La-Di-Da, Diane: How the Original Girl Boss Served Up Tennis Chic, City Style, and Fearless Reinvention

If I’m being honest, Diane Keaton may have shaped more of my life than I’d like to admit. Specifically, Baby Boom Diane Keaton — JC Wyatt, the high-powered New York executive who traded boardrooms for baby bottles and somehow made both look glamorous. She was the original girl boss before we even had the term. I didn’t just love her; I wanted to be her. From checking real estate listings as a hobby (long before Zillow made it a sport) to tackling corporate America, to eventually building my own brand, I can trace so much of that drive — and style — back to her.

And then there’s her fashion. The blazers. The turtlenecks. The perfectly rumpled ease of someone who doesn’t need to try too hard. I’ve spent most of my adult life chasing that balance — the polish of JC Wyatt with the effortless cool of Annie Hall.

That Annie Hall tennis scene lives rent-free in my mind. Diane on the court in pleated white shorts and a crisp button-down, her swing more enthusiasm than precision, her presence somehow impossibly chic. There’s something so endearing about it — she’s stylish but human, the picture of awkward grace.

Then comes the post-match moment. Racquet tucked neatly into her tennis bag, she’s caught off guard when Alvy Singer strikes up conversation. Nervous, fumbling, disarmingly herself, she laughs her way through small talk before letting it tumble out: “La-di-da, la-di-da, la-la.” Completely improvised. Totally unforgettable. That single line — offhand, unpolished, and utterly real — became a cultural anthem for anyone who’s ever tried to play it cool while falling headfirst into something unexpected.

Her characters — from Annie Hall to Baby Boom — were women who did things. They built lives, took chances, made messes, and wore hats that didn’t match their shoes. Diane Keaton made it okay to be many things at once: ambitious and sentimental, awkward and elegant, funny and fierce.

For me, she’s the blueprint. The reason I love a good blazer, a black loafer, and a city that never stops reinventing itself. The reason I believe that style and substance aren’t opposites — they’re partners. Like love and work. Like tennis and life.

La-di-da, Diane. La-di-da. 🎬🎾