'I like my age - I feel as alive, excited, and aware as ever': Anna Wintour's softer side emerges with rare glimpse of life beyond Vogue

With, arguably, one of the most famous hairstyles of all time, and an instantly recognisable look with her trademark sunglasses, it’s easy for many to feel like they know Anna Wintour.

However, despite being a fashion and cultural icon for decades, she’s notoriously one to eschew attention on herself and put the business of fashion, Vogue, and Conde Nast firmly in the spotlight. This is why her decision to grace the cover of Vogue alongside Meryl Streep is an exciting move.

While the two, naturally, discuss The Devil Wears Prada, Dame Anna offers a rare look into a different, more personal side of her, including her "relentless" attitude to parenting and how she feels about the "advantage" of getting older.

Interviewed in the magazine by Barbie director Greta Gerwig, Anna and Meryl, amongst much fashion and Miranda Priestly chat, get onto the subject of families. Both busy career women, they discuss the lessons they’ve taken from pursuing career excellence while being working mothers.

Anna shared, "Being a mother when you have the jobs that we have - you have to make the time. I was relentless about going to the games and turning up at the parent-teacher meetings, being there when it was important.

"I felt like Vogue could always wait and that it’s okay to be a busy mother. You make it work."

Anna has two children, Bee and Charles Shaffer, from her first marriage to David Shaffer. She was married a second time to Shelby Bryan between 2004 and 2020.

Today, as her family expands to include four grandchildren and four step-grandchildren, Anna values time together. "We love to celebrate birthdays and weddings; traditions are important - we’re English, so we constantly play games and stage countless tennis tournaments - and we try to take care of each other through thick and thin.

"I try to instil in my children and my grandchildren that it’s family that counts and family who will give you love and support. If you have that, everything else will be fine."

During the illuminating chat between three very distinguished women, the topic of age came up. And, despite working in an industry that has often been said to favour youth above all, Anna embraces being 76.

"I like my age. I feel as alive, excited, and aware as ever, and I like to learn from my children and from all my teams around the world. It’s always exciting."

"I think with experience, you have a sense of balance and proportion, and you know that life is not perfect and that things will go wrong and you’re just going to give it your best shot.

But if it doesn’t work, you have to move on. I feel age is actually an advantage… I think with a life well lived, you can lead more easily."

As well as offering a rare look into her personal life, Anna showcased a dry sense of humour throughout the interview. When director Greta talked about feeling like people couldn’t have fun when she was around, in her capacity as ‘the boss’, Anna remarked, "I know that feeling."

She added, "The art of the drop-by is also good. You go for five minutes and head for the hills."

In another moment, when Anna is asked if she’d ever have been able to swap jobs with Meryl, she self-deprecatingly shared, "I have no gifts. I have absolutely no gifts at all. I can’t sing, I can’t dance, I can’t act, I’m useless with my hands, I can’t cook, I certainly can’t sew."

Meryl, refusing to let such a powerhouse of a woman diminish her light, very quickly replied, "You run a multinational corporation, that’s all…"

And on this topic of women owning their accomplishments and power, the two discuss if it's necessary for a woman to have to dress a certain way to command respect.

Anna shared that the days of women dressing in power suits - the old idea of dressing like a man - is a thing of the past.

"I don’t think wearing a power suit to the office is in any way necessary. Think about the women that one admires: Mrs. Obama comes to mind. Whether she’s wearing J.Crew or Duro Olowu or Matthieu Blazy’s Chanel, she always looks like herself."