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Reese Witherspoon’s an unlikely architect, but—to some degree—that’s exactly what she’s doing these days. Over the past six years, the actress has been expanding her sphere, launching a production company, a series of clothing and accessories boutiques known as Draper James, a video-on-demand channel with AT&T, and now, a lifestyle book, Whiskey In A Teacup. She’s building her own world. Though, to hear her describe her empire in the making, it’s less about being the next Oprah or Martha Stewart or Gwyneth Paltrow—it’s more about finding something that’s so indelibly part of her that she can’t shake it. It’s how she lands on any idea worth pursuing.
“I have to be haunted by it,” she says. “I have to talk about it again and again, and that’s when I know it’s a good idea.” Her sense of purpose has to outweigh the fear she feels in plunging forward, even if it’s something she’s never done before, like well, any of the aforementioned projects.
It’s the night before her book tour officially launches, and she’s sitting on the second floor of Crate and Barrel’s SoHo store, sitting on a panel alongside the company’s CEO, Neela Montgomery, Poshmark co-founder Tracy Sun, and moderator Elaine Welteroth. Her hair’s in perfect loose waves; her navy, Draper James dress totally wrinkle-free; nothing about her seems like someone who lives with a constant undercurrent of fear thrumming in the background as she plans her next move. And yet, to hear her tell the group of about 40, a certain degree of uncertainty is part of her day-to-day routine.
“If you’re not a little bit scared, you’re probably not living,” she asserts, matter-of-factly.
As surprising as the disconnect may be—Elle Woods, afraid?—it makes sense when you consider the inspiration behind the title of her lifestyle book, Whiskey In A Teacup. It’s a phrase she borrowed from her grandmother, Dorothea Draper—the “Draper” in Draper James—who believed southern women embodied beauty and strength.
“We may be delicate and ornamental on the outside, she said, but inside we’re strong and fiery,” Reese writes in the book’s intro. Like a stiff drink served in fine china, her potency is completely underestimated, and that’s just part of Reese’s allure.
“If you’re not a little bit scared, you’re probably not living.”
It’d be all too easy to dismiss her as another actress stamping her name on new brand extensions in an effort to rake in more cash—you know, beyond her estimated $198 million career earnings—or extend her relevancy beyond the box office. But that’d suggest a lack of involvement, and if you think Reese isn’t entirely in control of the life she’s building, you’re dead wrong.
Reese Is Marketing A Way Of Life.
She’s creating something that transcends the multi-hyphenate celebrity stereotype. She’s building a superbrand, launching herself into an echelon of multifaceted entrepreneurs that few stars have transitioned to. If Oprah’s about living your best life, Gwyneth’s living your most luxe life, and Martha’s about helping you perfect your life, Reese is more about uncovering the story within your own life, rooted in your history (in her case, growing up in the South) and shaped by your experiences. With her guide to Southern life—and by making the face of her Crate and Barrel line Draper James, not her, specifically—Reese is building something beyond herself. She’s creating a community.
In a way, it’s like she’s subconsciously taking a page from traditional neighborhood development: building a mix of different types of housing, all focused around a town center. The mediums she uses to spread her message—you can watch her on TV, see her (or the movies she’s producing) in theaters, read her monthly book club picks, or visit her stores—are the homes. The persona she’s become known for (a poised woman with a tough-as-nails core) is the town center people flock to, eager to identify similarly.
It’s only fitting that her nine-city book tour launched at a venue called Town Hall in New York City; these events are from your typical signing. Here, people pay $59 or more to fill a theater to spend a night in Reese’s orbit, hearing her tell stories about how growing up in the South shaped who she is today. The chance to meet her will set you back at least $350, depending on the venue, and many locations feature a surprise guest, be it comedian Ali Wentworth or singer Sheryl Crow.
“Easy doesn’t change the trajectory of your life.”
In a sense, you’re getting the lay of the land, straight from the mayor herself. When you leave, you’re handed a copy of the town’s bylaws to take home (AKA a hot-off-the-presses copy of Whiskey In A Teacup). Recipes intersperse chapters on how Reese decorates—imagine a healthy dose of wicker, wallpaper, and monograms—plans dinner parties, and gets her “do-gooding” on, all tying back to the importance of connecting with people.
It’s even more fitting that one of Reese’s big focuses is her monthly book club picks. Her trajectory actually dovetails with the three C’s Harvard Business school professor Ryan Raffaelli cites for the resurgence of independent bookstores in recent years: community, curation, convening. Reese’s Book Club is a prime example of this, but so is her production company, as the star curates women’s stories (like A White Lie, about the first black woman to attend Vassar College) to share them with the masses.
She’s Created A Starbucks-Esque “Third Place.”
Since Reese launched Draper James in 2013, the brand’s expanded to four retail stores, which serve as physical gathering spots, reinforcing that sense of community. As soon as you walk in, you’re offered a cup fo sweet tea—a classic show of Southern hospitality—and you’ll notice all the tufted sofas, wicker chairs, and stools inviting you to hang out and stay a while. The shops regularly host book signings and other events too, all welcoming you into the lifestyle that’s piqued people’s interest since Reese became a household name in the late ’90s, hitting a tipping point shortly after Legally Blonde and Sweet Home Alabama.
It’s no wonder that some 17 years later, people are still begging for a Legally Blonde 3. While that’s reportedly in the works, Reese has already crafted a more authentic version IRL, and this is a world everyone can live in. One that revolts against the idea that being feminine means being weak, that relishes in nostalgia just as much as it looks forward, and yes, really, really loves to monogram anything that isn’t moving.
It’s a sense of belonging rooted in the message that yes, life is messy and heartbreaking, but it’s also beautiful, and the only thing you really have to do to enjoy it—to live la vida Reese, or rather, Draper James—is show up for it.
“Easy doesn’t change the trajectory of your life,” she says during the panel, later landing on a statement that’s an equally critical part of her ethos: “Do what you say you’re going to do. A huge part of being successful is reliability.”
Now that’s something to embroider on a pillow. Or make your town motto.
