7 Style Solutions: How to Wear Leggings Over 40, 50, or 60

Leggings. For a tiny little piece of the wardrobe, these little pants certainly have the power to carry a lot of controversy around them! Especially for women who have a bit more, ahem, life experience. They’re super comfortable and you probably have a few favorite pairs. But, if you’re asking the question about whether or not you can wear leggings when you are over 40, then the answer is a resounding “YES!”

The concern about leggings for women in their 40’s, 50’s, or even 60’s often has less to do with the actual garment and more to do with the way that it is worn. But do not fear. Not only are leggings allowed for women who are past 30, they can also look great if you know how to stylize them.

Here are some sensational ideas for getting the leggings “look” without stepping over those dreaded age-related boundaries:

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#1 Leggings with a Long Shirt
Legging styles
Image: lindawaldon.com

For a super summer look that can’t be beat, don a light colored pair of leggings topped with a long, flowy shirt in a pastel color. Make sure that the shirt is long enough to cover your backside and reach your thighs in order to keep things on the up-and-up. It’s even better if your shirt has pockets, making it much more functional (since leggings typically don’t have pockets!). If you feel a bit frumpy and need to add some definition to your shape, go ahead and add a complementary belt to accentuate your curves, but be sure not to buckle or tie it too tightly since the whole point of this look is free and flowing. To complete the summery look, add a cute pair of sandals, a chunky necklace, and a bright smile on your face.


#2 Leggings with Riding Boots

Image: Pinterest

Boots are the best! And there’s nothing better to pair them with than a great pair of classic leggings. Choose a simple chambray, cotton, or denim blouse or menswear shirt to place on the top. Or try a sweater for cooler days. But remember, that the feature of this outfit is definitely the boots, so go with a plain, dark-colored pair of leggings to create a slimming effect. Choose boots that just graze the knee or, for even more coverage, go with a pair of uber-cool suede boots that hit you just above the knee. These also work when wearing a shirt-dress, poncho, or tunic. Any way you choose it, riding boots are the ultimate accessory to dress up your favorite, comfy pair of leggings.

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#3 Leggings with a Long Sweater

A long sweater can be exactly what you need to pair with your favorite leggings, particularly for fall or winter season weather! Just make sure to choose a sweater that isn’t so bulky that it makes your silhouette look frumpy instead of shapely and feminine. A patterned sweater can add interest to the top of your body and keep the eye looking upwards, particularly if you prefer to feature the upper part of your body and keep the eyes off of your bum.

Try a belted cardigan to add definition to your waist and create an appealing shape. If you struggle with looking too “hippy”, then choose a sweater that is colorful near the face and darker near the bottom. Then match your legging color with the darker color of your sweater to keep the lines sleek and slimming. Add large earrings, a brightly colored handbag, and stylish short shoe-boots to complete the look.


#4 Leggings with a Poncho

Image: Pinterest / fabulousafter40.com

Bringing back some vibes from Native Americans, ponchos work great as a style saver to complement a comfortable pair of leggings. Ponchos work well because they have the look of a sweater and function of a jacket, but are a bit more flexible as they can be used as outerwear or worn indoors. When pairing with leggings, choose a poncho that is long enough to cover your rear-end and keep you looking modest. Just be sure that the shirt you choose to wear underneath also offers decent coverage in case you get warm and need to remove your poncho.

This look works best when put together with a plain pair of dark colored leggings, but feel free to accessorize with a kicky pair of brightly colored boots! Add a chunky necklace to draw the eye up toward your face, and a complementary pair of earrings. You’ll be ready for anything!

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#5 Leggings with a Shirt Dress

Image: Pinterest / 40plusstyle.com

Have a favorite summer dress that just feels a bit too short for your age or stage of life? (Or maybe you’d like to cover those little spidery veins while still rocking your super-cute shirt-dress?) Place that shorter summer dress on top of a pair of subtle-colored leggings and you’ll re-claim that dress with a slightly more casual flare. This works well for a simple, white cotton shirt-dress or a longer linen dress with rolled up sleeves. Denim and chambray shirt-dresses are also excellent for this look, even possibly pairing them with a slightly patterned legging.

Remember that the point of this look is to go casual, add coverage, and create whimsy. Along the lines of accessories, add a summer hat (with a splash of color!), handbag, a pair of sandals or cute sneakers, and the ever-necessary pair of trendy sunglasses to finish off the super fun style.


#6 Leggings with a Maxi Dress

Image: thefabjourney.com

Not just for young girls to wear on the beach, Maxi Dresses with long slits can be the perfect summer item to pair with your favorite white or light colored leggings. Choose a sleeveless maxi dress (the strapless versions or spaghetti straps may be a bit on the un-supportive side and are best left to under-30s) or add a cute colored short-sleeved tee underneath if you’re not excited about baring so much of your arms. Try a bold stripe or Hawaiian print to create interest. For a whimsical look, add a long necklace with a giant bauble on the end, plus a pair of large hoop earrings. This look is perfect for going out to a light lunch or for a walk along the sand. Don’t forget your cute summer sandals or light colored flats, and a light handbag to make it look perfect.


#7 Leggings with a Skirt

Image: Amazon.com

Along the same lines of wearing leggings with a shirt dress, try adding a pair of leggings underneath a skirt to create warmth and coverage without sacrificing your style. This works great when you find that super great skirt that you love, but you just can’t stand the idea of bearing your knees! Try a flowy floral skirt, whimsical tulle number, or even a frayed denim skirt depending on the trend you want to go for. With a floral skirt, add a denim jacket, a scarf, and a chunky necklace plus short shoe-boots or flats. For something dressier, add a black tee and black blazer on top of a blush-colored tulle skirt with black leggings to stay sophisticated while channeling your inner ballerina. Have fun with short skirts while keeping your level of modesty and appropriateness on point!

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