Who Is Your Style Icon? Lessons from Diane Keaton’s Menswear Style
I was once asked who my style icon was. At first, quite a few women came to mind. But when I really thought about it, one name stood out: Diane Keaton.
I have long admired her sense of style — particularly her iconic menswear look in the film Annie Hall. Fun fact: she reportedly had it written into her contract that she could choose what her character wore. That authenticity shows. The wardrobe didn’t feel like a costume. It felt like her.
And that’s exactly why her style has endured.
Diane Keaton and the Rise of Womenswear Inspired by Menswear
In Annie Hall, Diane Keaton popularized a menswear-inspired aesthetic for women: tailored trousers, waistcoats, oversized blazers, ties, crisp white shirts, and structured hats. At the time (the late 1970s), this was bold. It blurred traditional gender lines in fashion and redefined femininity.
But what made her style so compelling wasn’t just the clothing — it was how she wore it.
She didn’t dress in menswear as a trend. She dressed that way because it reflected her personality. Structured, confident, intellectual, slightly quirky — her clothing reinforced her identity.
That’s the essence of personal style.
Style isn’t about copying someone else head-to-toe. It’s about recognizing what resonates with you and adapting it to suit your body type, lifestyle, and comfort level.
Diane Keaton influenced my own wardrobe in the 1970s — I will share more about that in my 1970s fashion journey (coming soon)
How to Wear Menswear Without Looking Masculine
One common question women ask is: How do I wear menswear without looking too masculine?
The answer lies in styling and accessories.
Menswear silhouettes — tailored blazers, trousers, vests, and button-down shirts — provide structure. But structure doesn’t eliminate femininity. It simply shifts the balance.
Here are a few ways to soften menswear pieces:
- Choose fabrics with movement (silk blouses under blazers)
- Define the waist with subtle tailoring
- Add texture (velvet, tweed, or satin accents)
- Incorporate statement jewelry
- Wear a brooch
And that brings us to one of Diane Keaton’s most recognizable styling tricks.
How to Wear a Brooch with Menswear
One signature accessory that helped define Diane Keaton’s menswear look was the brooch.
Whether it was an oversized carnation pinned to a lapel or a vintage jeweled brooch placed against a structured blazer, that single accessory transformed the outfit.
A brooch does something subtle but powerful:
- It draws the eye upward toward the face
- It adds sparkle, softness, or color
- It personalizes an otherwise tailored look
- It blends masculine tailoring with feminine detail
Even when she wore a tie — another traditionally masculine piece — she often paired it with a brooch. That layering of masculine and feminine elements created visual interest and individuality.
Wearing a brooch on a blazer lapel, at the collar of a crisp shirt, or even pinned at the knot of a tie can elevate a simple outfit into something intentional and artistic.
It’s one of my favorite looks.
Why Menswear Style Works at Any Age -Especially Over 50
Menswear-inspired fashion is particularly appealing because it is:
- Timeless rather than trendy
- Flattering for many body types
- Comfortable and practical
- Easy to build into a capsule wardrobe
A well-tailored blazer or structured vest never truly goes out of style. Unlike fast fashion trends, these pieces anchor a wardrobe for years.
Menswear-inspired fashion is particularly flattering for women over 50. Structured blazers and tailored trousers create clean lines without clinging. A brooch draws attention upward toward the face — something many stylists recommend as we mature and want to highlight our features rather than our waistline.
Unlike trend-driven pieces, menswear staples feel polished and intentional. They offer confidence without trying too hard.
And the brooch? It’s one of the most versatile accessories you can own. Vintage brooches, floral pins, abstract metal pieces, or heirloom jewelry each tell a story.
Brooches are also having a quiet resurgence in modern fashion. Styled on denim jackets, coats, scarves, and hats, they provide personality in a way minimal jewelry sometimes cannot.
How to Find Your Own Style Icon Inspiration
So, who is your style icon?
Is it someone known for bold color? Minimalism? Classic tailoring? Romantic silhouettes?
Instead of copying their wardrobe, ask yourself:
- What elements of their style appeal to me?
- Is it the structure? The confidence? The simplicity?
- How could I reinterpret that in a way that suits my lifestyle?
Style is deeply personal. Diane Keaton didn’t follow trends — she followed herself. That consistency is what made her influential.
Take a thoughtful look at the person whose fashion taste you admire. Study the patterns in how they dress. Then consider what might work for you.
Menswear Style Is About Confidence
Menswear for women isn’t about dressing like a man. It’s about borrowing structure, confidence, and timeless tailoring — then adding your own signature.
For Diane Keaton, that signature was often a brooch.
What will yours be?