Fashion Over 50: 5 Best Style and Confidence Tips

Last Updated on February 2, 2024 by Candi Randolph

Hey, there! Let’s talk fashion and that fabulous over-50 flair—you know, where experience meets elegance and every piece tells a story? It’s high time we celebrate the unique style each body type brings to the table, and girlfriend, you’ve got a whole banquet of beauty.

So you’re not yet an ‘older woman’, but let’s face it, you’ve seen the fashion world evolve. You’ve witnessed trends come and go faster than that flirty two-week romance in Paris ’75. But guess what? Your sense of style? It’s only gotten sharper with time. Mature women like us, we’re not chasing fashion trends—we’re setting them with timeless elegance, nodding to classic styles while carving out our own.

fashion over 50 - 5 best style and confidence tips

Strutting into the second act of life is about crowning yourself with confidence. It’s about knowing the best way to highlight your strengths and strut your stuff, whether you’re rocking that power suit or slipping into those weekend comfy-chic vibes.

I’m here to spill the tea on some style tips and share a few style secrets that make us mature ladies the true icons of the fashion world. So, grab your favorite beverage and let’s explore how to curate a closet that celebrates every curve, corner, and color of you. After all, when has age ever defined us? We’re just getting started.

Just for grins, let’s ponder the phrase, Fashion over 50, itself. What is that? So, in the way that I typically do, I researched the phrase ‘Fashion Over 50’ to see what some of the top results were.

This is a sampling of what I found:

  • How to stay fashionable after 50
  • Must-have wardrobe pieces for women over 50
  • How to be fabulous at 50
  • Style guide and wardrobe tips for women over 50
  • First date fashion over 50
  • Best tips to look young over 50

Now, there is nothing wrong, in my opinion, with any of these statements. We all want to dress with confidence and know how to look good at 50 plus. If that is what you’re searching for, there are plenty of answers for you, girl.

I’ve written similarly about fashion over 50 and 60, very sincerely. The advice, tips and outfit suggestions I shared have been helpful to many women.

So what’s my problem? The fact that we search for suggestions with regard to how we should dress after a certain age is common, and I’m up for checking out some tips, advice and a how-to here and there.

But for me, there is not a set of rules that we must follow in order to fit that ‘over 50’ fashion definition or view of acceptability.

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Fashion Over 50 – Let’s Get Specific

So, have you ever stood in front of your wardrobe, pieces of your fashion history staring back at you, and thought, “What now?” You’re not alone. As an older woman, dressing up isn’t about keeping up with the teeny boppers and their crop tops. It’s about a classic style that plays to your strengths—knowing your best features like the back of your handbag, right?

Let’s set the scene: The little black dress. Yeah, it’s a no-brainer, but have we forgotten how amazing we feel in those? Pair it with some bright colors, like a colorful scarf, and you’ve got an ensemble that shouts confidence without saying a word.

And what about denim? Dark denim is our friend, our sturdy companion through thick and thin. Rocking the best jeans that flatter every curve is practically a rite of passage for us. Trust me, find that perfect pair, and you’ll wonder how you ever lived without them.

But let’s not skimp on the tops. A silk blouse? Oh, my, yes. It’s like the Swiss Army knife in your style arsenal—versatile, sleek, and always on point. A white shirt might seem plain, but believe me, it’s one of those classic pieces where less is decidedly more. Think of it as the canvas to your daily masterpiece.

Jackets? Longer jackets have entered the chat. They’re like that know-it-all friend who actually knows it all—their length works wonders for any body shape, adding a touch of sophistication, whether you’re commanding the boardroom or commandeering the brunch table.

Neutral colors are great and all, but a splash of color never hurt anyone. It can be the difference between “just dressed” and “dressed to kill.”

Investment pieces – yes, they might make your credit card cringe at first swipe, but they’re called ‘investment’ for a reason. That trench coat you’ve been eyeing? It’ll stand by you through drizzles and downpours, both meteorological and metaphorical.

With years of experience come miles of fashion inspiration. We’ve moved past dressing for others. It’s all about what feels good, what speaks to our fashion sense, and what amplifies the beauty of our favorite body parts.

Friends, every choice we make, every classic look we embrace, tells our story. So, let’s make sure our fashion choices reflect not just the women we are but the women we’ve always been destined to become. Now, who’s ready to work their wardrobe like the catwalk of life awaits?

Rediscover Your Personal Style in Midlife

The Fashion Cure

Fashion Over 50 | Dress with Confidence | 5 Best Tips

Tip #1: There are no black and white rules for what we should or should not wear as we age.

Over 50, over 60 and beyond, there are no absolutes.

Having said that, we might create some absolutes for ourselves, because WE decided to draw the line, not because a blogger or fashion editor said we should.

I know, for example, that I will not wear crop tops anymore, and tank tops, even though I love the comfort and have worn them for years, are probably heading to the ‘no’ list, at least for public viewing. 🙂

Even though I’m in pretty good shape and am not overweight, I am not comfortable showing certain parts of my body to the world anymore. But that is my decision, not because I read somewhere that women over 50 shouldn’t wear tank tops.

Tip #2: Our selection of clothes and accessories should reflect who we are on the inside and be an authentic expression of that.

If your personality and expression is bold and dramatic, and you can comfortably wear hot pink high heels with your skinny jeans, go for it! Dress with confidence!

My authentic style expression is pretty much what you see in the photo above. A bit understated, nothing real flashy, always comfortable, and with my own style expression. That’s me.

Tip #3: The level of confidence we possess will play a part in how we dress.

By the time we reach our 50’s, we should be totally in sync with who we are, inside and out, right? Well…for some, yes.

But for many women in midlife, there are still uncertainties and lack of confidence in many areas, with fashion being one of them.

Am I wearing the ‘right’ outfit for this function? Will the girls on the golf league think I look okay? Am I overdressed? Under dressed? Does my (fill in blank) look too large? small? Will this outfit make me look old??

We still tend to worry too much about what others think of us, and that, my friends, comes down to confidence in ourselves and our decisions, whether it’s fashion related or not.

Remember this. You are awesome, just as you are, today.

This doesn’t mean we are not motivated to become healthier or take care of our bodies. But it does mean that we confident of who we are now, we know how to look good at 50 plus, and that is reflected in how we dress.

Here are several posts I wrote that have been helpful to many women in defining their personal style over 50 as well as gaining confidence in selecting their wardrobe pieces:

Tip #4: Common sense is always a factor.

As with other areas of our lives, our fashion decisions should include the ‘common sense’ test. It may not be done consciously, but we all have our limits as to what we feel is right for us.

I can’t tell you what those limits are for you. But I know what they are for me. And if I’m not sure if a fashion choice is best for me…if I hesitate…ponder it…wonder if it is the outfit I want to show the world…then that is the answer. Don’t do it.

I will give this piece of fashion wisdom to you though, my friends. Invest in a hand mirror and always, always check the rear view before leaving home. Start with the hair and work your way down to the feet. Trust me. You want to do this.

Tip #5: We should do what makes us happy, and fashion decisions are no exception.

Trends in fashion are fun to check out, and some of us are really into it, like you fashionista girls. I think that’s awesome.

I’m not into fashion so much, though, so my idea of knowing what’s in style is to take a quick tour of the ladies clothing section at my department store of choice. But I’m perfectly happy doing that. I don’t really pay much attention to fashion for myself.

So, Fashion Over 50? What it means to me is making fashion decisions that make me happy, dress with confidence, and express who I am authentically as a woman and a person. How about you?

Final Thoughts: Fashion Over 50

Fashion Over 50 - What is That?

Alright, listen up, my fabulous friends! As we wrap this style session, let’s remember one thing: Being a mature woman (not defined as an older woman!) is like being a fine wine—you only get better with time. Your wardrobe? It’s your best friend, telling your story without spilling all the juicy details.

The only things standing between you and a killer outfit are the outdated ‘rules’ we’re tossing out the window. Whether you’re a mature woman who rocks pearls like nobility or the kind who can make a leather jacket look like the queen’s robes, there’s no denying—you’ve come a long way, baby!

Different styles are just chapters of your life. Some you might revisit (hello, vintage revival!), some you’ll keep forever (the perfect pair of jeans anyone?), and others, well, they were learning experiences, weren’t they? But, every stitch in time has led you to a new style, a great style, that’s all you.

Fashion is about finding what makes you feel like sunshine on a cloudy day. A great way to start? Look to those inspiring women around us—the ones who dress for themselves, who pull off real women chic with confidence that radiates stronger than any runway spotlight.

So, go ahead, rewrite the style narrative. Let every layer, every accessory whisper, “I’m here, I’m fabulous, and I’m just getting started.” Remember, fashion is the playground of life, and darling, the swings are waiting.

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18 thoughts on “Fashion Over 50: 5 Best Style and Confidence Tips”

  1. Thanks for the tips and encouragement to choose what works best for me as an individual. We are each individuals, so it’s great to get ideas, then adapt as needed to make the style one’s own.

  2. These are great tips. As I am wasting into my 40s I have shifted to more conservative cuts and more classic styles over trendy.

    1. I know what you mean, Carly. For most of us, our selections change as our bodies change, and it’s a good adjustment most of the time!

  3. These are great tips. I think a few of them can apply to other ages as well. Especially the one about our clothes reflecting who we are on the inside.

  4. I totally agree, Candi. There are so many fashion advice posts out there but for me, I need to feel comfortable in what I wearing. That doesn’t mean dowdy, it means that what I’m wearing feels right, I’m not conscious of something being too short or tight. When I wear the garment, I know that I’m going to look good and that makes me feel good. I’ve found since I retired it was difficult to find a look that would suit my new lifestyle, however, you can’t beat ‘Classic’ style and that is what I try to wear. Thanks for the tips and have a beautiful day. xx

    1. I agree, Sue! When you feel good and know that you look good, it’s the right choice. I’m a casually classic styled person myself most of the time. Thanks, as always, for stopping in! xo

  5. I’ve always struggled with clothing. Initially, I was always heavier than I wanted to be, so I felt insecure in everything I wore. After losing weight, I had a hard time finding “adult” clothing that didn’t make me feel like a teen. I love all of the pieces you recommend and the perspective that it’s all about “fashion decisions that make me happy, maintain my confidence, and express who I am authentically as a woman and a person”.

    1. Candi Randolph

      I’m so glad you found some inspiration from this post, Sarah! It really is about what makes you feel good and confident. 🙂

  6. Great advice and suggestions here. I’ve been slowly figuring out what my style is at this stage of my life. I went through a period where I was letting myself be too constricted by my age. And I think all it did was take some of the shimmer out of my life. I mean, it was just too boring! Now that I’m 56, I’m more comfortable taking the occasional risk if I feel good doing it – that’s all that matters.
    Joan Senio
    My Best Friend Adeline

    1. Candi Randolph

      You’re right, Joan! We may be getting older but we still can have fun with our styles if that makes us feel good. Thanks so much for stopping by.

  7. I’ve never shown off much of my body. That’s not because I dislike my body but merely because I’ve been shy to flaunt the chest and legs! I’m a classic style dresser and always have been, so not much change as the years have gone by. The only change I would say I have made in my mid-fifties is that my heels have got slightly.. lower.

    1. You have a classic, ageless style, Laurie and it suits you perfectly! You’ll probably still be wearing the same lovely outfits years from now…with slightly lower heels. 🙂 Thanks for stopping by.

  8. So well said, Candi! I really believe we should all develop our own personal style based on what we think looks good on us. By mid life most of us know what our best features are and how we can enhance them. If I have any doubts about an outfit, I’ll ask my husband. other than that I wear what I’m comfortable in. Sharing to FB.

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