Leggings by Uniqlo

Leggings can be an extremely comfortable piece of clothing to wear throughout the year. 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.

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.

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:

What to wear with leggings

Leggings look best with longer tops and tunics. Short dresses can also look great 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.

Linen tunic | 40plusstyle.com

Long tunic to wear with leggings

Shirttail tunic | 40plusstyle.com

Long tunic to wear with leggings

Tunic and jeggings outfit | 40plusstyle.com

Stella Carakasi plaid tunicRebecca Minkoff silver bagNine West silver bootiesSimilar Liverpool jeggingsGorjana hoop earrings

Asymmetrical tunic to wear with leggings | 40plusstyle.com

Asymmetrical tunic to wear with leggings

I’m always a big fan of asymmetric tops and dresses as they create interest as well as long diagonal lines to disguise your belly. Both black and white can be a great base.

Asymmetrical tops and leggings | 40plusstyle.com

Gibson asymmetrical top – Stella Carakasi leggings – Superga ‘cotu’ sneakers – Karine Sultan chain necklace – Boden navy bag

Short dresses to wear over leggings

Instead of designated tunics you can also wear a short dress over your leggings.

A red dress makes a statement on its own. This versatile piece will look great with the right statement necklace. But it can also be worn over skinnies and leggings.

red dress by Eileen Fisher | 40plusstyle.com

Eileen Fisher dress

Here is another one that’s really good. You can wear this on its own or over your leggings. You may like to belt it to highlight your waist but can be worn loose too.

Shirtdress | 40plusstyle.comAll in Flavor crepe dress

Wearing a short dress over leggings

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 a pair in leather or faux leather.

Polo and leggings | 40plusstyle.com

Similar Spank leather leggingsPolo Ralph Lauren stripe blouse – Bernie Mev. bootie – Madewell burgundy tote – Rachel Comey square hoops

Layer your leggings with a poncho

Leggings are definitely your friend when it comes to layering. They look great worn under long tops and ponchos with ankle booties.Poncho, longsleeves and leggings | 40plusstyle.com

Eileen Fisher stretch leggingsHalogen cashmere ponchoBobeau rib longsleevesUrban Originals crossbody bag – Panacea tassel necklace – Marc Fisher LTD bootie

Combine your leggings with a long sweater

When choosing a sweater to go with your leggings, opt for a longline version which will cover up your bottom.Cardigans and leggings | 40plusstyle.com

J Brand ankle denim leggingsBobeau waterfall cardiganSole Society bootie – Madewell pocket tee – Antik Kraft satchel – Kendra Scott long necklace

Combine your leggins with a lightweight coat or cardigan

If you’re heading out for a walk or to run errands, slinging a lightweight coat over a pair of leggings, together with a longline tunic, can be a stylish option.Long cardigan and leggings | 40plusstyle.com

Lyssé high waist leggingsBernardo oversize coat1901 leopard print blouseVince Camuto bootieCult Gaia mini ark handbag

Leggings look great with a long straight cardigan

Long cardigans can create lovely vertical lines which can help to elongate your figure.

Long cardigan and leggings | 40plusstyle.com

Rag & Bone high waist leggings – Barefoot Dreams luxe cardiganHalogen turtleneck – Nordstrom crossbody bag Spring Step bootie – Baublebar earrings

In general, your ideal garments to combine with leggings include:

  • Tunics
  • Asymmetric tops and tunics
  • Short dresses
  • Knit dresses
  • Long knitted sweaters
  • Longer asymmetrical pieces
  • Long cardigans
  • Big wide sweaters
  • Sweater dresses

Here are a few more outfits to give you some inspiration for wearing leggings during fall and winter.

Outfit ideas on how to style leggings while layering | 40plusstyle.com

Outfit ideas on how to style leggings during winter | 40plusstyle.com

If you are heading into spring and summer, or going on vacation, then here is some inspiration for you.

Stylish outfit ideas on how to style leggings | 40plusstyle.com


Outfit ideas on how to style leggings | 40plusstyle.com

Shoes 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.

A ballerina shoe is a good option.

best shoes to wear with leggings: ballerinas


An asymmetrical shoe with an open vamp will make your leggings look extra stylish.Asymmetrical shoe with leggings | 40plusstyle.comAsymmetrical shoes

Finally pumps can be a great option too for your more dressy leggings looks with a long tunic. The Rockport total motion pointy pump is a popular option as Rockport’s shoes have lots of padding and are very comfortable. They comes in all kinds of colors and textures.

Rockport total motion pointy pump - a good shoe to wear with leggings | 40plusstyle.comRockport total motion pump

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.

What to wear with leggings | 40plusstyle.com

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.

Here are a few more travel looks with leggings.

wearing leggings over 40 while traveling | 40plusstyle.com

Here is how I wore black and white leggings on a recent holiday. Tunic by Stella Carakasi (They also have a winter version).

leggings and asymmetrical tops | 40plusstyle.com

Black tunic over capri leggings.

Chic leggings outfit | 40plusstyle.com

Styling looks with leggings | 40plusstyle.com

Leggings with asymmetrical tunics

I especially love asymmetric tunics and tops as they create an interesting silhouette and lengthen you through additional vertical lines. 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.

How to wear asymmetrical tops over 40 | 40plusstyle.com


Here are some more examples of women wearing asymmetrical tops and tunics over leggings. You can always find a great selection of tunics at Eileen Fisher and Stella Carakasi. In winter, layer these looks with sweaters and cardigans.

Eileen Fisher tunics

What not to wear with leggings over 40

  • Avoid any tops that are higher than mid-thigh
  • Don’t wear tops that are too tight
  • Avoid animal prints 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. 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.

How to wear leggings over 40 and be stylish | 40plusstyle.com

Another length I like in warmer weather is just below the knee. These Second Nature Capri leggings  from Stella Carakasi (below) are super fab.

knee high leggings

Not too thin and very stretchy and comfortable. They are also great for tucking in your tummy. Worn here with the printed Attitude is Everything tunic and the long camisole in serene.

hiding your belly with leggings | 40plusstyle.com

I have these leggings in various colors and also use them for working out and yoga!

Navy and white knee high leggings with buttons

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. 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?

how to wear skinny jeans over 40 | 40plusstyle.com

I’m also a big fan of looser fitting leggings, jeggings or skinny jeans. 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).

Stylish looks with leggings | 40plusstyle.com

Finally here is an overview in this short video!

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.

Stylish looks in winter with leggings | 40plusstyle.com

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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 them?

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How to wear leggings | 40plusstyle.com

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