what to wear over 50

What To Wear Over 50 That Combines Style and Comfort

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Rather than adhering to a strict set of style rules, incorporating passing fashion trends, or succumbing to societal expectations, navigating the world of fashion over 50 is about something far bigger and more important: embracing your unique style and finding pieces that bring out your confidence! The real advice among all of the style “secrets” out there? There’s so much more to fashion than fleeting trends, mini skirts, and crop tops! Together, we’ll find the perfect balance between comfortable and empowering elegance, creating your own paths toward timeless pieces and personal expression. 

Consider this your personal style guide, where we share style tips and empower one another to embrace our individual style and our best version, all while celebrating the elegance, wisdom, and timeless charm that defines fashion beyond 50. After all, the best thing we can wear is our confidence – and we’re here to ensure it shines as brightly as your wardrobe choices. You’ve come to the right place – let’s get into it!

As we slowly begin to think about transitioning away from the cooler months and, consequently, our winter wardrobes, I’ve put together a list of easy, quick outfit ideas that combine both staple winter pieces and new closet additions that effortlessly blend style and comfort.

1. wide-leg pant + cotton shirt + coat + slingback pump + skinny belt

what to wear over 50

pants | shirt | coat | pump | belt 

Classic pieces make up this first outfit that’s perfect for a variety of occasions – from the office to an elegant daytime outing and even a drink date post-work

These wide-leg pants provide comfort while also making for a flattering fit with their high-rise design. Four-season stretch fabric keeps you mobile and looking put together all day long, and a slightly cropped length makes these pants the ideal choice as we slowly begin to phase out our winter boots (looking at you, West Coast!). 

A classic white button-up shirt might not immediately seem like the most versatile clothing piece in the world, but I beg to differ! Small styling tweaks can make this shirt an ideal choice for drastically different looks or even times of the day.

If you’re headed for lunch with friends, I recommend you wear this poplin shirt slightly open at the front, with your sleeves rolled to your elbows and tucked into your pants. This quick and easy transition makes this look a perfect contender for a day-to-night moment. 

Finish off the base of your outfit with a skinny black belt that serves to secure both your shirt and your pants in place, while also adding a chic and effortless touch of style. 

Layer this classic foundation with this Italian cocoon coat as a way to add not only warmth but also a touch of classic style and subtle pattern that adds character and charm to your look. Finish things off with the perfect shoe for this look – a slingback pump that is both comfortable and ultra chic. 

2. linen tee + v-neck sweater + straight-leg jean + loafer + tote canvas bag 

what to wear over 50

tee | sweater | jeans | loafer | bag 

Putting together simple and elegant outfits is all about selecting the right pieces, taking into consideration elements such as proportion and color scheme. 

This outfit starts with a simple base: a white tee and the perfect pair of jeans. A wardrobe staple is a staple for a reason, and these two pieces do just as they promise – create a basic, effortless base that’s the perfect starting point for tons of different looks. 

These high-waisted, straight-leg jeans are known for their great fit, made from premium organic cotton that provides support while still allowing you to move comfortably throughout your day.

On top, layer this v-neck sweater blazer, the perfect blend between a relaxed cardigan and a more structured jacket. The result of this style is an elevated design that adds effortless structure while still maintaining an elevated everyday feel to this outfit. 

For shoes, keep things comfortable and elegant with these simple loafers, and a touch of modernity with a canvas tote that is spacious and fashion-forward.

3. button down shirt + cashmere crewneck sweater + stripe drape pant + cap toe pump

what to wear over 50

shirt | sweater | pants | pumps

I love layering for every season, but there’s something extra charming about a classic button-down popping out from a simple sweater.

For chilly – but not frigid! – weather, this super classy outfit bets on a subtle but eye-catching pop of color. Start with a simple Oxford-style shirt, layering a cashmere crewneck over the top.

For styling, make sure to cuff both sleeves together in order to end up with clean, cuffed sleeves that show off the color of the shirt. On your neckline, gently straighten out the collar of your shirt over your sweater, effortlessly blending both pieces into one classy look. 

Pair these top elements with a striped high-waisted drape pant for a subtle and understated pattern, and finish things off with this cap-toe ballet pump. Not only do these trousers add some seamless movement to your outfit, but they also allow your shoes to peek out in just the right way! 

4. midi skirt + linen blouse + leather shoulder bag + mule

what to wear over 50

skirt | blouse | bag | mules

Just like other midi skirts, a simple a-line design can be easily styled all year round, making it the ideal transitional staple. If you’re already starting to get a taste of warmer weather where you live, this outfit might be right up your alley. 

Featuring an asymmetrical and pleated front design, this skirt contributes structure to your look while still keeping your outfit flowy and comfortable. A built-in belt allows you to achieve the perfect fit every time, and side seam pockets make this piece even more special. 

Pair this classic silhouette with this delicate linen blouse, another style that can be subtly styled for different looks, moods, and occasions. For this casual yet undeniably sophisticated look, I recommend tucking in the skirt and rolling the sleeves up slightly! 

Finish off with two gorgeous accessories I have a feeling you’ll be returning to often – a soft structure shoulder bag and chic heeled mules. 

5. boat-neck t-shirt + wool pant + crew sweater + penny loafer

what to wear over 50

t-shirt | pants | sweater | shoes

Elevated basics are mentioned often on my page, and this simple, basic t-shirt is the perfect example of what I refer to when I use this term. A slightly different boat-neck design takes this t-shirt to the next level. While basic pieces are great – and very essential for a complete wardrobe! – having slightly elevated versions of tees, for example, can give us the refresh we need. 

Pair your t-shirt with these black pants from Banana Republic, perfect for elongating your silhouette and bringing subtle movement to your look. For a little variety amongst neutral colors, I suggest tying this cotton crew sweater over your shoulders for an effortless, elegant touch. 

Finish off this simple staple outfit with a pair of classic black loafers. Having returned to the fashion spotlight over the last few years, this style brings both a truly timeless appeal and a current touch to your overall look. 

6. sweater lady jacket + way-high jean + leather mule + chain necklace

what to wear over 50

jacket | jeans | mules | necklace

If you feel intimated by patterns, stripes are a great example of one that allows you to bring in some visual interest to your closet while still keeping things classic. 

This sweater jacket blends two beloved silhouettes, resulting in a refined piece that can stand on its own to create a gorgeous look. 

On the bottom, a pair of dark denim takes this outfit in a more relaxed and casual direction without letting it lose its chic essence. A high-waisted fit and premium cotton fabric offer equal amounts of elegance and support throughout your day. 

Accessorize with a layered chain necklace, adding a delicate touch that matches the button detail on your sweater, and finish off this look with a pair of leather mule sandals that balance out the color palette of the ensemble seamlessly. 

7. wool flannel pant + cashmere sweater + leather tote + ballet flat

what to wear over 50

pants | sweater | tote | shoes

Dressing comfortably for a laidback day with your family doesn’t have to mean sacrificing style that makes you feel just as confident as you do relaxed! The truth is, even the most basic and simple outfits can turn into fashion statements if done well. 

These flannel pull-on pants exemplify just that, featuring a tapered leg and an elastic waistband for equal parts refined style and true comfort all day long. Easy to wear and style!

Go for the monochrome route by pairing these trousers with a gray cashmere sweater. The boxy fit of this particular style makes for the right proportions, subtly but effectively elevating your look. 

For accessories, we are once again keeping things simple and classic. A pair of black ballet flats will keep you supported and comfortably on your feet all day, while this large leather tote features a two handle design to be easily worn two ways.

When it comes to formulating the perfect wardrobe, there are a few things worth investing on, and a quality tote bag is one of them! Made from Italian leather, this investment piece weathers beautifully throughout the years, gaining character of its own. 

8. sweater dress + knee-high boot + hoop earrings

what to wear over 50

dress | boots | earrings

While we all (rightfully) love a little black dress, there’s another staple in the dress department that’s makes our lives just as easy and stylish as that famous wardrobe essential. 

For a foolproof and stress-free winter look, sweater dresses are always great options. Easy to wear and style, this particular midi design features mock neck and sleeve details that further make it an outfit on its own. 

Complement with knee-high leather boots, making for an instantly classic look. Additional features like a wide, block heel make this classy look just as comfortable as it is sophisticated.

For a final touch, add a pair of gold hoop earrings to bring it all together while keeping the look timeless and chic. 

9. slip skirt + long sleeve t-shirt + boyfriend blazer + cap toe ballet flat

what to wear over 50

skirt | t-shirt | blazer | shoes

Made from gently rumpled satin, this skirt starts off this look with its gorgeous texture and eye-catching movement. With a well-thought-out design, this piece is both form-fitting and flared at once, hugging your figure in all of the right places while still keeping you supported and comfortable.

On top, pair your skirt with a simple long-sleeved t-shirt that complements the outfit without detracting from the main event. Layer a slightly oversized black blazer on top, creating contrast with your other more delicate pieces and elevating this look with style. Pro tip! Finding a great blazer can be a quick and easy way to dress up a variety of basic outfits. 

Finish off with these stunning cap-toe flat that brings the elements of the outfit together with its golden sheen.

10. taper pant + slingback flat + leather belt + double-gauze shirt + crossbody bag

what to wear over 50

pants | shoes | belt | shirt | bag 

This next look is another super versatile option for daily wear that can also easily be dressed up or down depending on the occasion.

These pants kick things off with their tailored look and pleat details. Falling at ankle length and featuring a tapered leg, these trousers also come with a super high-rise that encourages a great fit beyond pairing well with any slightly shorter top. 

Next, this double-gauze shirt provides a fun new take on the classic cotton button-up, giving off a chic but unique look to this outfit. While I love the tucked-in look, this shirt would look great styled in an even more laid-back way without losing its elegant essence.

Roll up your sleeves, wear it slightly open at the front, and try tucking in only half of the shirt at the front; this might take a little trial and error, but a quick adjustment takes this outfit from serious to relaxed in just a few seconds!

For shoes, keep it classy and comfy with these stunning slingback flats. Since the color palette of this outfit leans on neutral rather than bringing in bright colors, shoes are a great way to bring in some texture and pattern without having to commit to too much. The crossbody bag – that can also be worn as a clutch! – brings in a deeper shade to this look, adding even more dimension to the final product.

Finally, add a belt to this look in order to balance both the color of the bag and the gold hardware details throughout! 

Want even more tips on mixing elegant and casual styles? I have a free checklist for you – among other freebies!- that you can get by signing up here.

11. button-up shirt + linen pant + Mary Janes + leather tote + earrings + gold watch

what to wear over 50

shirt | pants | shoes | tote | earrings | watch

Personally, I believe that flowy fabrics and designs can make for some of the most chic outfits out there, and that is especially true when you pair them tastefully with a few of your favorite accessories. 

This all-black look focuses on creating a relaxed silhouette that gives off elegance and movement as it falls. Beyond rolling up the sleeves to your preferred length, the rest of the styling is truly up to you!

While this is a longer-length top, the combination of these pieces really makes it a versatile look in more than one way. Whether you want to tuck in your shirt at the front or leave it be, this look truly adapts to whichever way you feel your most confident. And that’s what it’s all about, right?

Gold accessories like this dainty gold watch and knot earrings give us the delicate yet eye-catching details we want, lending an even more sophisticated yet effortless flair to the ensemble. Top it off with a comfortable pair of Mary Jane flats and a mid-sized, structured bag that ties with the accessories and brings structure to an otherwise laidback look. 

12. tee + high-waisted pant + long cardigan + mule + skinny belt

what to wear over 50

tee | pants | cardigan | mules | belt

This look brings in yet another pair of beautiful drape pants (can you tell I love this chic, versatile style?). Working to both flatter and elongate the silhouette, these comfortable trousers pair beautifully with a simple black tee for a put-together yet not-too-formal look. For an added detail, a skinny Italian leather belt adds its own delicate touch.

On top, this long cardigan provides both style and warmth to this easy go-to look while keeping things both elevated and perfect for every day. 

Integrating animal print into an outfit might be a controversial style decision for some, but I firmly believe there are plenty of ways to integrate this pattern in a way that is stylish, chic, and timeless.

For those looking to add a little extra personality and charm to their looks, subtly integrating a print like this through a shoe or a different accessory is a fun way to do it! For this look, I’ve decided to go with a heeled mule for an unexpected dash of style.

Cheers to Aging Gracefully and Knowing What to Wear for Women Over 50!

We all know how difficult it can be to get a hang of your perfect style and truly figure out what works and what doesn’t! Through these outfits, I hope you can see just how many options there are not only for different looks but for different pieces that can be styled in a wide variety of ways.

Regardless of your body type or age, the only thing that is important to remember is that the best styles are the ones that make you feel like you. 

I hope these outfits can serve not only as a little inspiration for your closet, but also as a testament that style knows no age. It’s all about finding joy and confidence in the way you dress. After all, just like us, our sense of style is always evolving – it’s a good thing we have each other!

Ready to start the journey of self-discovery and owning your sense of style? That starts with overcoming common struggles. I’ll help! Keep reading: Can You Relate? 13 Common Fashion Struggles for Women Over 50 and How To Overcome Them


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making mychicobsession.com a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.