Diane Keaton Reflects on Her ‘Crazy Outfits’ Through the Years in New Book

Diane Keaton has been considered a style icon for nearly 50 years, since her menswear-heavy wardrobe in “Annie Hall” arrived on screens in 1977 and forever cemented itself in cinematic fashion history. Keaton, now 78, has loved clothes her whole life, and has remained an individual dresser through the years, still turning to menswear but also full skirts, wide-belted coats and hats — many, many hats. 

In September, Rizzoli will release “Diane Keaton: Fashion First” ($55), with a foreword by Ralph Lauren and commentary from the likes of Miley Cyrus, Kris Jenner, Sarah Jessica Parker and Candice Bergen. Keaton takes the reader through her first memories of fashion to her red carpet looks — and even breaking down some of her “wrong” fashion choices.

Here, WWD Weekend chats with the actress about the project. 

WWD: What made you want to do this book? 

Diane Keaton: That is the million-dollar question. I honestly never thought of it. I think when we started looking through photos of me on the internet we saw the humor in it but also the wide spectrum of loving clothes my entire life. It became a fit.

WWD: What was the experience like of going down memory lane and looking through all these photos?

D.K.: Terrifying and hopeful. What was I thinking? I got away with wearing some crazy outfits. No wonder people slam me for being eccentric. Gosh, I am lucky.

WWD: What does good style mean to you?

D.K.: Follow your heart. Express yourself. I don’t discredit anyone for showing their style.

WWD: What does being a “style icon” mean to you, and who is your style icon?

D.K.: I think of people like Cary Grant. He is a style icon. I wear what I like. 

WWD: How has your style changed over the years?

D.K.: Not at all. I still love a turtleneck, a hat and a jacket. I think I focus more on wearing suits daily than ever before. And wait…a wide belt.

WWD: Kris Jenner writes in the book she’d love to play in your closet for an hour — what do you think of Kris, and who is that person for you?

D.K.: She is a genius for being a successful manager. I respect that and I respect her hard work. I love seeing a woman in power. 

WWD: Were you surprised by the lasting fashion impact of “Annie Hall”?

 D.K.: Yes. I think it is a credit to the movie…not me.

WWD: Who inspires you fashion-wise?

D.K.: People on the street, to be honest. If you are asking me about designers it would be people like Ralph Lauren, Thom Browne and Celine. 

WWD: Ralph Lauren wrote the foreword for this book — how do his clothes make you feel?

D.K.: They make me feel good. He understands a woman’s body in a man’s style of suit. I simply adore him. He listens. Plus, he uses durable fabrics that adhere to a body yet keep structure. 

WWD: What is one trend you would never try? 

D.K.: Anything showing my body or my skin.

WWD: What is one item of clothing you’ll never part with?

D.K.: Turtlenecks.

WWD: What about one accessory?

D.K.: Glasses. They finish my outfit. 

WWD: What made you want to include a section of “wrong” looks? 

D.K.: The more we worked on the book we found humor in my choices. I mean hysterics. This is probably my favorite chapter. If we can’t laugh at ourselves, what is life about?