DREW BARRYMORE has spent 43 years charging forward. We asked her to go back to where she started.

One advantage Drew Barrymore has from living in the heart of the cultural consciousness for the past 35 years is that she has primo #TBT material. “When I was 6, my mom dressed me like a little 80-year-old woman,” Barrymore says, holding a stack of inspiration images on the set of her InStyle cover shoot. She lands on one from 1983 where she’s in a miniature black evening gown and pearls. “When I first unearthed this photo, I was like, ‘Are you kidding me? That’s my daughter Olive’s body 100 percent!’ ”

But it wasn’t only the trickle-down genetics and era-specific fashion that resonated. “None of those pictures were taken at home,” she says a few days later, sitting in the den of her Upper East Side apartment in N.Y.C. “Not like people would necessarily have pictures of me at home, but it’s almost like I never was at home. I was always out and about. That was the biggest takeaway for me.” She pauses and smiles. “And it’s funny because you’d have to take a crowbar and a spatula and a forklift to get me out of the house now.”

Barrymore’s apartment is equal measures Drew and her two daughters, Olive (5) and Frankie (3). Sandra Boynton books are stacked on Rizzoli monographs; Dr. Seuss mingles with Joan Didion. It’s cozy and personal—and has a super-impressive craft closet. It’s easy to see why the trio who inhabit the space would never want to leave. Tonight the family has just finished decorating two Christmas trees to a holiday playlist of Elvis Presley, Mariah Carey, and Bing Crosby classics. Miracle on 34th Street is on TV, soundless, in the background.

At 43, Barrymore is still finding room to explore. Outside of acting, which she still loves (her Netflix show, Santa Clarita Diet, returns for a second season this year), and producing (her company, Flower Films, has both TV shows and films in the works), the star also boasts Barry­more Wines by Carmel Road, the cosmetics line Flower Beauty, and Dear Drew, a clothing collection launched this fall with Amazon Fashion.

“I kept feeling this burning desire to build an apparel brand for women by women, to explore something romantic,” she says. “I took it back to my love of tailoring and having been in a costume house my whole life.” The cuts and silhouettes match Barrymore’s personal aesthetic. “I have a body type that I tend to cover up,” she says. “So it’s nothing tight, not big and boxy, more of a fluid drape that feels like the ’20s, ’40s, and ’70s. Not utterly casual but efforted in its effortlessness.

“I’m very conscious about the way people feel,” Barrymore says of how she looks at her growing empire. “When I was making movies, I just didn’t want to tell a depressing story; I wanted to tell one about some type of self-improvement. I thought, ‘There’s enough shit in life. I want optimism and joy.’ At the same time, I don’t like magic-wand happy endings—and now I don’t like magic-wand makeup or magic-wand clothes.”

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