Style Icons to Inspire Your Wardrobe to Be Fun
There’s no shortage of style advice out there. Open any app, and you’ll be told to elevate your basics, refresh your neutrals, or buy something new you apparently can’t live without. It’s a lot of noise for something that’s meant to feel personal.
That’s why I pay attention to style icons.
Not because I want to copy an outfit from another decade, but because they cut through the clutter. They have a point of view. They repeat themselves on purpose. They understand that style isn’t about constant change, it’s about clarity.
The women below are interesting because they’re decisive. Their clothes feel intentional, consistent, and unmistakably theirs. And that’s exactly what makes them useful.
Diane Keaton: The Power of a Signature
Diane Keaton built her style around structure and repetition. Menswear tailoring, wide-leg trousers, crisp shirts, strong belts, and the occasional hat…worn not once, but over and over. What looks distinctive about her isn’t novelty. It’s commitment.
She understood early on that clothes could create authority. Tailoring gave her presence. Repetition gave her ease. By sticking to a narrow set of shapes and proportions, she removed guesswork and let confidence do the rest.
What to notice
Her style isn’t about mixing things up. It’s about editing down. Same silhouettes, same balance, different days. That discipline is what makes her look intentional rather than theatrical.
Borrow the idea
Look for wide-leg trousers paired with a crisp button-down or fine knit, then add a grounding piece such as a tailored blazer, vest, or substantial belt. Keep the palette simple. Let the structure do the work. She was also a fan of polka dots, which I’m seeing a lot of this spring.
POLKA DOTS TO TRY
Iris Apfel: The Queen of Maximalism
Iris Apfel was a walking reminder that getting dressed should feel like a creative act. Big glasses, layered necklaces, embroidered jackets, stacks of bangles. Nothing matched, and yet everything worked. Her wardrobe was a celebration of individuality.
What to take from her style
Style should bring you joy. There is no wrong way to get dressed if you feel like yourself in it. Iris never dressed to blend in. She dressed because it delighted her.
Try this
Add a colorful cuff to your everyday look. Mix two prints that feel playful. Try a statement necklace with your basic jeans and tee. You do not have to go full Iris, but letting your personality peek through your outfit is never a bad idea.
FUN BOLD CUFFS
Helen Mirren: Bold Meets Refined
Helen Mirren’s style is proof that you can age gracefully and still take risks. She plays with color, texture, and silhouette, but always in a way that feels sophisticated. She wore pink hair on the red carpet and walked in Cannes in a full cape. Yet she is just as comfortable in a sleek suit or an understated midi dress.
What to take from her style
Balance is key. Even when she goes bold, there is polish. Her outfits have shape. Nothing sloppy. But always with a twist.
Try this
Swap a basic coat for something in a bold jewel tone. Try a blazer with strong tailoring. Add a monochrome look, then finish with a red lip.
SOME BRIGHT COATS FOR SPRING
Ali MacGraw: Bohemian with a Quiet Soul
Ali MacGraw’s style has always felt like a breath of fresh air. Long before boho became a trend, she was wearing linen tunics, wide-leg pants, artisan jewelry, and anything that moved with her instead of against her. Even now, her wardrobe feels collected rather than curated.
What to take from her style
Comfort doesn’t mean giving up on style. Ali’s look reminds us that clothes can feel soft and lived-in and still make an impression. It’s about natural fabrics, relaxed fits, and pieces that feel like they’ve had a life of their own.
Try this
Reach for a flowy linen shirt, cotton pants with movement, or a softly printed scarf. Add a few silver or wooden bangles, slip into leather slides, and finish with a woven bag or an artisanal necklace.
ARTISANAL PIECES
Jackie Kennedy Onassis: Structured and Elegant
Jackie O mastered the art of looking composed without looking stiff. She favored simple silhouettes, clean tailoring, and clothes that always fit just right. From her shift dresses and pillbox hats to later years in oversized sunglasses and crisp white pants, she never looked like she was trying too hard.
What to take from her style
You don’t need much. When the fit is right and the lines are clean, the rest takes care of itself. Jackie’s strength was in choosing well and editing often.
Try this
Reach for a structured coat, a classic shift dress, or wide-leg pants in a neutral tone. Finish with oversized sunglasses or a sleek bag. The goal isn’t to look like Jackie. It’s to borrow her clarity.
Princess Diana: Polished with a Rebellious Streak
Princess Diana’s style journey is one of the most iconic transformations we’ve ever seen. She started out in ruffled collars and pie-crust blouses, very on brand for a royal in the early 80s. But as she grew more confident, her wardrobe evolved as well. Out went the frills. In came sleek column gowns, power suits, and the famous revenge dress. She learned to use clothing as a form of quiet communication.
What to take from her style
You are allowed to evolve. Your wardrobe should reflect where you are now, not where you started. Diana’s later looks were elegant, clean, and bold. She wore color well, tailored coats beautifully, and always looked intentional.
Try this
Reach for a blazer with a strong shoulder or a sleek sheath dress in a single color. Try elegant kitten heels instead of stilettos. And do not underestimate a good handbag. She always made a statement without saying a word.
Style Mistakes Even Icons Avoid
We often discuss what to wear. But what you choose not to wear says just as much.
Here’s what most of these style icons have let go:
- They don’t follow every trend. If it doesn’t suit them, they skip it without apology.
- They don’t let their clothes wear them. Confidence comes first. The outfit is just support.
- They don’t stop editing. Closets change with you. They stay intentional.
- They don’t confuse expensive with stylish. It’s about quality, not the label.
- They don’t forget tailoring. A well-fitting pair of pants or a jacket will do more than any accessory.
How to Use Style Icons Without Copying Them
You’re not trying to become someone else. The value of a style icon is noticing what catches your eye and translating that idea into your own wardrobe.
Start small. One element is enough. Maybe it’s a sharply cut blazer, or a bold piece of jewelry worn with otherwise simple clothes. Try it with what you already own and notice how it shifts the outfit.
Over time, patterns emerge. You may realize you’re drawn to structure, or ease, or restraint. Once you see that, shopping and getting dressed become more straightforward. You’re no longer reacting. You’re choosing.
You can admire someone’s style without adopting it wholesale. The goal isn’t imitation—it’s developing clearer judgment about what belongs in your closet.
Do you have a style Icon I missed, and what inspires you about her style?
Immensely enjoyed this article! Thank you.
Good Morning Jennifer: Great article today. And with such respected admirable fashion icons. I love a good statement piece necklace, that’s not over the top. I’m tempted to buy that bauble bar necklace …. but so many colors to choose from. Help! 🙂
Those are fun!
It’s lovely to see these unique, fashionable ladies! An article I read about Jackie O. many years ago had a big influence on me. The photos showed her wearing different colors of the same tailored shirt. She loved it so much it became a uniform for her for awhile. Back then, I envied how easy it was for men to dress for work ( suits being their “uniforms”) so Jackie inspired me to buy multiples of things I really loved to create my own consistent look. I still do this but in a much more casual way now.
Carolyn Bessette Kennedy is another style icon. She dressed in a tailored, simple but elegant…always elegant way. Her clothes from the 90s could easily be from 2026. Classic, tailored, timeless. That is the closest to how I dress today. Except, I’ve left above the knee shift dresses behind, preferring fitted maxi dresses after two knee replacements.
I do love her simple style too
I love your post today. What stylish women! I look at them and envy their poise and confidence.
I try to achieve it for myself but I don’t think I hit it quite right. Still, I keep trying!
As long as I try I feel better than throwing just anything on.
That’s the whole idea!!
Thank you for a lovely review and description. I enjoy putting together new looks, and your newsletter inspires even more creativity.
My inspiration is Melania Trump – true classic!
Shes always beautifully dressed. Very elegant!
Thank you for this insightful article. It discusses what we wear from a higher order of thinking. It is thought provoking and immediately useful. I think is is one of your best and I appreciate the time it must have taken you to create it.
I often look to Princess Katherine who is not in my age group, but has her own style and also communicates without saying a word.
Thank you, thank you.
She is so stylish! I love her gracious look.
I always admired the way Audrey Hepburn and Mary Tyler Moore dressed. I think because cigarette pants really suited me. Princess Diana was amazing. She could pull off anything. I’ve been wanting to do something bold and this post inspired me 😀
Yay!
I have always Loved Audrey Hepburn’s style! From Breakfast at Tiffany’s to Sabrina, her clothes were classic. I so NOT have her body type, but it doesn’t matter because her style was so transformative! Even later in life, she always looked so tailored, crisp and stylish!
Judy Dench is my style icon!
Thank’s for this! I’m stuck in my style….need to try harder!
Love this post
This was a perfect column….I have always felt too frivolous trying to explain this to people but you just made the perfect statement: “Style should bring you joy. There is no wrong way to get dressed if you feel like yourself in it.”
No matter how depressing the political or other social environment, I can look forward to getting dressed each day.
Dressing well is a great source of joy and self-care for me.
Just a comment and ad for bangles. I have very large wrists. I usually pass up on bangles. Any fine jewelry bracelets I have have normally had another link added. I have found that Chico’s bangles actually fit over my wrists! It is funny how pleased I am to actually be able to wear this jewelry.
Same, my hands are large so I like hinged bangles or ones in a C shape.
This was a perfect column….I have always felt too frivolous trying to explain this to people but you just made the perfect statement:
“Style should bring you joy. There is no wrong way to get dressed if you feel like yourself in it.”
No matter how depressing the political or other social environment, I can look forward to getting dressed each day.
I love all the looks! Breaking out of old ways is so difficult for me and seeing the looks on familiar faces doesn’t help 🤔 Forging ahead fearless!
I love Elyce Arons style. Her mantra is “Wear what makes you happy”!
Yes, she’s fabulous!
https://www.townandcountrymag.com/leisure/arts-and-culture/a64939199/kate-spade-elyce-arons-memoir/
Trish, thank you for your comment. Because of you, I will put it on my to read list of her new memoir, We Might Just Make It After All. Elyce Arons details life with, and after, her dearest friend, with whom she made fashion history.
It looks like a great book
Allie McGraw-I’m surprised when I read her name and that she is still alive because to me she passed away back in 1970 with “Love Story”. 😊
She’s very much alive and thriving.
Good morning? I absolutely enjoyed your post today. All the women you mentioned are my favorites, have a great day
Thanks!
So, so right. Thanks for stating so clearly
My inspiration is Coco Chanel. She said, “You can be gorgeous at thirty, charming at forty, and irresistible for the rest of your life.”
Thank you for this quote! Love it and love Coco!
That is a perfect philosophy!