How To Wear Leggings Over 50

Leisure wear is an essential part of any wardrobe. While we all love a good denim and top combination, sometimes we crave a more relaxed and lounge-friendly look that still feels polished. This is where leisure wear comes into play. It combines everyday wardrobe basics with athletic styles to create a sporty and chic appearance.

I once had a subscriber say to me, "Women in their 60s don't wear leggings," and I couldn't disagree more. Many women struggle with how to wear this style in a way that feels age-appropriate, but I believe leggings have no age restrictions—they can work for anyone! The key is in how you style your leggings to achieve a look that makes you feel comfortable and confident. In this blog post, I will show you how leggings can be stylish wardrobe essentials for women over 50.

If you enjoyed this post and want more ideas on how to expand your leisure wear, stay tuned! There may be an eBook in the works, and by signing up for the newsletter, you'll be the first to know!

Also, if you know a fabulous woman over 50 who struggles with wearing leggings and could use some tips or encouragement, please share this post with her!

 

#1 | Style With A White Button Up & Clogs

How To Wear Leggings Over 50

This combination is both chic and sporty. The white button-up shirt creates a polished look, while the clogs add an edgy and relaxed vibe. The baseball cap contributes a sporty touch to the outfit. Plus, you have the option to add a casual layer like this utility jacket or denim jacket. All of these items are part of your year-round wardrobe basics, as outlined in this eBook.  This outfit is perfect for lounging around the house, hosting guests to running errands!

Complete the look: baseball cap

#2 | Styling With An Oversized or Longer Blouse

How To Wear Leggings Over 50

Wearing leggings with an oversized blouse gives you coverage both in the front and back, providing the confidence boost you need when pairing tight-fitting bottoms like leggings. This combination perfectly blends a polished look with a sporty vibe, and the right accessories and jewelry can enhance and complete the outfit.

Shop these exact items: blouse / sneakers / tote bag / headband

#3 / Style With A Striped Tee & Longer Cardigan

How To Wear Leggings Over 50

Most of us own a striped tee and a cardigan, right? This combination looks great with jeans and is just as stylish when paired with leggings. To complete the look, add sneakers and a crossbody bag worn across your body for an upgraded take on the tee and cardigan pairing. You can choose the length of the cardigan you prefer; a longer one offers added backside coverage that some may appreciate. This casual look is perfect for running errands, and it’s a style that many women over 50 often shy away from. You'll feel confident wearing this outfit and show that such styles and outfits are absolutely appropriate for your age.

#4 / Style With A Basic Crewneck Sweatshirt

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Here’s how to make a sweatshirt look chic! Who would have thought that this "throw-on" style could feel and look so good? Adding a basic white crewneck tee underneath gives it a more polished appearance, making it seem like you put thought into your outfit rather than just throwing on a sweatshirt

Your hairstyle also plays a major role in how your look comes across, so taking the time to style your hair in a way that complements your outfit can really bring everything together. A sleek low bun is trendy and can elevate your look, especially since many tend to shy away from this hairstyle. Don’t be one of them! Finally, incorporating jewelry can help polish off the overall look.

Complete the look: tote bag / sneakers

#5 / Skip The Sporty Look

How To Wear Leggings Over 50

Wearing leggings doesn't mean you have to go for a sporty look; you can also achieve a casual, everyday leisure look! To do this, skip the sneakers and choose flats, like these loafer mules, instead. Pair your leggings with a chambray shirt and a sweater tied around your shoulders to create a more relaxed vibe rather than an athletic one. Taking a few minutes to style your hair in a half-up, half-down look with accessories will complete this outfit. You can easily replace your usual errand attire with this stylish alternative!

Complete the look: handbag / hair clip

#6 / Chic in All Black and Denim

How To Wear Leggings Over 50

This is a relaxed take on an all-black look featuring a denim layer—sleek, stylish, and very on-trend while still being age-appropriate. You can choose either a fitted or looser black tank top (or T-shirt), and the additional layer adds a touch of comfort; however, if you prefer, you can skip it altogether! Complete the outfit with a chic pair of sneakers and your everyday tote bag.

#7 / Super Laid-Back

How To Wear Leggings Over 50

You can wear a basic tee and leggings without looking sloppy! The key to achieving a polished look lies in your accessories and finishing touches. Adding jewelry, carrying a stylish bag, wearing a chic pair of shoes, and a well-styled hairstyle can elevate your outfit. Alternatively, you can wear a baseball cap for a more casual vibe. Combining these elements helps you avoid a frumpy appearance.

#8 / Keep It Simple With A Sweater

How To Wear Leggings Over 50

Here's another easy outfit idea: pair your favorite sweater—whether it's a crewneck, V-neck, fitted, or looser fit—with simple yet stylish pieces. This is a quick and effortless way to create a polished look. To enhance your outfit, make sure to choose the right jewelry, hairstyle, bag, and sneakers to achieve a refined appearance rather than a sloppy one.

#9 / Tailored With A Blazer

How To Wear Leggings Over 50

One of the quickest ways to enhance any outfit is by adding a polished layer like a blazer. This can instantly elevate a basic tank top or t-shirt paired with leggings. Blazers don’t always have to be worn formally; they make excellent layering pieces for relaxed styles, such as leggings.

Complete look: sneakers / handbag (investment item)

Don't be surprised if you start receiving compliments from other women while you're out and about. You're showing that women over 50 can look great in this style! If you've been hesitant about wearing leggings, I hope this blog post has encouraged you to give them a try!

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