One paradox of the Grateful Dead is that while the band was, and remains, vastly influential in matters of design and fashion, the members themselves tended to be...indifferent, at best.

The exception was Bob Weir, the sole Dead member who—for good and occasionally less good—seemed interested in forging a personal style, an interest that continues today in his collaborations with designer James Perse.

And who better to cast an evaluating eye on that style through the years than his two daughters: Monet, 21, who is an actor and a senior at Chapman University; and Chloe, 17, a high school senior in Marin County and budding filmmaker, who is joining her dad on the Dead & Company tour that kicks off this week to shoot film footage of the revivified scene.

Truth be told, we may have hoped for a bit more eye-rolling filial derision when the younger Weirs joined their father on the phone for a walk down his sartorial memory lane. They are notably kind and generous daughters. Still, they were not without opinions, as you’ll see as we take a Weir family outing through 50 years of Bobby Style.

September 15, 1967, Hollywood: Bob Weir relaxing during rehearsal at the Hollywood Bowl. Michael Ochs Archives

GQ: Okay, so, Weir Daughters, do we approve of this look?

Monet: Chloe is going to have a different answer than I am.

Chloe: Mo says I dress like a hippie.

Monet: She does! I respect that culture, but personally, maybe because I’m older and grew up around it more, I took a different route. I went more for normalcy.

GQ: Do you remember this day, Bob?

Bob: I remember it was hotter than the hinges of hell. We were on a bill with several other bands, and it was “the Sound of San Francisco” or something. I don’t remember who closed. Probably Jefferson Airplane. Anyway, it was our first time out on a big stage, and it was a big deal to us.