Okay, so I’ve been totally obsessed with Diane Keaton’s style forever, right? It’s like, so effortlessly cool and chic, and I finally decided to try and channel my inner Diane. I call it “Diane Keaton Fashion First” – because, well, she’s the original!

Operation: Diane Keaton
First things first, I raided my closet. I mean, really dug through it. I was looking for anything that screamed “Annie Hall” but, you know, updated. Think oversized button-downs, wide-leg trousers, maybe a vest or two… the whole shebang.
I found a few things that could work: a cream-colored linen shirt that was definitely a bit too big (score!), some old black pants that were kinda baggy in a good way, and a surprisingly cool, slightly-worn-in men’s-style vest. Not a bad start, I thought.
Accessorize Like a Pro (or Diane)
Next up: accessories. This is where Diane really shines, you know? It’s all about the details. I remembered she’s a big fan of hats, so I grabbed a fedora I had lying around. It felt a little… Indiana Jones at first, but I figured I could make it work.
Then I added a thick, kinda chunky belt to cinch in the waist of the oversized shirt. It instantly made the whole outfit look more put-together, less “I just rolled out of bed.” And, of course, I threw on a pair of round-framed glasses. Because, well, Diane.
The Final Verdict
- Shirt: Oversized and linen – check!
- Pants: Wide-leg and comfy – double check!
- Vest: a little bit.
- Hat: Fedora for the win!
- Belt: Cinching it all together.
- Glasses: Round and quirky.
I looked in the mirror, and… I kinda loved it! It wasn’t exactly Diane Keaton, but it was inspired by her, and that’s what I was going for. I felt comfortable, confident, and like I could conquer the world (or at least, you know, go grab a coffee). I even have to put on my old brogues. It was perfect.

It’s amazing how just putting on a few key pieces can totally change your vibe. I definitely recommend giving this a try if you’re looking to spice up your wardrobe. And who knows, maybe you’ll discover your own inner style icon along the way!