how to wear leggings over 50

How to Wear Leggings for Women Over 50: Outfit Ideas

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Today, we’re unveiling the world of leggings – a piece that is surprisingly versatile yet tricky to style… until now! Leggings might be our main focus, but they’re not all we’re discussing here; we’ll be tackling the art of styling them with sophistication, confidence, and, as always, some chic flair. After all, this piece can be worn by a woman of any age – all that matters is that it’s styled well and makes you feel empowered just the way you deserve. 

Want to know what makes this guide extra special? Our seasoned style expert is back! That way, she can bring in her first-hand experience as a part of our over 50 community.

over 50 style advisor

Into it? Then come along as we discover the secrets and style tips to donning leggings with elegance and poise. Whether you are a seasoned legging lover or just getting acquainted, this guide will get you going with all of the knowledge you need to get started. 

Feeling ready to step up your legging game? Let’s get into these looks – and Dr. Wood’s insights that you’ll get to see sprinkled throughout! 

1. slouchy tunic + leggings + leather loafer + crossbody bag + triple hoop earrings

tunic | leggings | loafers | bag | earrings

Though wearing leggings to the gym or lounging around the home may be the first places you think of to wear leggings (those are Wood’s favorites), they don’t have to be the only places. If comfort is what you’re after (without sacrificing style, of course), why not wear them out and about?

For those of us who still have some chilly days ahead before spring finally comes around, this first outfit is a great match! 

This first pair of leggings is a popular design, and it won’t take much for you to understand why. Start off your look with these ultra-wide waistband leggings known for their high-quality fabric that works to smooth and support, hugging your body for a flattering – but still comfy – look. These black leggings are as traditional as they get, and are perfect to integrate into your everyday outfits.

Next, this slouchy long tunic top is perfect for keeping you warm while earning you a few extra style points at the same time. Featuring a gorgeous mock neck and made from ribbed ottoman knit fabric, this piece seamlessly blends functionality and aesthetics. Similar to an oversized sweater or sweater dress, this piece makes for a stylish look with a comfortable fit.

If you’re not used to wearing leggings outside of the gym, then loafers might seem like a strange shoe choice, but stick with me! This classic pair of shoes effortlessly dress up this simple look without overdoing it, and sets you up for the perfect accessories.

Along with its subtle cream shade, the woven pattern in this bag softens the look, bringing in some welcome texture and visual interest to this otherwise all-black look. 

Elevate this outfit even more by adding these triple hoop earrings, tying together the gold hardware from both the shoes and the handbag for a chic, intentional ensemble that you can take anywhere. 

2. button-up tunic + Ponte ankle leggings + block heel + hobo bag

tunic | leggings | heels | bag

Despite the persistent cold climate where I live, I’m already dreaming of spring… and I know I’m not the only one! 

Depending on what the weather app is looking like for you, this outfit can be the perfect transitional look to rock while you are out running a few quick errands, grabbing a casual brunch with your family, or shopping around on the weekend. This reliable, functional, and comfortable look might become a new go-to soon enough!

When asked about whether more mature women should be able to wear leggings, Dr. Julie Wood responded with a firm “yes,” though she soon revealed her own preference when it comes to the piece, saying “I only wear them to the gym. […] At the gym or lounging at home.” 

If you also enjoy leggings but tend to keep them reserved for working out, outfits like these are the perfect way to get your toes dipped! This simple, casual look is a great choice for older women who want to experiment with the look of leggings. 

Begin putting together this outfit with these sleek and stylish pair of leggings. Made to be worn outside of the gym, this piece features design details such as raised seams that work to elongate your figure. Their longer silhouette and ankle split design detail make these leggings perfect to style with a (chic!) heel that you can comfortably walk in all day. 

On top, this linen and cotton button-up falls effortlessly over the leggings. While button ups can be styled a million different ways, this look calls for simplicity. Wear it as it! Beyond covering your lower body curves for comfort, this tunic also brings some subtle color and pattern into the look without compromising the neutral palette. 

Finish off the ensemble with a large slouchy bag that matches the shade of your twist heel for an added casual yet elegant touch. 

3. leggings + long sleeve + linen shirt + sneakers + crossbody bag + earrings

leggings | long sleeve | linen shirt | sneakers | bag | earrings 

Getting truly comfortable in your leggings doesn’t have to mean compromising on the style front! Even on busy days when style isn’t your number one priority, small little tweaks and choices can transform any outfit into something you feel amazing in. 

For the foundation of this look, pair these quintessential black leggings with a simple long-sleeved crewneck shirt. Beyond offering great support, these high-waist leggings are ideal for a number of occasions throughout your week.

Layer your linen shirt on top, wearing it unbuttoned and rolling up both of your sleeves together for an extra polished element.

Especially with casual outfits, accessories are a great way of bringing looks together and making them more interesting – all with minimal effort! This imported leather crossbody bag contributes both function and charm to this outfit, while square earrings add a delicate, feminine touch. 

These shoes fall perfectly in line with Dr. Wood’s idea of the perfect shoe when it comes to styling leggings, aligning with the idea of comfort and style behind this look: sneakers! High-quality, comfortable, and versatile, these shoes are the perfect staple sneakers for any minimal, neutral closet. 

4. faux leather leggings + oversized blazer + long sleeve top + mule + leather tote 

leggings | blazer | top | mules | tote

Leggings can be incredible staples in the sense that they are meant to be a true basic – they serve their purpose but don’t detract from the look. For those who want a little something extra, I recommend looking into options like these faux leather leggings! 

Also great for those who are after more support and figure-firming fabric, this design can be worn in tons of different ways. Their shiny finish gives any look a whole different feel, while still leaving room for other aspects of the look to show. 

Try pairing your bottoms with this cream-colored top. Especially when looking to style basics like leggings, small design elements in other pieces can go a long way in elevating the look; and this top does just that.

This long-sleeved shirt is the ideal layering piece, featuring a square neck, ribbed fabric, and a figure-hugging fit that keeps the final look clean while still contributing visual interest. 

On top, layer this oversized blazer. With a wider, boxy fit, this blazer plays with the proportions of the look and brings the right balance to the complete outfit. Able to be worn both open and closed, this blazer might become just as much of a staple as your leggings. 

Finish it off with a pair of leather mules that feature traditional gold-toned horse-bit detailing. On top of their classic appeal, these shoes are great for pairing with leggings because of their open back, which makes the transition between a tight calf fit and a shoe less drastic. 

For the cherry on top, this classic leather tote is here to pull it all together with its structured design and gold hardware. 

5. leggings + tunic shirt + slingback pump + bow belt

leggings | tunic | pumps | belt

Once again using this pair of leggings with elevated seams and an ankle-split detail, this look keeps things sophisticated and comfortable in its all-black color palette. When you are wanting to put together a fancier look, leggings are less likely to be part of your ensemble, though there are various easy ways to elevate this piece!

If you do find yourself looking for a way to upgrade your outfit, I suggest following the principles of Dr. Wood’s personal advice for dressing up a pair of leggings: “I try to wear nice athletic wear on top – tops that add a bit of coverage are especially good.” 

While athletic tops are great options for the gym, the concept of coverage is still something to consider when dressing up a more “formal” fit – even when it’s still casual wear! 

That being said, pair your leggings with this long tunic shirt. Featuring flowy material and side slits for unrestricted movement and comfort, this top pairs perfectly with a variety of black leggings. Make sure to check the size! This shirt tends to run larger, so adjust the fit to your personal preference. 

Two simple pieces are able to transform this look instantly. Starting off with our bow belt, this accessory cinches you in at the waist – as much as is comfortable for you – and gives the look good shape and structure. With the body-skimming fit of the leggings and the loose fit of the tunic, a belt is the perfect way to bring those two different elements together.

For shoes, a pair of kitten-heel slingback pumps elevate the feel of this look even more, taking it from something casual to a dinner-appropriate look you can dazzle in.

6. stirrup leggings + long sleeve crewneck tee + oversized bomber jacket + suede leather clogs

leggings | tee | jacket | clogs

I love creating classy outfits with leggings, but let’s be honest – they deserve to serve their casual purpose too.

This look is great if you are after a super comfortable outfit to lounge in during your rest days, while still retaining some of your personal style in your ensemble. 

These stirrup leggings bring some unexpected function and nostalgic charm to this leisurely look, keeping them fitting just right. 

On top, a long-sleeve crewneck makes the base of your outfit cozy while also incorporating somewhat of a brighter palette (did I mention I’m looking forward to spring?!). 

Layer this stunning quilted, oversized jacket over your shirt. Its shape is great for balancing the tighter fit of the bottom of the look, while also featuring a longer length that will keep your lower body curves covered for comfort. 

Perfect all year round, these soft footbed clogs will have you walking on clouds while adding a current touch to this ensemble. 

7. kick flare leggings + scoop neck sweater tank + wrap jacket + ballet flat

leggings | tank | jacket | shoes 

If you still are looking for a way to integrate leggings into your wardrobe without committing to the figure-hugging fit, this may be the right option for you! 

These self-titled elevated leggings feature more of a traditional pant look, while still keeping the comfort of the original design. Personally, this style is a great choice and sits somewhere around the top of my personal ranking system for women of all ages and body types.

Fitted through the thighs and hips, this piece is made from structured fabric that offers plenty of support on top and flares slightly from the knee down. With angled side pockets, these leggings are also functional for your everyday! For many, this specific take on the popular style brings even more options and versatility when it comes to creating looks. 

On the top, pair your leggings with this simple knit sweater tank, which provides high-quality material and adds a touch of white to the look. 

Layer this double-faced wrap jacket over your tank – this not only provides some warmth while we continue to inch towards spring, but it also gives this outfit a far more chic and elegant feel. Slouchy and structured at once, this jacket falls beautifully as it sits buttoned, allowing only the slightest touch of ivory to peek out from underneath. It’s the perfect way to keep things laid back while effortlessly dressing up as well. 

Finish off this look with a ballet flat, which matches both the comfort and the stylish feel of this outfit seamlessly. 

8. stirrup leggings + shirt jacket + ballet flat + tote + onyx earrings 

leggings | shirt jacket | shoes | bag | earrings

By now we’ve seen just how many different pieces can be styled along with leggings – and there’s even more out there!

Shirt jackets are another great style to search for if you are planning some outfits for the near future. Not only are they versatile when it comes to changing temperatures and transitional periods, but they are also traditionally made with longer silhouettes that make them the perfect pair for some comfy leggings during your week.

Usually made from thicker and more structured materials than a regular shirt, shirt jackets tend to naturally elevate the feel of an outfit almost immediately for this reason. This particular navy style is made from a textured cotton blend and features ivory buttons and patch pockets at the front. 

Pair with our previously seen leggings, this time with Mary Jane flats that really let you show off that fun and nostalgic stirrup detail! 

For accessories, there’s no going wrong with a classic, large leather tote bag that has got you covered no matter what your day has in store. These black onyx earrings bring some subtle sophistication to this casual chic look while still keeping things simple.

My Quick-Fire Expert Tips on How to Wear Leggings Over 50

While it can be helpful to browse and shop suggested styles, creating outfits from scratch can be an overwhelming task – which is why this guide is designed to help you get by. 

Before we wrap things up, let’s take a look at this list of quick-fire pro tips for choosing the right leggings for you every time…there may be more to consider than you think!

Choose High-Quality Fabrics

Opt for leggings made from high-quality fabrics, as good materials often provide better structure, support, and a more polished overall look. If you’re looking for a tried and true brand, consider Athleta. “Those are my favorite”, says Wood.

Go for Dark Colors

Darker colors, such as black, navy, or charcoal, tend to be more flattering and versatile. If you’re looking to get started with leggings, choose black, since they are the easiest to style a bunch of different ways while remaining chic. They can easily be dressed up or down, and tend to have a slimming effect as well.

Length Matters!

Don’t forget to take the length of your leggings into consideration before you hit purchase. Ankle-length or full-length leggings are more flattering than capris, especially if you’re going for a more sophisticated look as a more mature woman.

All About Balance – Pair with Longer Tops, Flowy Blouses, or Tunics

To achieve a balanced look, pair leggings – which are form-fitting by nature – with longer tops or tunics that provide good coverage for a modest and elegant feel. 

While this isn’t a must-obey fashion rule (are any, really?), pieces that are on the flowier side pair beautifully with leggings due to their contrasting silhouettes. 

Layer with Long Cardigans or Jackets

We can only have so many longer tops and tunics to go with our leggings! Layering gives us tons of other great choices when it comes to creating looks with this wardrobe staple – plus it can be done with a lot of the items you probably already have. This is a great option for those who would like to give leggings a try but still want to wear shorter tops. 

From long linen shirts and coatigans to blazers, the possibilities are endless when we start to style these staples with our leggings.

Choose the Right Undergarments

Regardless of what you are wearing your leggings with, picking the right undergarments is an important step that you need to tackle first.

Wear seamless or smoothing undergarments for minimal lines, great support, and unmatched comfort!


Shoes can be some of the most stressful parts of an everyday outfit that uses leggings. 

If you are trying to dress up, there is a wide variety of shoes available for you to pick from. Ankle boots, ballet flats, and low heels can pair beautifully with a pair of leggings (just think of what you love to wear with skinny jeans!). 

Steer clear of casual choices like flip-flops if you are after a more polished look. 

Customize Accordingly!

Just like every pair of jeans has its own distinct design features, leggings can too!

Make sure that you are shopping for the right kind of leggings while you browse online. Buying a pair designed for physical activity, for example, can mean a large logo, distracting (but functional!) seams, and other unwanted features that you’ll likely have a problem with. 

Learning to integrate a piece of clothing into our existing wardrobe can be a fun challenge, but remember that leggings don’t have to become your favorite overnight. If you’re looking for an alternative to leggings, try Dr. Wood’s suggestion, “Wear cute joggers that aren’t too bulky. In fact I have these Vuori joggers in about 6 different colors.”

At the end of the day, it’s about enjoying the experimentation process and seeing what truly resonates with you.

Wondering What To Wear Over 50 That Combines Style and Comfort? Keep reading!


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 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.