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?
The current style icons who share my body type are not people I admire.
Instead, I’ll choose bold eyewear like Iris Apfel, but in a colour and shape that suits my face. I’ll wear pants and tops that would make Katharine Hepburn happy (and her straw hat in the summer). I’ll style my hair in a pixie cut like Audrey Hepburn. Jackie O., I love those sunglasses.
My style is a mix of other people’s style. No “style words” or special icon for me.
Jennifer Aniston has great hair and tasteful, classic clothes that are nicely fitted to her well toned figure.
Although I disliked the fur scarves, I loved Joan Rivers fashion. Wearing bright nail colors as a senior, she did red carpet elegantly, and 3 layered tops well. Miss her insane comedy as well.
Thank you for showing us the beautiful fashion icons. I also pay attention to Kate Middleton, for me she is the epitome of classic style, starting with the Spanish riding boots to the J Crew slacks to gorgeous ensembles with not only meticulously co-ordinating outfits but with her family as well, and the colors!! She can wear them all but she really nails how to make the “look” happen wearing a variety of deep royal colors or other more unusual & earthy tones. Hair too, she has made subtle changes that are very fashion forward. You may have to read between the lines sometimes to catch the understated British commentary. LOL
Excellent post today. Trying to figure out what these icons had in common and it seems to me that they are all comfortable in their own skin. Which translates to their wardrobes. Food for thought for sure. Thank you.
Yes!
Sofia Coppola. Carolina Herrera. Carolyn Bessette Kennedy. Stevie Knicks. Deborah Harry. Bowie
As far as missing one, no, you nailed it. You could talk about Cher but she is out of reach and unavailable for real people events. This was a fun post.
Cher is amazing!
My style icons were Chanel and Jackie Kennedy in the sixties. In the seventies I was in college, raising four rambunctious sons and working part time at the hospital. I made my clothes then. I remember mid rise wide leg pants and a long matching vest. No frills, and like now, a simple almost masculine look for a small feminine woman. Now, my style icon, is you Jennifer. With my own twist. I rarely wear jewelry. I find it uncomfortable. But I prefer neutrals, solid colors in shades of blue, grey or off white. I wear a lot of jeans and prefer a straight leg now in dark washes. I like a column of color and never wear black. Navy is my dark color. Comfort is very important to me. My feet insist. Where we live, the style is extremely casual and often cowboy which I don’t wear. We do evolve with our own needs in mind.
Excellent blog. Great ideas.
Great article Jennifer! We are on a similar wavelength right now as you will see in my post tomorrow! Adore Helen Mirren and Alie Macgraw!
They are fabulous!
So interesting and insightful. Thank you!!!!
Love all these style icons, partly because they lived (and were photographed) during my lifetime. As a true petite (5 ft+, less than 100 lbs) I can’t carry off the full Diane Keaton, Iris Apfel, or Ali McGraw “look” but I can add some of their elements to things that look more trim on me……which makes me think that “trim” makes it to my personal style mantra. I might also think about Audrey Hepburn……..although for most of my adult life she was retired from much public view.