How to wear leggings over 40 – a complete guide with the best leggings and tops and shoes to wear with them
Leggings can be an extremely comfortable piece of clothing to wear throughout the year. Here are all the tips you need on how to wear leggings over 40.
Leggings are thicker than tights so they are nice and warm and give good coverage for your legs.
But how to wear leggings so they also look good? And which leggings should you buy?
In this updated article with new shopping options, I will give you lots of guidelines on how to wear leggings over 40, 50 and beyond and where you can buy the best leggings online.
You will also find a capsule wardrobe of the best leggings as well as tops, sweaters, coats, dresses, shoes and accessories to wear with them.
How to wear leggings so you look stylish?
Leggings are a great transitional option for fall as you can wear underneath dresses or tunics, meaning you can continue wearing your favorite summer dresses for longer.
In my opinion, you should not wear leggings like normal trousers.
I would not do that at any age, but it certainly does not look very classy when you are over 40.
As they reveal all curves of your legs, I feel it is much nicer to wear leggings as a supportive element for the rest of your clothes, rather than as a main garment.
What are the best leggings to buy?
You will want to make sure that your leggings are thick enough and have a good stretch, yet are still firm enough to give your legs a great shape.
For that reason, it’s wise to invest in a good pair.
Ponte leggings (a hybrid of leggings and pants) are also a good choice.
If you like even thicker leggings, you may consider jeggings or elasticated skinny jeans. I would steer clear of shiny or sheer leggings.
Kim (above) looks fabulous in myriad shades of blue.
Check out these similar leggings, striped dress and slip-on sneakers.
Leather or faux leather leggings are great for an edgier look and can be easily ‘softened’ with a silk tunic.
Some great brands for leggings include:
Zella – these look just as good for everyday or for a workout.
Zella live in leggings
Satina – these come several colors, have a high waist (so perfect for hiding your belly)
Satina high waisted leggings
Stella Carakasi – my personal favorite. I own their second nature capris and ready to wear leggings.
They are firm and high-wasted, thick but not too thick and they keep their color and stretch, wash after wash.
Second Nature capris – Ready to Wear leggings
NYDJ – well known for creating jeans for curves rather than for teenage girls, NYDJ also has a range of flattering leggings.
NYDJ denim leggings
Eileen Fisher – classic and timeless styles.
Eileen Fisher denim leggings
What to wear with leggings?
Leggings look best with longer tops and tunics. Short dresses can also look great with leggings.
So, if you do own a shorter dress that you have pushed to the back of your wardrobe, you could always try it with leggings.
Leggings work best when they act as a base for your other clothes. If you want to wear shorter tops I would recommend wearing jeans and other pants.
Find out some of top recommendation for jeans here
The best tunics to wear with leggings
Leggings look better with longer tops. You still want to make sure that you create enough structure in your outfit though.
You can do that through the right tunics and longer asymmetrical tops.
The latter especially create flattering vertical lines and add a bit of extra style to your look.
Larace tunic top – Anne Klein tunic shirt – Eileen Fisher asymmetrical tunic – City Chic asymmetrical top
Short dresses to wear over leggings
Instead of designated tunics you can also wear a short dress over your leggings.
An asymmetrical dress or draped dress will make a real statement.
Eileen fisher shift dress – Chelsea28 twist detail dress – Sam Edelman asymmetrical dress – Tommy Bahama wrap front dress
Karen (above) teams her leggings or opaque tights with a floral dress.
Recreate her look with these similar leggings, printed dress and booties.
wear leggings with a long shirt
Because a long shirt covers up your bottom and thighs, you can afford to go a little bit edgy with your leggings. You could opt for a pair in leather or faux leather.
All of these shirts would look great with a pair of faux leather or coated leggings.
Rails shirtdress – Stella Carakasi tunic – Stella Carakasi white shirt – Alex Mill tunic shirt
Layer your leggings with a poncho or cardigan
Leggings are definitely your friend when it comes to layering.
They look great worn under long tops and ponchos with ankle booties.
If you’re heading out for a walk or to run errands, slinging a lightweight coat over a pair of leggings, together with a long-line tunic, can be a stylish option.
Halogen cashmere poncho – Madewell poncho – Line wool & alpaca blend cardigan – Cotton Emporium plaid sweater coat
Kylie (above) teams her leggings with soft pink and gray.
There is more inspiration here in how to wear gray.
Copy her look with these similar leggings, chiffon dress, cardigan and booties.
Combine your leggings with a long sweater
As you are likely to be heading into cooler weather, how about teaming your leggings with a cozy knit?
When choosing a sweater to go with your leggings, opt for a long-line version which will cover up your bottom.
If that is an area of your body you are confident about, you could always wear a pair of skinny jeans and a shorter sweater.
Halogen oversized tunic sweater – Eileen Fisher bateau neck sweater – Love by Design v-neck tunic sweater – Halogen oversized turtleneck sweater
Judith (above)
Get these similar long sweater tunic, leggings and boots to steal her look.
Leggings look great with jackets and long coats
Long cardigans can create lovely vertical lines which can help to elongate your figure.
But you can always wear a longer coat to keep you warm. How lovely would the plaid jacket look with a sweater, leggings and booties?
Another idea is to wear a longer top or short dress over your leggings and then to layer a moto or denim jacket over it.
Blank NYC moto jacket –1901 denim jacket – Kendall + Kylie plaid coat – Anne Klein drape front long jacket
Abi (above) wears a fabulous pair of faux leather leggings.
Check out these similar faux leather leggings, plaid coat and high cut sneakers.
In general, your ideal garments to combine with leggings include:TunicsAsymmetric tops and tunicsShort dressesKnit dressesLong knitted sweatersLonger asymmetrical piecesLong cardigansBig wide sweatersSweater dressesShoes to wear with leggings
As you will see from all the example in this article you can wear a variety of shoes with your leggings.
I feel that open vamp shoes look the best as they will further lengthen your leg line.
But, with cooler weather, you can definitely wear your leggings with closed toe versions such as booties, sneakers and knee-high boots.
Dolce Vita bootie – Very Volatile knee high boot – JSlides sneaker – Vince Camuto sandal
Sandra (above) wears her leggings / skinnies with a shearling coat and matching booties.
Get these similar leggings, shearling trim jacket and booties to recreate her look.
Accessories to wear with leggings
Of course, anything goes when you are choosing accessories to wear with your leggings.
But generally, leggings invite a casual look, so you could opt for scarves and crossbody bags rather than anything too formal.
Frye leather bag – Stella + Ruby tassel necklace – Halogen pendant necklace – Antik Kraft suede bag – Volcom pompom beanie – Madewell stack earrings – Halogen leopard scarf
Catherine (above) perfectly teams her leggings and tunic with a matching scarf.
Steal her look with these similar leggings, long tunic top, booties and scarf.
A capsule wardrobe of 9 ways to wear your leggings
Of course, there are so many ways you could put together the leggings, tops, sweaters, dresses, shoes and accessories to create many, many outfits. But here are 9 outfits to get your started.
For which body type would leggings be suitable?
If you follow some of the guidelines below, all body types will be able to wear leggings.
If you have very thick calves though I would recommend you wear skinny jeans though so the pants skim over your calves and will make them look slimmer.
Wide legged pants are also an option or you could wear leggings with nice knee-high boots.
Leggings can work especially well for the apple body type.
Your long tunic or top covers your belly and the leggings show off your fantastic legs.
You could never tell that Anja does have a tummy from these images (below).
Although women with the pear body shape can wear leggings as well, it is important that they choose a top with sufficient length over them.
How to wear leggings in summer and for travel
In case you are in warmer climes or heading on vacation, here are a few travel looks with leggings.
Deborah (above) wears a pair of crop leggings with a black tunic and Birkenstock sandals.
Check out these similar long tunic and leggings to cop her look.
Here is how I wore black and white leggings on a recent holiday. Tunic by Stella Carakasi (They also have a winter version).
White tunic over capri leggings.
Leggings with asymmetrical tunics
I especially love asymmetric tunics and tops as they create an interesting silhouette and lengthen you through additional vertical lines.
Julia (above) is winter ready with her asymmetrical tunic top paired with leggings.
Get these similar asymmetrical tunic, leggings, scarf and embroidered booties to cop her look.
Here is how I recently wore a super asymmetrical black top with white over the knee skinnies and a high / low tunic with very stretchy skinnies.
You can always find a great selection of tunics at Eileen Fisher and Stella Carakasi. In winter, layer these looks with sweaters and cardigans.
Bateau neck chiffon tunic – Silk tunic shirt – Wool tunic sweater
What not to wear with leggings over 40Avoid any tops that are higher than mid-thighDon’t wear tops that are too tightAvoid animal prints (unless you are opting for skinny jeans instead of leggings) and disco fabrics for your leggings and remember that the classier the top, the better leggings will look.The luxury fabric of silk, wool or cashmere will create a great contrast with the comfortable jersey leggings.What is the ideal length of your leggings
You can never go wrong with full-length leggings. These elongate and will make your legs appear longer.
Ankle-high leggings can also look sexy especially with heels or booties.
Hayley (above) opts for an ankle-high leggings to pair with sneakers and a long coat to give her body an elongated look.
Recreate her look with these similar bow blouse, leggings, coat and sneakers.
If you are short though, mid-calf and short leggings should be worn with caution as they will make you look smaller.
Here is a look with an asymmetrical tunic and draped leggings which are available in many colors.
Another length I like in warmer weather is just below the knee. These Second Nature Capri leggings from Stella Carakasi (below) are super fab.
Not too thin and very stretchy and comfortable. They are also great for tucking in your tummy.
I have these leggings in various colors and also use them for working out and yoga!
As you may have seen from the images above, it is great to wear a shoe in the same color as your leggings as it elongates your legs even further.
Clare (above) wears a pair of black leggings and lace-up boots.
Steal her look with these similar sweater, leggings and boots.
Tall flat boots can work really well with leggings, but short booties and ballet flats can work equally good.
I would not wear leggings with stilettos or very high boots over 40, unless you really know what you’re doing and you’re sure you’re not looking trashy.
For more info on what kind of shoes to wear with what pants check out this article.
What about jeggings and skinny jeans?
I’m also a big fan of looser fitting leggings, jeggings or skinny jeans.
Above is a look I wore to travel in. Also take a look at travel outfits for women over 40.
These will not show every curve in your legs, but will provide nice vertical lines and make your legs look long and slim.
Depending on the kind of jeggings and skinny jeans, your tops can be shorter for these pants although they will also look good with longer tops.
They can be a great asset for any wardrobe of women over 40.
Skinny jeans are usually a bit thicker and roomier so can be worn with shorter tops.
Be sure to wear the right underwear though, so there is no clear VPL (visible panty line). (Featured below are myself and Greetje).
Dayle (below) wears a black column outfit with a pair of skinny jeans and adds a pop of color with her scarf.
Check out these similar cardigan, jeans, boots and scarf.
Finally here is an overview in this short video!
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This concludes my guide on how to wear leggings.
I may add to this guide later as I discover new tips on how to wear them best, or have new photos to illustrate.
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I hope you got some more clarity on how to wear leggings! What do you think? Do you like wearing leggings and how do you usually wear leggings?
Continue reading:
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Feature image by Hayley
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