Deep Style: Diane Keaton

On the heels of a new memoir about fashion, beauty and everything in between, Diane Keaton parses her style of a thousand layers for Briony Smith

When I ask the legendary actress Diane Keaton what inspired her new book of essays, Let’s Just Say It Wasn’t Pretty, the words bubble out, fizz gushing to fill the space between ice cubes in a glass. She chatters for nearly five minutes without stopping: the beauty in her mother’s laugh and Abraham Lincoln’s face, Melissa McCarthy’s comic genius … just a small sample of the millions of things that together make up a life of form over function.

Everything in Keaton’s book comes back to beauty, whether she’s finding it in unexpected places (the introduction is titled, fittingly, “Wrong Is Right”); seeking it in fashion, history, culture, architecture, design or nature; or wrestling with the lifelong challenge of creating some simulacrum of it herself through a spectacular, specific sense of style.

Gallery: Diane Keaton through the years

“The essays are about my eccentricities. How did I become this kind of person who fell in love with hats, who loves big shoes? How much can I cover up? What is covering up me? What does it mean to other people?” she says. “The book is trying to say to people: love what you have.”

The 12 essays la-di-da about, meandering from Keaton’s first forays with a Maybelline eye-shadow kit to pondering cosmetic surgery. (She hasn’t had any, but it’s not out of the question.) “I go back to the idea of the collage,” she says of this writing MO. Keaton is also obsessed with Pinterest, hoarding images of faces, fashion, books and libraries (but no food or table settings!)—and lots of interiors, because she flips houses obsessively. “There’s something so seductive about buildings. The feeling of ownership, though, doesn’t turn out the same way as dreaming of having all these places. I’ve become this serial renovator.”

She’s also quick to point out imperfections of her own. Keaton thinks her nose too crooked, hair too fine, eyes too hooded. Style has been her saviour. “We all say certain things about ourselves and go, ‘OK, I accept this about myself.’ And, obviously, I didn’t do that and so I had to figure out a way to be the best I could with what I had. I started to develop my own tastes.” A strong work ethic inherited from her civil engineer father and a dictum of “make work play” drummed into her by a childhood piano teacher spawned a future sartorial strategy. Thus, she donned turtlenecks (hide the neck!), granny glasses (cover those eyes!) and hats (what fine hair?). Today, Keatonisms like the ever-present chapeaux, huge belts and fingerless gloves occasionally land her on worst-dressed lists, but she doesn’t mind. As a teen, she’d watch TV programs that showcased the common trope of the nerdy girl who wins the boy’s heart by getting a makeover. Keaton realized long ago that she always preferred the before look to the after: “I wanted to be interesting and unique, and I didn’t want to have the makeover—ugh, who cares about that?”

After an earlier infatuation with Doris Day, Keaton’s girlhood scrapbooks swelled with photos of the crisp striped shirts and herringbone jackets of her style mentor, Cary Grant. “He seemed to own the whole world,” she says. “He was dashing and he was charming and he was funny and he was fabulous—who doesn’t want to be all of those things?” She carefully copied down his fashion credos (the tautness of a tie knot is paramount) and ethos: Clothes make the man.

Annie Hall’s vests, ties and trousers, all Keaton’s own, made her one of the most famous on-screen fashion icons of all time; her obsession with menswear has endured to this day. Sharp tailoring, she says, “makes me feel snappy! You feel like you can handle things, you feel confident.” Her favourite designers include Thom Browne and Paul Smith, along with Prada. “Nowadays, menswear designers, they’ve got the shorter jackets, the shorter pants, they really look good. The shoulders are narrower. I love tuxedos, formal wear, tweeds. I love it all.”

Her attire veers into avant-garde on occasion. “If I get up in the morning and have an idea, I’ll go with it,” she says. Let’s Just Say It Wasn’t Pretty recalls her sashaying about town in a giant pair of light-grey snow pants, which she picked up at an outlet in Utah while shooting a movie there. “I thought, These are great. I’ll wear them low,” she tells me. “You could hear them while I was walking. It was ridiculous. I thought that would humiliate people, but it didn’t: it was my bare feet.” Her doctor scolded her after she broke a toe strolling about sans footwear; fortunately, shoes are also one of Keaton’s great loves, whether it’s a gorgeous pair of orange strapless Prada pumps (that she regrets giving away), saddle shoes from the Woody Allen drama Interiors, polka-dotted disco boots, Yves Saint Laurent platforms, two-tone Tony Lama cowboy boots she rustled up for Annie Hall or a killer pair of seven-inch Christian Louboutin heels. “You could call a good two-thirds of my wardrobe an impenetrable fortress,” she writes.

Despite her fondness for intimidating footwear and man-repeller ensembles, Keaton has attracted plenty of legendary males, including Warren Beatty and Allen, with whom she still strolls through New York on occasion, as well as Al Pacino, who comes off in the book as the true love of her life. She survived their 1990 breakup by swaddling up in “long-sleeved everything. Coats in the summer. Boots with knee socks and wool suits with scarves at the beach.”

Now 68, Keaton is a single mom to two teenagers: son Duke, 14, who calls his mother “Cheeks,” and daughter Dexter, 19—named after Cary Grant’s character in The Philadelphia Story. Dexter didn’t inherit her mother’s fashion obsession (despite being stuffed into “black leggings, matching cap, licorice loafers, and ebony socks” as a baby, and, later, a houndstooth boy’s suit and vintage cowboy boots). “She’s more of an athlete. What she wears, I couldn’t care less,” Keaton says. “I can appreciate someone who doesn’t like what I like.”