talent that they want to carve out a space for.
• Some of Bennett’s favorite cover stars have been Billie Eilish, Andre 3000, and Pamela Anderson, though she felt strongly about the Dries Van Noten cover.
• Bennett has spoken about forming real connections as a priority over solely professional relationships, despite how “transactional” the industry can be.
• Under Bennett’s eye, Highsnobiety’s niche is to move in tandem with the zeitgeist instead of against it, never telling readers what to do or who to wear.
• Bennett considers real-life events crucial to foundational community building, saying, “that to me is a way bigger metric of success than like any influencer with 16 million followers posting one slide that everyone’s going to skip over anyway.”
• She’s published poetry collections benefitting The Audre Lorde Project for queer youth.
• For Bennett, deleting social media is what’s contemporary now, surprisingly.

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