Jake Woolf is someone I’ve followed for a while on Instagram, so I was confident I was inviting a bird of a similar feather on the show. We both love to shop, explore, discover, and obsess over product.

We get into the weeds into the state of fashion, including trends, designers switching companies like pro athletes do teams, and we also talk about what he’d like to see more of in the near future. We later dive into the first of his several upcoming collaborations he has on the calendar for 2026, and you’ll get first dibs if you start subscribing to his Substack, one of my favorite corners of the internet.

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