Beyond Trends: 10 Timeless Fashion Must-Haves for Women Over 50

Last Updated on May 11, 2024 by Candi Randolph

Question: Have we not all stood in front of our closets, swimming in a sea of clothes, and thought, “I have nothing to wear”? It’s almost like a rite of passage once you hit the fabulous 50 and beyond. I know. I’m in my 60s and it happens to me. But what if I told you it doesn’t have to be this way?

Imagine a closet where just about every piece is a superhero, ready to save your day (and your outfit). Yes, it’s possible, and I’m here to spill the tea on the 10 Fashion Must-Haves that will transform your wardrobe from “meh” to “wow”!

10 fashion must-haves for women over 50

Now, before you think this is another one of those lists telling you to shrink yourself into uncomfortable trends, think again. We’re talking about timeless pieces that hug you back, shoes that whisper sweet nothings to your feet all day, and accessories that make you shine brighter than a diamond. These are the trusty sidekicks that promise to work harder than a cup of coffee on a Monday morning.

Ready to meet your closet’s new best friends? Buckle up, girlfriend, because we’re about to elevate your style game—effortlessly, elegantly, and with a sprinkle of fun.

If you click on a link and then make a purchase, I may earn a small commission at no additional cost to you. Thank you!

10 Timeless Fashion Must-Haves

example of an outfit with fashion must-haves for women over 50

This outfit hits all the must-have marks: blazer, black tunic top, jeans, and black booties

Before we go any further, I have to say that this list of suggested must-haves is subjective. It always is. Most of these are on my list of favorites and I wear them again and again. They’re classic and will never go out of style.

Having said that, your preferred favs might look a little different, and that’s perfectly okay. But you know what? You might find a piece or two from this list that will elevate your preferences, so keep an open mind, my friend.

And, everything suggested here is for all sizes, shapes and ages. None of us have a perfect figure, we just learn how to take what we have and make it look awesome. If you’re stopped in your tracks thinking that fashion has left you far behind, take a few minutes to check out my very simple but effective email series course, The Fashion Cure.

1 | The Humble White T-shirt

The simple white t-shirt – who knew that the secret weapon in your fashion arsenal would be something so… well, simple? Yet, here we are, singing praises for this unsung hero that somehow manages to be everything we need and more.

First off, let’s talk versatility because this piece is like the Swiss Army knife of your wardrobe. Brunch date with the girls? Pair it with a midi skirt and those killer sneakers we mentioned earlier. Suddenly remembered you have a video call with the family? Throw on that tailored blazer, and voilà, you’re looking sharp without even trying.

And for those days when you’re feeling adventurous, why not knot it at the waist over your favorite summer dress? The possibilities are as endless as your creativity.

But it’s not just about versatility; it’s also about comfort and confidence. There’s something about slipping into a soft, perfectly fitted white t-shirt that feels like a warm hug. It’s the comfort food of fashion – always satisfying and never disappoints. Whether you’re running errands or meeting a friend for coffee, you’ll feel effortlessly put together.

And can we talk about the confidence boost? There’s a certain je ne sais quoi about a woman who can rock a simple white tee and make it look like the height of fashion. It screams, “I know who I am, and I’m fabulous,” without saying a word. It’s understated elegance at its best.

2 | The Well-Made Black Tunic Top

Alright, why is a well-made black tunic top a non-negotiable for us stylish women of a certain age? For starters, it’s like that one friend we all have – reliable, looks good in any situation, and always makes you feel comfortable. Whether you’re running errands, catching up with friends, or having a cozy dinner at home, this piece has got your back.

Picture this: You pair it with leggings for a look that says, “I’m here to relax but make it fashion,” or throw it on with some tailored pants and suddenly, you’re the epitome of chic sophistication. And jewelry? Don’t get me started. From statement necklaces to those delicate earrings you love, everything pops against a black canvas.

But here’s the kicker – it’s not just about looking good (though it certainly succeeds there). It’s about feeling good. That perfect black tunic flatters every figure, skimming over your curves and offering just the right amount of comfort without sacrificing an ounce of style. It’s like it was made with a magic wand, whispering, “Go ahead, rock your day.”

This is where I get my black tunic tops from – check it out!

In a world where fashion can be all too fleeting, the black tunic top stands as a testament to timeless style. It’s proof that some things never go out of fashion, especially not confidence, comfort, and that unbeatable feeling of knowing you look absolutely fabulous.

3 | Great-Fitting Jeans

Ah, well-fitting jeans, the unsung hero in the saga of our closets. You know the type – they greet you like an old friend, snug in all the places we love and forgiving in the ones we’re learning to love. It’s like they come with a built-in promise: “I’ll make you look fabulous, no matter what day it is.”

Now, why do we love them so much, you ask? Simple. Their versatility knows no bounds. Picture this: It’s a casual coffee catch-up with friends, and there you are, rocking your jeans with that perfect white tee we talked about, looking every bit the epitome of cool and casual chic.

Fast forward to an evening out, swap the tee for a sparkling top, slide into your favorite heels, and bam – you’re ready to turn heads. And just like that, your trusty jeans have transitioned from day to night without skipping a beat.

But here’s the secret sauce – finding that pair that fits just right. We’re talking about the kind of fit that makes you do a double-take in the mirror because, yes, you’re looking that good. It can be challenging to find that perfect fit, but I have a wonderful resource for you. I buy all of my pants from Measure and Made, and you might want to do the same!

It’s about celebrating your shape, owning your style, and strutting your stuff with confidence. Because when you find that perfect pair, it’s not just your outfit that gets an upgrade; it’s your whole vibe.

Remember, in the quest for those perfect jeans, it’s about how they make you feel. When you slip them on and they hug you just right, it’s as if they’re saying, “Go on, conquer the day. I’ve got your back.” And really, what more could we ask for from a piece of clothing?

4 | A Tailored Blazer

Wouldn’t you love to have that magic piece in our wardrobe that whispers, “I’ve got this,” no matter the occasion? Enter the tailored blazer, your new secret weapon for nailing that effortlessly chic vibe.

Picture this: it’s a laid-back Sunday brunch with your favorite people, and there you are, turning heads in a blazer that says, “casual elegance” without trying too hard. Fast forward to Monday, and that same blazer is now your armor in the boardroom (if you’re still on the clock), exuding confidence and professionalism.

It’s not just a piece of clothing; it’s your versatile bestie, ready to add that finishing touch of polish to any outfit, anywhere.

5 | The Versatile Skirt

Who among us hasn’t stood in front of our closet, sifting through a sea of clothes, and thought, “I have nothing to wear”? Enter the skirt – whether it’s knee-length, midi, or any other style that tickles your fancy. It’s like that friend who’s always there for you, ready to make your day just a bit brighter (and more stylish).

Now, why should this piece hold a coveted spot in your wardrobe? Well, first off, skirts are the chameleons of the fashion world. Got a lunch date? Pair that knee-length number with a crisp blouse, and you’re embodying sophistication. Transitioning to an evening soirée? Swap the blouse for a glittering top, add some statement jewelry, and voilà – you’re the belle of the ball.

But here’s where it gets even better. Skirts aren’t just about looking good (though they certainly excel in that department); they’re about feeling good too. They whisper sweet nothings about freedom and comfort, all while ensuring you look put-together. It’s that magical blend of style and practicality that we’re all searching for, isn’t it?

And can we talk versatility? A midi skirt, for example, is not just a piece of clothing; it’s a canvas for your personal expression. Dress it up with heels for that touch of elegance, or keep it casual with flats for a day of errands – either way, you’re making a statement that’s uniquely you.

6 | The Simple Longer Length Cardigan

Have you ever had one of those days where the weather just can’t seem to make up its mind? You step outside, and it’s a bit chilly, then suddenly the sun decides to grace us all with its presence. Well, friends, this is where the longer length cardigan becomes your best friend. It’s like that reliable pal who says, “Don’t worry, I’ve got you covered,” quite literally.

Now, why is this cozy gem a must-have, you ask? Picture this: You’re wearing your favorite top, the one that makes you feel like a million bucks, but there’s a nip in the air. Enter the long cardigan – not only does it keep you warm, but it also adds an effortless layer of chic to your outfit. It’s as if you’ve just stepped out of a high-fashion magazine while actually just trying to stay warm. Who knew practicality could look so good?

But here’s the kicker – the versatility. Whether you’re dressing up for a dinner date or keeping it casual for a day of errands, the longer length cardigan is your go-to. Pair it with jeans and a tee for a look that’s effortlessly cool, or throw it over a dress to add some warmth to your evening ensemble. It’s the fashion equivalent of a Swiss Army knife.

And, can we talk about comfort? Slipping into a soft, enveloping cardigan is like receiving a warm hug – it’s comforting, it’s soothing, and frankly, it feels like a little act of self-care. On days when you need that extra bit of comfort, this is the piece that not only keeps you cozy but also ensures you’re doing it in style.

In essence, the longer length cardigan isn’t just a piece of clothing; it’s a statement. It says, “I’m here, I’m fabulous, and yes, I’m comfortable too.” It’s about walking out the door knowing that whatever the day throws your way, you’ve got an ace up your sleeve. Or should we say, a cardigan in your closet?

You’ll find lots of ideas about how to wear and layer cardigans here, including longer length.

7 | The Little Black Dress (LBD)

The little black dress (LBD) – where would we be without this fashion superhero? It’s the piece that has been saving us from those “I have nothing to wear” meltdowns for decades. Whether it’s a last-minute dinner invite or a high-stakes work presentation, the LBD is your knight in shining armor… or should we say, matte jersey fabric?

This isn’t just a dress; it’s a canvas for your personality to shine. Dress it up with a statement necklace and heels that mean business, or keep it cool with a denim jacket and those classic white sneakers we all adore.

The beauty of the LBD lies in its versatility. It’s like a chameleon, ready to adapt to any setting while keeping you looking like a million bucks.

But here’s the best part: slipping into your LBD is like stepping into a bubble of confidence. It’s that piece in your wardrobe that says, “Look out, world, I’ve got this,” even on days when you’re not feeling 100%. It’s more than just a dress; it’s a boost of confidence, a hint of mystery, and a whole lot of fabulous rolled into one.

I have two LBDs in my closet – one for warmer weather and one for cooler weather. I’m always prepared! Check out these posts and find your perfect little black dress:

So, next time you’re staring at your wardrobe, wondering what to wear, remember that your LBD is there, ready to make you look and feel unstoppable. Because, in the end, it’s not just about the dress; it’s about how it makes you feel. And girlfriend, it makes you feel invincible.

8 | Classic White Sneakers

Oh, the classic white sneakers – where do I even begin? These beauties are like the Swiss Army knife of the fashion world. Not only are they screaming style with their sleek, clean lines and that oh-so-crisp white, but they’re also champions of comfort.

You know the drill – you’re looking fabulous for a coffee date with the girls, and next thing you know, you’re in an impromptu race with your grandkids at the park. And guess what? You’re winning, both the race and style points, thanks to those trusty sneakers.

But it doesn’t stop there. White sneakers have this magical ability to blend seamlessly with practically any outfit. Pair them with a flowy summer dress for that chic, carefree look, or throw them on with your favorite jeans for a classic vibe that never fails.

They’re the ultimate accessory that says, “I’ve put thought into my outfit,” while also whispering, “but I’m ready for whatever adventure comes my way.”

It’s like they’re the best friend in your wardrobe, always ready to make your day a little brighter (and your feet a lot happier). Whether you’re navigating the aisles of the grocery store or stepping out for a casual lunch, those white sneakers are there to make sure you’re doing it all in style and comfort.

Plus, they’re the perfect excuse to ditch those heels without sacrificing a single bit of that fabulousness. Who knew practicality could look this good?

9 | Stylish Booties

Whether they’re in classic black that goes with literally everything or in that rich brown that somehow warms up your entire look, booties are the unsung heroes of our wardrobes. You know what I’m talking about, right? That pair of booties that makes you think, “Why yes, I did wake up looking this effortlessly chic.”

First off, the sheer versatility. Heading out for coffee on a crisp autumn morning? Slip into those black booties with your favorite jeans and a cozy sweater. Or maybe you’ve got a dinner date, and you’re looking to add just a hint of sophistication without going overboard. Guess what? Those brown booties paired with a midi dress are about to become your new best friend.

But it’s not just about looking good (though, yes, that’s a pretty big part of it). It’s about feeling confident. There’s something about finding that perfect pair of booties that seems to say, “Go ahead, take on the world. You’ve got this.” And isn’t that just the kind of pep talk we need some days?

Now, here’s a little secret: the right pair of booties can also whisper sweet nothings of comfort to your feet. Gone are the days of sacrificing comfort for style. The modern woman knows she can have her stylish cake and eat it too – or, in this case, walk around in it all day without once thinking, “When can I sit down?”

So, whether you’re drawn to the classic allure of black booties or the warm, earthy tones of brown, remember this: investing in a pair (or two, who’s counting?) of stylish booties isn’t just about adding to your shoe collection. It’s about giving yourself a daily boost of confidence, comfort, and, yes, a generous helping of style. After all, who said practicality and fashion couldn’t walk hand in hand?

10 | The Versatile Trench Coat

Ladies, who among us hasn’t glanced at the sky, seen those clouds gathering, and thought, “Here we go again”? Ah, but that’s where the trench coat comes in – not just any coat, mind you, but a beacon of style in the unpredictable sea of weather.

It’s for those days when Mother Nature is feeling a bit moody, and you need something that says, “I’ve got this,” whether it’s warding off a chilly breeze or an unexpected drizzle.

But, oh, it’s so much more than a mere shield against the elements. Slip into your trench coat, and you’re immediately enveloped in a layer of unmistakable chic. It’s that perfect piece that ties your whole outfit together, turning what could have been a run-of-the-mill day into a runway-worthy moment. And isn’t that just a little bit thrilling?

We’re not just talking about staying warm here; we’re talking about doing so with understated class and style. With its classic lines and undeniable elegance, the trench coat is like that secret ingredient in your grandmother’s recipe – you can’t quite put your finger on why it works, but boy, does it make all the difference.

Whether you’re pairing it with those well-loved jeans for a look that’s effortlessly cool or draping it over your shoulders during a night out, the trench coat is your steadfast companion, ready to elevate your look with its blend of practicality and panache. It’s about striding out the door with confidence, knowing that, come rain or shine, you’re making a statement that’s all your own.

Check out these options that I curated just for you:

Add the Accessories

The Quintessential Accessories

We’ve danced through the wardrobe staples, but what about the cherry on top? Accessories! Yes, those delightful little additions that can transform “just another outfit” into “where did you get that?”

First up, Scarves. Think of them as your outfit’s best friend. They come in all shapes, sizes, and, most importantly, textures. A silk scarf can add a pop of color to a neutral outfit, while a soft, woolly one is like a warm hug on a chilly day. Plus, they’re perfect for those moments when you’re looking in the mirror thinking, “This needs… something.”

Next, we cannot forget about Statement Jewelry. Whether it’s those bold earrings that peek out just so under your hair or a chunky necklace that says, “Yes, I did wake up fabulous,” jewelry is your go-to for adding a personal touch. And the best part? There’s no such thing as too old for a bit of sparkle.

Then there are Handbags. Oh, where would we be without them? From the practical tote that carries, well, practically your whole life, to that sleek clutch for nights out (or, you know, just to feel fancy going to the grocery store), a handbag is not just about carrying your essentials. It’s about carrying them in style.

And finally, Belts. Yes, belts! They cinch, they define, and they can completely change the silhouette of an outfit. Plus, they’re a sneaky way to add texture or a dash of color right where you want it.

Now, remember, the goal isn’t to dress like a Christmas tree (unless that’s your jam, then by all means). It’s about choosing the right accessory, at the right time, for the right outfit. It’s the finishing touches that say, “I know what I’m doing,” even if you’re just winging it. Because, aren’t we all?

And there you have it. With these accessories in your arsenal, you’re not just ready to step out the door; you’re ready to make an entrance.

Fashion Must-Haves for the Over 50 Woman

Wrapping up our little fashion tour, we’ve covered the gamut from the trusty black tunic top to those stylish booties that practically scream “fashionista on the loose.” Each piece we’ve discussed isn’t just a must-have; it’s like a trusty sidekick in your style adventure – ready to make every day a bit more fabulous.

Now, you might be thinking, “Do I really need all these?” Well, imagine standing in front of your closet on a Monday morning. The coffee hasn’t kicked in yet, and you’re wondering what on earth to wear. That’s when you’ll thank your lucky stars for these versatile, timeless pieces that have your back, no matter where the day takes you.

Remember, fashion over 50 isn’t about adhering to a set of rules or blending into the background. It’s about owning your style, playing by your own rules, and feeling great while doing it. These 10 essentials are just the beginning. They’re your toolkit for expressing yourself, feeling confident, and yes, turning heads because, why not?

So go ahead, mix and match, experiment, and most importantly, have fun with it. After all, fashion is about expressing who you are, and you, my friend, are absolutely fabulous.

Like this post? Share it!

2 thoughts on “Beyond Trends: 10 Timeless Fashion Must-Haves for Women Over 50”

  1. I really enjoy reading your ‘Inspire My Style” and look forward to its arrival in my inbox. I always feel as if you are talking to me. Thank you for your ideas and inspiration. ♥

Leave a Comment

Your email address will not be published. Required fields are marked *

Scroll to Top