You might be asking yourself what style has to do with confidence, especially at this stage in our lives. So many women over 50 give up on style, makeup, and clothes. They feel that maybe there is no point anymore. That how they look doesn’t matter. That style is for younger women. Or maybe it never was a big part of their lives, so why start now? So, hold on there girls, because style is much more than how you look. Style is about your confidence. It’s about how you project yourself when you walk into a room. It’s about how you feel, not just about how others see you. When was the last time you showed up for you?

 

Why Style Confidence Matters Now

Here’s the thing, chances are pretty good ladies, that you have spent decades taking care of everyone else. Decades. I know that I have.  But now that you are over 50, you might feel a little strange taking up your own space. Being You, without being Mom, Wife, Daughter, Friend. Just you. I know that when I got to that point, I felt a little lost about who I truly was. Me. My confidence was a little shaky. I wanted to be truer to who I was. To let people see I still mattered. I still had a voice. To see me. And one of the tools I used to set myself apart was style.

 

 

 

You can learn style confidence. I wasn’t born with it; I am not one of those women who spent a lifetime turning the heads in every room I walked into with my fashion sense. I’m still not. But if I can learn how to use style to boost my confidence and to project the me that I want others to see, so can you. Even Psychology Today admits, “style is a reflection of your unique complexity as a human being.” So reflect who you want to be. 

Midlife is the perfect time to set yourself apart, because as women, we are finally learning who we really are after 50. I love fashion, but I don’t live for it. I live for the feeling when you look in the mirror and think, “Oh hey, there she is.”

“Standing out doesn’t mean being louder; it means being truer.”

 

The Confidence- Style Connection

So how do we connect style and confidence? Think of the two as mirrors; one reflects the other. What you wear signals to the world how you feel about yourself. And how others see you. In fact, it can even affect how others treat you. 

5 Shifts in How We Think About the Style Confidence Connection

• Style should not be about dressing to fit in or to follow the trends, but about dressing to reflect you.
• You know how you feel when you are wearing an awesome outfit? When you feel good in your clothes, makeup, and accessories, you project that confidence to those around you.
• Style is a personal thing. How you express your style and how another woman does can be totally different, yet the feeling of confidence can be the same.
• As a woman 50+, you want to dress for your personal energy, not your age. And I don’t necessarily mean your energy levels, although that counts. I mean, you as a person on this planet. Are you bold or classic, loud or elegant? Most of us are a combination of lots of things. But if you are a minimal woman and feel you need to wear bright red lipstick even though it isn’t you, you won’t feel confident. You will feel conspicuous, and not in a good way. Because you won’t feel like you.
• Which leads me to this point. What you want to project to the world will change from day to day. I know for me, some days I feel most like myself in knee-high boots and sweaters, full makeup and a little jewelry, and I get a little confidence boost from my heels clicking across the floor. Other days, I love leggings, white sneakers, a baseball cap, and a ponytail. Both these things make me feel confident, for different reasons at different times. Rock what makes you feel good, that day, and the confidence will follow.

“Confidence doesn’t show up in high heels — it shows up when you do.”

 

The Myths of What We Are Supposed to Wear After 50

First of all, I hate rules. I homeschooled my kids, I started blogging when blogging wasn’t cool, I speak out (loudly) about things I care about, no matter who disagrees. Among other things. There are a ton of myths out there about what women of a certain age are, or aren’t supposed to wear. Forget them all. Here are some goodies:

Myth #1

Women over 50 shouldn’t wear… fill in the blank. Leggings, mini skirts, heels, animal prints… I could keep going. Anything sexy. Nonsense. We deserve to wear whatever makes us feel unstoppable.

Myth #2

When we pass a certain age, we should wear modest clothing. Don’t get me wrong, I believe in being polished, myself. But that doesn’t mean we have to dress like nuns. Or like Mrs. Roper from Three’s Company. (Unless that’s your jam, in which case, you go!) We are still sexy, we are still beautiful, and we are not treating aging like it’s a bad word anymore.

Myth #3

Comfortable clothes are sloppy clothes. Ok, just stop right there. I demand comfort in my clothes. I have, since I was a girl. My mom can tell you stories of all the clothes she bought me that I wouldn’t wear because they were scratchy, or had a scratchy tag. But these days I deal with several autoimmune conditions and am a highly sensitive person, so scratchy, uncomfortable clothes? That’s a giant no. And at this point, we have earned comfy clothing. But comfort doesn’t have to mean paint-spattered sweats and a torn T-shirt. 

 

 

 

Myth #4

You will look ridiculous wearing the latest trends.

When I was 13, I had an outfit that made me look like Belinda Carlisle from The GoGos. I mean, exactly like her. I remember that white mini skirt to a T. Would I do that today? Probably not. But there are ways to incorporate trends and still project the woman you are today.

Myth #5

Certain clothing no longer looks flattering on an aging woman’s body.

So first of all, can we all stop trying to dress for what’s “flattering” (meaning to impress others) and dress in what makes us feel wonderful? If you feel good in it, you’re confidence will shine, and that is more of what makes a woman beautiful than the clothes.

“Style is the Tool, Not the Topic”

 

How to Use Style to Reinvent Your Confidence (Without Forgetting Who You Are)

One of the things I don’t want women doing is to embrace someone else’s style. To compare yourself to another. It’s a trap my Middle Girl friends. You are never going to feel confident being someone else. So the trick is to reinvent your fashion, makeup, and accessory choices in a way that makes you feel wonderful, but still you. 

Ask yourself how you want to feel. What you choose to wear has everything to do with how you want to feel when you wear it. And again, this might change from day to day. But every woman is different as well. Some common ones? Pick one word from each section that best describes you.

 

 

✨ How You Want to Feel in Your Clothes

💫 Confident & Empowered

Confident • Self-assured • Strong • Capable • Bold • Radiant • Empowered • Free • Brave • Secure • Poised • Unapologetic • Grounded • Proud • In control

Feeling centered in who you are — and comfortable taking up space.

🌸 Comfortable & Effortless

Comfortable • Relaxed • Easy • Effortless • Fluid • Light • Natural • Peaceful • Balanced • Calm • Soft • Cozy • Simple • Breezy • At ease

Feeling at home in your body and unbothered by the world’s noise.

🔥 Playful & Creative

Playful • Fun • Curious • Vibrant • Expressive • Adventurous • Inspired • Artistic • Whimsical • Lively • Bold • Fearless • Modern • Spirited • Alive

Feeling open to try, mix, and play — style as self-expression, not perfection.

🌿 Authentic & Grounded

Authentic • Genuine • Honest • Aligned • True • Present • Mindful • Centered • Rooted • Calm • Purposeful • Intentional • Real • Serene • Steady

Feeling like yourself — no costume, no mask, just you.

💖 Feminine & Radiant

Feminine • Beautiful • Graceful • Elegant • Glowing • Alluring • Warm • Soft • Joyful • Sensual • Lovely • Compassionate • Delicate • Romantic • Magnetic

Feeling connected to your own beauty — inside and out.

Now ask yourself how you want to be seen. This is the second part of figuring out your sense of style. Again, pick one word from each section.

 

 

✨ How You Want to Be Seen in Your Clothes

💫 Confident & Capable

Strong • Self-assured • Empowered • Poised • Sophisticated • Put-together • Polished • Leader-like • Respected • Grounded • Secure • Commanding • Assured • Smart • In control

Seen as a woman who knows her worth — and dresses like it.

🌸 Elegant & Timeless

Graceful • Classic • Refined • Effortless • Chic • Understated • Balanced • Tasteful • Composed • Smooth • Sleek • Timeless • Serene • Harmonious • Cultivated

Seen as someone whose presence is quietly powerful and beautifully composed.

🔥 Vibrant & Bold

Magnetic • Dynamic • Fearless • Playful • Expressive • Spirited • Joyful • Adventurous • Daring • Modern • Eye-catching • Alive • Memorable • Radiant • Unforgettable

Seen as a woman who stands out with energy, creativity, and confidence — never apology.

🌿 Authentic & Approachable

Real • Warm • Relatable • Genuine • Down-to-earth • Friendly • Kind • Open • Natural • Honest • Comfortable • Easygoing • Inviting • Present • True-to-herself

Seen as a woman who feels both real and radiant — the kind of confidence that puts others at ease.

💖 Feminine & Empowered

Beautiful • Radiant • Alluring • Feminine • Gracefully strong • Sexy-in-her-own-way • Confidently sensual • Soft but powerful • Inspiring • Self-loving • Balanced • Compassionate • Elegant-with-edge • Empowered • Poised-in-her-beauty

Seen as a woman whose magnetism comes from self-knowing, not approval — a modern definition of feminine power.

So now that you have your 10 words, pick your top 3. I know, it’s hard. It doesn’t mean you will never use your other words; we are just trying to get a baseline of what your style will be all about.

For me? My 10 words were:

Confident- Comfortable- Expressive- Real- Warm- Polished- Effortless- Unforgettable- Easygoing- Beautiful

And my top three?

1. Confident
2. Polished
3. Beautiful (Which is a very personal thing, I mean beautiful to me!)

Now I have a firm foundation on which to make style choices that will make me feel how I want and to be seen as I want. Me. As I say. Not society. Not some style rule book. Me.

“When you wear what makes you feel powerful, you become the woman you already are — just turned up a notch.”

 

 

How to Build Style Confidence (Even If You’ve Never Had It)

So here comes the rubber meets the road moment. What do we do with the clothes we have in order to make us feel and be seen the way we want? The way that is true to us? I gotcha covered…

 

 

1. Start with One Power Outfit.

You know that outfit that just does it for you — the one that makes you stand a little taller? That’s your starting line. Keep it handy for the days when you forget how amazing you are.

 

 

2. Dress for Your Energy, Not Your Age.

Ignore “age appropriate.” Instead, ask: How do I want to feel today? Grounded? Bold? Playful? Whatever your answer, build your outfit around that.

3. Edit Your Closet with Kindness.

If it doesn’t fit your body or your life anymore, let it go. Keeping “someday” clothes only clutters your space and your confidence. Make room for the woman you are now.

 

 

 

4. Learn the Rules — Then Break Them Beautifully.

Understanding proportions and fit gives you freedom, not limits. Once you know what works, you get to bend every rule with flair.

5. Invest in Fit, Not Quantity.

A perfectly cut blazer or jeans that hug in all the right places will always outshine a closet full of maybes. Tailoring says, I care about me.

 

 

6. Find Your Signature.

Maybe it’s gold hoops, a red lip, or white sneakers with everything. For me, it’s boots and designer bags, mostly Kate Spade. (Bought on clearance!)  Your signature pieces tell the world, “This is me.”

7. Use Accessories as Little Pep Talks.

Every time you put on that favorite necklace or scarf, let it remind you who you are becoming — confident, bold, radiant. Accessories are affirmations in disguise.

 

 

8. Create a Confidence Capsule.

Pull together 10–12 mix-and-match pieces that make you feel instantly like your best self. Less chaos, more clarity — and a lot more confidence.

9. Practice Mirror Talk.

Instead of picking yourself apart, meet your own eyes and say something kind. She’s been through a lot and still shows up. That’s power.

10. Dress for the Life You’re Creating.

Even if you’re not there yet — wear what that future you would wear. Confidence often shows up the moment you decide to act like she’s already here. Photo from the incredible style blogger Alyson at That’s Not My Age.

 

 

Bottom line:
Style confidence doesn’t come from the clothes — it comes from the woman wearing them. Start small. Stay curious. And remember, you’re not reinventing yourself — you’re finally dressing like the woman you’ve always been.

“Style = self-trust made visible.”

 

 

3 Real Women Over 50 Who Set Themselves Apart with Style

Need some proof? These three women all have very different styles. Yet they all radiate confidence! It’s not what the outfit makes your body look like… It’s what the outfit makes your spirit look like. Your face. Your smile. Your strength.

 

 

The Inner Work Behind the Outer Glow

Now I am not going to lead you to believe that clothes and style are magic. That as soon as you put on that gorgeous black blazer or pair of leather ankle boots with that sexy (but comfortable) heel, you are going to be undeniably confident. Style is a tool. You also have to throw in some mindset work as well. But the thing is, that work is a lot easier when you have on that sophisticated collared sweater, or when carrying that sassy leather handbag. Things to work on?

• Remember that how you project yourself affects how you feel. According to the American Psychological Association, the facial feedback hypothesis by Charles Darwin (and many studies since) tells us that if we smile, even if we don’t feel like smiling, our brain reads that smile and actually starts producing those feel-good brain chemicals. Yes, fake it till you make it can work. So it makes sense too, that if you project who you are with the clothing you feel is right for you, the confidence will come. Some ways to help along that transformation?
• Recognize that it’s the confidence that people find magnetic; the clothes are just the wrapping. 
• Your smile, posture, and stance all contribute to how people see you. Picture a beautiful woman in the most elegant outfit you can imagine, but she’s frowning and slumped over, not meeting anyone’s eye. Now picture another woman, same outfit, with a confident smile, standing tall and walking down the hall like she means it. Which one is more magnetic to you?
• Know that there is more to building confidence than just what you wear. Take the time to do some inner work on your self-esteem, and the confidence will come. You can read more about that in my post How to Boost Confidence, Self-Esteem, and Self-Respect.

“You can’t fake confidence — but you can dress for the woman you’re becoming.”

 

Using Style to Reflect Confidence Without Apology

The last trick is learning how to set yourself apart with style, without apology. Some women feel that if they make a fashion or style change, people will think them ridiculous for trying too hard “at our age”. That’s crap. Own it. Style confidence isn’t about impressing anyone else; it’s about expressing who you really are. We’ve earned that right. Express yourself and do it without apology. Otherwise, the world wins by keeping older women in a box we didn’t earn. Break out of that box.

Start small. Try one small thing a week until you are more comfortable experimenting.

 

 

Have a mantra for yourself when you feel insecure. When I was first experimenting with style, I can’t tell you how many times I put on something I hadn’t tried before, thinking it looked amazing in front of my mirror, then panicked once I realized I was out in public and there was no going back. (It may happen to you, too. 🤣) You can try one of these, or invent your own.

💫 1. “I’m not dressing to impress — I’m dressing to express.”

A quick reframe that shifts the focus from approval to authenticity.

🌸 2. “Confidence first. Outfit second.”

Because when you lead with self-belief, everything else falls into place.

🔥 3. “I’m allowed to take up space — and look damn good doing it.”

A little cheeky, a little powerful — and exactly the energy midlife deserves.

 

 

What to Do From Here

I am a girl in The Middle, and I don’t just mean midlife. I don’t believe anything has to be all or nothing. You’ve already started on your style confidence journey by reading this post. You are arming yourself with knowledge, validation, and a little bit of sassy “she’s got your back”. (Because I do!) I know how many times in the past when I have felt insecure with changes I wanted to make, I just needed a cheerleader. Someone who was doing it, and saying “it’s ok for you to do this too. In fact, it’s more than ok, you deserve it!” If you are like me, I am happy to be that someone for you. So, here it is…

“It’s ok for you to do this too. In fact, it’s more than ok, you deserve it!”

Remember, style confidence is not about impressing others. It’s about expressing you.

So I want to leave you with a couple more tools you can use to help you create confidence with style. 

First, if you haven’t already gotten my free mini course, Style Confidence, sign up here now.

Next, check out a couple of my posts I think you might like!

Elevating Your Style After 50 in 3 Steps

How to Dress to Disguise

Want more tips on thriving after 50? Sign up for my newsletter and join our community of empowered women on Facebook and Instagram!

Feel free to share this post with others!

Also visit my Freebies page, where everything is… well, free!

Back to the Blog for more great articles!