“She’s an icon, she’s a legend and she is the moment” is the viral social media sound bite that is playing on a loop in my head as I watch Brooke Shields crush this issue’s cover shoot. Having modelled since she was 11 months old, Shields knows her angles and how to strike a pose better than most. She can also stare down the lens of a camera in a way that could melt celluloid. But as this magazine goes to press, Shields finds herself facing perhaps the biggest and most personal role of her life – that of an empty nester. 

Her youngest daughter Grier is joining her older sister Rowan this month at Wake Forest University, which means Shields is grappling with one of life’s most terrifying yet exhilarating questions “What’s next?” Not surprisingly, for those who know Shields, or have followed her close-to-six-decade career, it’s a question that the actress, model, author and businesswoman is addressing head-on. “I think this is the period of time in my life where almost everything I am doing is pretty much outside my wheelhouse,” admits Shields. “But you know, it’s ok if you’re uncomfortable, I would rather be uncomfortable, but still growing and learning and contributing.”  

For those who didn’t live it, it is hard to express just how ever-present and impactful Shields was on the collective cultural psyche in the late ’70s, ’80s and early ’90s. Perhaps if you wrapped the fame of all the Kardashian/ Jenner kids together you might just about grasp the enormity of her reach.  She was the wholesome it-girl next door who somehow seemed unaware of just how stunning she was. She starred in some of the era’s most memorable, and controversial, films – Louis Malle’s Pretty Baby, The Blue Lagoon and Endless Love. She also, at the tender age of 15, pretty much single-handedly made Calvin Klein jeans cool with a series of suggestive advertisements with the now infamous tagline that  “nothing” came between Shields and her Calvins. 

Recently that time in her life was laid bare in a frank and revealing two-part documentary, Pretty Baby: Brooke Shields, that debuted last year. It spans her career and delves into, among other things, the idea of exploitation. Something that Shields, who was managed by her mother Teri Shields, says she never felt growing up but can understand – especially after conversations with her daughters – why other people might. And as much as her own mother-daughter relationship was fraught, a topic beautifully explored in Shield’s memoir There Was A Little Girl: The Real Story of My Mother and Me, the actress hopes that some of her mother’s core traits have trickled down to her two daughters as they now make their way out into the world.

“Things like her sense of right and wrong, and truth and humour,” says Shields. “Also she had such a strong work ethic. Understanding that your time is not more valuable than anyone else’s. That you do not deserve to have any type of superiority or attitude, because right behind you there’s always someone willing to work harder. You just do it all to the best of your ability, and you don’t make anything about yourself. You watch and learn.” 

Shields and her daughters have always had a very close-knit relationship and the actress has enjoyed sharing new aspects of her life with her now young adult children. One thing she particularly delights in is seeing them dive into her vintage pieces and make them their own. Rowan pulled out the fire engine red dress that her mum wore to the 1998 Golden Globes and donned it for her prom. While, more recently, Grier took it up a notch and transformed her mother’s wedding dress, from her first marriage to tennis legend Andre Agassi to her high school graduation. Grier, who just made her catwalk debut at the Tommy Hilfiger show during New York Fashion Week, had the dress tailored and updated for the occasion.

“I was just thinking, wow, this is an interesting rite of passage for me,” remembers Shields of the moment her daughter asked to repurpose her wedding dress. “I almost feel like somehow she wanted to claim it, and by doing so, making it as if there was no man in my life before her dad. She made the dress her own, and I love it.” 

Without a doubt, Shields is very much living in the moment these days. With her youngest daughter’s imminent departure (when we spoke), there is a sense that she is stripping off the weight of the past to embrace a new and exciting chapter in her life. In some cases, she is quite literally doing this. Next month, she will be putting up for auction her personal pair of Calvin Klein jeans that she wore in the brand’s ’80s advertising campaign, as well as her The Blue Lagoon script and her high school cheerleading sweater. “My mom was so attached to everything, and I have been so burdened by stuff, it just gives me agita, and I don’t want it. I want this period to be like a shedding of all that baggage,” says the model about her choice to start cleaning out her closet. 

But Shields is also aware, from a cultural standpoint, of what her archives would be able to telegraph about the eras that she so very much embodies. To that end, she has had everything digitised for posterity. “Maybe after I’m gone this will make for an interesting analysis of a culture and of my life,” she says with a little shrug. 

Listening to the actress it is as if something has shaken loose for Shields in this past year. Besides launching her own company she also returned to acting with a lead role in the popular Netflix romantic-comedy Mother of the Bride. She stars as the lead love interest across from Benjamin Bratt. “Honestly kissing him was one of the peaks of my entire career,” laughs the actress. In the film, she gets to flex her underappreciated slapstick skills that haven’t come out to play much since her memorable guest star turn on Friends and her ’90s sitcom Suddenly Susan. 

It was a project that the actress relished and she looks forward to the next time she can sign on for another comedy, “it’s just like a shot in the arm for me,” she admits. But no matter how well the film did on the streaming channel, Shields is clear-eyed that at this point in her career, she will continue to need to create her own opportunities in Hollywood. “Now is the time to figure out what all this has been for. I can’t just sit around waiting for something to happen. I now know I have to be much more proactive in my life. I have to create the opportunities I want,” affirms the actress.

Another thing that Shields admits she is letting go of (at least a little bit) is her deeply ingrained people-pleaser personality. It’s a development that has come in particularly handy with her new role as the president of the Actors’ Equity Association, which is a labour union in the United States that represents people who work in live theatrical performances. It is a job the actress takes very seriously, as she considers the time she worked on Broadway, headlining in shows like Chicago, Grease, Cabaret, Wonderful Town and The Addams Family, as some of the most demanding and visceral thrilling in her career. “Theatre is the hardest job in entertainment. It’s emotionally, mentally, and physically exhausting, but it’s also the most rewarding because it can’t be taken away from you,” she affirms.

Shields hopes to use a bit of her celebrity star power to help generate some awareness and improve the lives of Broadway performers, but dealing with the politics of the role is forcing the actress to step out of her comfort zone. “I see now that I don’t have to have everybody like me. That is a revelation,” shares Shields. “I’m a people-pleaser at heart, and I want everything to be copacetic, but sometimes I have to say, ‘I’m sorry you disagree, but this is what has been decided.’’’

That sort of determination, and let’s be honest a fair bit of frustration, is also what sparked the author’s choice to write a third book. This one with a title that says it all, Brooke Shields Is Not Allowed to Get Old, which will drop in January. The title comes directly from the words that spilt out of a man’s mouth when he was introduced to Shields recently. “When he found out my actual age, 58 at the time, his whole demeanour changed. I thought to myself, ‘So you’re telling me if I’ve aged, that somehow means I have failed, that I’m a disappointment... that’s just ridiculous.”

That encounter snowballed into the book, which the author points out is the first book she has written while actually going through the subject matter she is covering. Just like with her online community, Shields hopes the book will be a conversation starter and open up dialogues about the issues that women over 40 face today. “We chase the fountain of youth, and all the while, we’re signalling to ourselves that right now, we’re not good enough. It’s so unfair, toxic, and unfortunately, the way our society is organised,” laments Shields. 

Brooke Shields Is Not Allowed to Get Old will pull together elements of scientific research and reporting, along with the author’s own first-hand insights and experiences regarding age-related bias. It’s designed to help inspire women as they face major crossroads and questions in their lives. “This is just where we are,” says Shields matter-of-factly. “We need to band together and feel good about ourselves, rather than feel like we’re worthless now that our kids are gone. It’s just so interesting because this messaging is out there in the zeitgeist, now in a different way, you’re seeing it pop up everywhere. And for the first time in my life, I’m neither ahead of the curve nor too far behind it, I’m actually riding this one.” 

Then, just before she hops off our call to go join her waiting family Brooke has one parting word of wisdom about life on the cusp of 60. ”This, to me, is an era of why not?” Why not indeed.

Photographer: Fernando Sippel
Stylist: Luca Falcioni
Cinematographer: Tom Ford
Production: We Made It
Executive Producer: Jorge Rose
Assistant Stylist: Stephani Jacobson
Make-up: Tiffany Patton
Hair: Sky Kim
Set Designer: Maisie Satler
Assistant Set Designer 1: Oliver Jaskowski 
Assistant Set Designer 2: Hoang Dinh
Gaffer: Peter Steininger
1st Acc: Tom Awender
Assistant Photographer: Juliana James 
Social Media Assistant: Mallory Brendel
Jewellery: Cartier