How Diane Keaton Turned Her Insecurities Into An Iconic Look

When you think about Diane Keaton, words like "confident," "iconic," and "unapologetic" probably come to mind. She was one of those celebs who never missed with their signature style. The actor and fashion icon, who passed away in October 2025, was known for creating an entire aesthetic, making menswear both mainstream and cinematic for women as far back as the '70s. But what many don't know is that Keaton didn't do this because she lacked insecurities, but rather because she dressed through them. Believe it or not, the "Annie Hall" star once said she felt she had "ugly knees."

"I have always had a rough time with skirts, especially if they are too short," she wrote in her 2024 book, "Fashion First" (via The Gloss). Her solution to that insecurity was simple: Wear bottoms that went past the knee. Suits, she found, were perfect. The pants and sleeves were long enough to cover her up, and most importantly, they made her feel comfortable. "There are so many wonderful things to love about a suit. The pants don't have to be too tight. Neither does the jacket," she added.

Still, would a style icon truly be a style icon if she stuck to just one look? Keaton didn't think so, so she improvised. "If [skirts] are below the knee, I put an obscene amount of tulle underneath it to make it wide," she wrote. She'd even combine pants and skirts because she was "insane," as she described herself in a June 2020 Instagram video. This search for comfort evolved into a deep love for coats. "A coat is my version of a ballgown. A coat is perfection. It is like a cellar. I am hidden. I can relax in a coat, which is a blessing for a person like me who tends to be anxious and worried most of the time," she wrote in her memoir. Unfortunately, knees weren't the only part of Keaton's body that made her feel insecure.

For most of us, the solution to a bad hair day is tucking our locks under a hat or wig and hoping the hair gods treat us better the next day. But for Diane Keaton, who had a complicated relationship with her hair, things were different. "I desperately wanted to look like Raquel Welch," she wrote in "Fashion First," adding, "I could not get over her hair. The bounce, the curl, the height." Considering that Keaton had straight tresses and 1960s Welch often had waves and curls, there was quite a disconnect.

"I started wearing hats as soon as I realized I hated my hair," she admitted in her book. "A hat allows me to hide the worst part of the head. You know, that strange area from your eyebrows to your hairline. A hat is the final touch to a great outfit." Keaton wore bowlers and berets, and she even once sported a hat so large that it nearly touched the ground. "Is my new hat too big?" she teased in a June 2023 Instagram post. "Be honest."

On one hand, her fashion journey was a masterclass on how to cultivate a personal style if you have no idea where to start, as well as how to find a creative outlet that makes you feel comfortable. But on the other, her outfits sometimes seemed to become armor instead of expression. The good news is that the Golden Globe winner seemed to recognize this herself. "I'm trying to wear hats less often these days," she told AARP in May 2014. "I've let the dyed blond grow out to gray, and I like it. All I want is no alopecia, no female-pattern baldness and enough hair to last a lifetime. I think I've got it."

One theme that recurred throughout Diane Keaton's many interviews was her lifelong love for fashion. According to the actor and style icon, it started long before adulthood. "Even when I was young, I was way into fashion," she said in her 2020 Instagram video. "My mom and I used to pick out patterns, and then I'd tell her what I wanted, and she'd do it for me."

Designer brands weren't lining up to collaborate back then, so Keaton, her mom, and her sister found thrifting to be one of the most sustainable ways to update a wardrobe. "[My mother] took me to Goodwill and let me express myself," she told People in August 2024. The Academy Award winner also shared their creative process in "Fashion First," writing, "Mom and I loved to put an outfit together. We would assemble our idea, do my hair and make-up, and then head to the backyard (or even find some wall to pose up against in the neighbourhood) to take pictures. I miss my backyard photoshoots with my mom."

Even after the fashion icon made a name for herself, she passed that love of thrifting down to her son. "I went with my son last weekend to go thrifting. I picked up a styling pair of jeans. I think they were only $12.00!" she added to People. While it's a little bittersweet to realize that some of Keaton's genius was fueled by insecurities, there's no denying that fashion was an intrinsic part of her. Her bold choices reshaped what femininity could look like in fashion, and her unique style will always be remembered.