Diane Keaton: ‘I was told to become more feminine – it drove me crazy’

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I first read this piece back in June 2017 in *TopMob* magazine. It came out around the time *Hampstead* – that lovely comedy drama with Diane Keaton, Brendan Gleeson, and Lesley Manville – was released, and it really stuck with me.

You notice her style immediately – it’s instantly recognizable as Diane Keaton’s. Her look is as unique today as it always has been, and ever since her Oscar-winning role as Annie Hall in the late 1970s – a character Woody Allen wrote for her, reportedly based on their relationship – she’s been consistently considered a style icon.

Diane Keaton is known for her signature men’s hats, and today she’s wearing a light-colored one with black detailing. She first got the idea after seeing French actress Aurore Clément wear a similar hat on the set of *The Godfather* (where Keaton played Kay, alongside Al Pacino as Michael Corleone). Keaton used to find these hats at thrift stores like Goodwill or flea markets, but now she has them custom-made by Baron Hats in Burbank.

Diane Keaton’s style is distinctive and playful. She pairs high-waisted, tight trousers with black sandals and a wide belt – a look designed specifically for her. She often wears a long-time favorite: a black and white striped shirt with oversized cuffs. But what truly makes her style unique is how she disrupts this classic look with unexpected accessories – large, metal knuckle dusters, leopard print fake nails, and several chunky crucifix necklaces. She describes her jewelry as inexpensive, pieced together finds. The overall effect is surprisingly edgy, like a rock star—think Axl Rose—dressed by the high-fashion house of Chanel.

She has shoulder-length silver-grey hair and wears glasses. Her expression is often a mix of amusement and slight confusion. She tends to be self-deprecating and doubts herself, which makes it difficult for her to confidently promote her own work.

When discussing her new film, *Hampstead*, she doesn’t dwell on details. The movie centers on a widow who forms a connection with a man (Brendan Gleeson) who has lived off the land on Hampstead Heath for 17 years. She was drawn to the script by Robert Festinger because it featured a woman her own age, feeling lost in life, and then finding an unexpected chance for change – something she believes happens to all of us. She appreciated how a single action could open up a new opportunity.

She hasn’t found romantic love – she’s never been married – but she’s found joy in being a mother. Twenty years ago, she adopted her daughter, Dexter, who is now 21, and later, her son, Duke, who is 16. Despite the challenges of motherhood, she feels content. Though she admits to worrying about her children – a concern that visibly upsets her – she often finds herself wondering if they will be okay, repeating the question with a troubled expression.

Diane Keaton tends to answer questions very briefly – a simple ‘yes’ or ‘no’ – or she’ll launch into long, rambling stories. When discussing uncomfortable topics, she becomes like her character in ‘Annie Hall,’ circling around the point with playful but evasive conversation. We discussed her struggle with bulimia during her twenties, while she was dating Woody Allen. She described it as an attempt to cope with deep unhappiness and an insatiable desire for… well, everything. She admits she still doesn’t fully understand the cause, but she stopped the behavior because she began intensive psychoanalysis five days a week – it had become a serious problem.

For a year, I kept something hidden from my therapist. Then, while lying down and avoiding eye contact, I suddenly confessed. I told her I knew I would never change, and surprisingly, she didn’t react. Her silence allowed me to finally stop hiding and move forward. I had become very skilled at keeping secrets.

She still has a pretty unique diet. Since giving up meat and fish, she mostly eats things like nuts and cheese – she really enjoys cheese! She explains that after struggling with bulimia for three years, her relationship with food became a little odd.

Diane Keaton was the oldest of four children, growing up in Santa Ana, California. Her father was a civil engineer, and her mother enjoyed photography. When Keaton was thirteen, she desperately wanted to take acting lessons and convinced her mother to pay for classes with local director Kenny Aiken. However, Aiken consistently left her out of his productions, which was very upsetting. He even told Keaton’s mother that she needed to attend modeling school instead, suggesting she wasn’t polished or feminine enough. Keaton was frustrated by this and stopped taking classes altogether.

She explains that she didn’t learn how to comfortably socialize growing up. While therapy helped her overcome her natural inclination to be withdrawn, it took work. She always felt a bit like an outsider, partly because her family wasn’t particularly social. She prefers to keep some distance and isn’t one to readily join groups. Although she values her friends and enjoys spending time with them, she still needs and appreciates a lot of alone time.

She often remembers childhood trips to Laguna Beach with her family. Her father, a passionate diver, loved the ocean, and they visited every weekend. She recalls one day seeing a lively party happening in a tent on the beach, which made her realize her own family wasn’t very social. As she remembers it, they were polite and friendly, but didn’t really connect with others in the same way.

While living in New York in her thirties, Keaton discovered a low-pressure way to socialize: volunteering at a Jewish home and hospital for seniors. She explains she felt a need to contribute, and these opportunities suited her because they involved a set amount of time, allowing her to be pleasant and engaging, then simply leave when finished.

I’ve started visiting my brother at an assisted living facility in Culver City – it’s close to where I live. It’s honestly been so good for me. It’s not just about seeing him, but also about connecting with the other residents and feeling like I can actually make a difference in their lives. It gives me a real sense of purpose.

She describes her mother as a very creative, kind, and supportive person. Her mother, Dorothy, actively helped her develop her unique sense of style. She recalls being playfully teased in high school for a memorable dress her mother made – it was black and white polka dots with a full skirt.

She’s lived in London on and off and thinks it’s the ultimate place for street style. She says people there don’t need to be rich to be fashionable – they just have great creativity and a strong sense of style. She contrasts this with Los Angeles, where she feels you only get noticed for your fashion if you’re a celebrity like Kim Kardashian.

She wonders if she still feels self-conscious about her appearance. When asked, she replies, “I always have.” She admits this insecurity likely never fully disappears, questioning if anyone truly feels completely confident. She sighs, adding that it would be wonderful to not worry about it, but acknowledges that she definitely still does.

She paused, then continued. “It’s a silly question, really. True happiness isn’t possible – if you think you’re happy, something might be wrong. There’s just too much sadness in the world.”

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2025-10-13 18:35