Home cover story Ali Wentworth

Ali Wentworth

by devnym

By Chesley Turner
Photography: Spencer Heyfron

Ali Wentworth’s style is a confluence of easygoing casualness and underlying fearlessness, and the creative output that results is full of candid observation and curiosity.

“Yeah, I think it’s fearless. But I think that I know how to read the room. I’m not trying to be provocative…but I see things the way I see things.” Perhaps that skill for social finesse that just skirts the third rail is not quite as surprising when you consider that her mother was a Democrat who served as White House social secretary for the Reagan administration. It’s bred in her. But her creative work isn’t political; she’s just keeping an eye on things and giving us the benefit of her unique perspective.

“I think my humor and the way I observe things came from a reaction to growing up in Washington during Watergate, where I found everything to be incredibly tense and humorless. I thought politics were corruption…. I was going to school with G. Gordon Liddy’s son. So I think my creative, comedic mind came out as a reaction to all of that.” Maybe it was inevitable that despite ditching the capital to move LA for several years, Wentworth ended up back on the east coast, married to George Stephanopoulos, and offering her comedic take on the baffling times we’re navigating.

Roberto Coin Dress | Chiara Boni @chiarabonilapetiterobe | Jacket Iro @iroparis | Heels Alaia

In her recent book, “Ali’s Well That Ends Well: Tales of Desperation and a Little Inspiration,” Wentworth uses her signature voice to bring a little levity to surviving COVID and demystifying persistent taboos. “I don’t really understand why people don’t talk about things. I don’t know what that is. Growing up in my family, you know, we never talked about sex. So, because of that, as an adult, I talk about sex. Because it felt repressive and tight to me as a kid. So, again, it sounds like everything is a reaction to my childhood…. But everything is a reaction to my childhood.”

Her personal stories are only circumspect when her kids’ experiences are in the telling, whether she’s writing or podcasting or guest-hosting on LIVE with Kelly and Ryan. “Initially, when I was writing stories that I thought were completely innocuous and funny, you know, my children were like, ‘These are our stories. You can’t tell them; you can’t use them for humor.’ So, I stopped doing that. They’re allowed their privacy, and it’s their story.”

That personal perspective isn’t just meant to preach, but to connect. “I’m not a provocative person. I don’t say big sweeping extreme political stuff at all. I make, you know, I make jokes about myself.” Wentworth imagines the benefits of a more open, connected world. “Can you imagine if we were all just really honest with each other, and humanity was warm and inclusive…especially women.”

Top Maison Margiela | Skirt Stouls | Heels Tom Ford | Belt Vintage

For example, Wentworth remembers when she was considering blepharoplasty to eliminate the bags under her eyes. She called a bunch of friends and acquaintances in New York and LA looking for recommendations on plastic surgeons, and everyone denied ever having had any work done.

“They all denied it. ‘No, I haven’t done anything,’ and I thought, How!? I’m telling you I’m doing it! Don’t lie to me. I actually wrote a piece about it because I felt like I was trying to get an abortion in the 1950s, you know – or today, as it turns out. I didn’t understand why women wouldn’t reach out and try to help each other.” So, she offered up her own experience, videoing the prep, process, and recovery, so that other women could learn from her experience. “Why not be relatable to each other? It’s like, we don’t talk about menopause; let’s all pretend that we’re fitter and better and happier than we are. But I have found that when [I’m] with a group of women and I give myself, you know, I’m the sacrificial lamb; I say, ‘Hey, listen, marriage is hard, blah blah blah….’ And then everybody starts feeling comfortable.

“I think people should communicate. I mean, you know, women particularly. Women – we do have our own sort of oral history. When one of my kids was sick when they were little, I wouldn’t call my doctor. I would call one of my girlfriends. Women have the knowledge that we hand to each other all the time. I think if we have uncomfortable conversations, it helps us all.”

Pants KZ K Studio | Heels Manolo Blahnik | All Jewelry Roberto Coin

In a social-media-oriented world, however, Wentworth acknowledges the benefit in never having been an ingenue, overly reliant on perfect looks or tying self-worth to outward appearances. “For me, now, sexy-sexy is over, you know. I’m happy to put on a straw hat and grow tomatoes.” Still, for young women and girls, there is much to navigate. “I can’t imagine being a teenager in this world. I joke, but I’m like, they’re teenagers! They’re supposed to be out holding up liquor stores and getting pregnant.” Somewhere amidst the pandemic, the Trump years, the politics, the climate crisis, the overturning of Roe versus Wade, our kids are trying to grow up, learn who they are, and learn who they want to be. Their attempting self-discovery in a world that seems out to get them. “If I were a teenage girl, I’d never get out of bed!”

As a mother of two young women, Wentworth admits: being a parent right now is harder than ever before. You’re worried for your kids, also anxious and sad and scared yourself. “I do find myself saying to the next generation, you know, you’ve got a shitload on your plate. We dropped the ball. And yes, we dumped it on you, and I hope that you – particularly my daughters – are fearless females that are going to go and do what they can to, you know, mop up our mess.”

It’s a different world, and today’s teens do have the strong benefit of more teenage role models. From Greta Thunberg to the survivors of the Parkland shooting, it’s okay to be an activist. “And they need to be, because the adults aren’t doing anything.”

When she has questions, Wentworth uses her podcast called, “Go Ask Ali,” to find the right people who can shed some light on the topic at hand. “I ask anybody that is an expert in something I’m interested in that I think a lot of other people would be interested in hearing about.” Season one was about how to raise a teenager in a pandemic, “because that’s all I was thinking about. I was talking to family therapists and anxiety specialists and Peggy Orenstein about sexuality and girls and how the pandemic sort of halted all that. And I talked to somebody that dealt with addiction and teens. All within the lens of being in a pandemic.” With season two under her belt and just starting season three, she still doesn’t have a specific hook. It’s just things she wants to know more about, where she isn’t the expert at all. “I don’t pretend to know more than I do.” Wentworth jokes. “I mean, my fashion podcast would last one second. I’d be like, ‘Wear jeans.’”

With her podcast, books, and a possible scripted series in the hopper, Wentworth has a packed to-create list, but home base is still her own house. With one daughter in college and the other a senior in high school, things are about to get very quiet at home. “I’m very cognizant of the fact that I’m soon to be an empty nester, so I’m going to be all over my daughter all the time, and she’s gonna hate it. Besides that, I have all these conversations with George about, you know, what the back nine of life looks like. I think we both are at a point where we want a little bit more quiet, a little more coziness. I feel cozier times ahead, which I’m looking forward to.” Still, she has no plans to slow her creative work, and sharing her creativity and curiosity with the world.

“I won’t stop! I promise.

Styling: Cannon @Thecannonmediagroup
hair: li murillo @lilovesyou
makeup: Meredith Baraf @meredithbaraf

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