How to wear leggings over 40, an extensive guide

by Sylvia

How to wear leggings over 40 |

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 do you wear leggings so they also look good?

In this updated article 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.

Guide and style tips on how to wear leggings over 40 |

How to wear leggings so you look stylish?

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 a main garment.

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.

Have a look at how loose fitted leggings were worn at Chanel a few years ago below. All were combined with nice tunics and dresses that would suit many women over 40, as they are both comfortable to wear while at the same time looking very stylish.

How to wear leggings over 40 |

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 you 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 |

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.

What garments work well with leggings?

Leggings are ideal to combine with tunics and short dresses. I often wear a short dress over pants but they would look equally nice over leggings. Leggings are also great contenders to wear with boots.

Below are a few combinations that would be great for spring, autumn or winter.

Outfit ideas on how to style leggings while layering |

Look 1: Spanx black leggings – Henwei belted cardigan – Anne Klein black v-neck top  – Lucky Brand Black bootie

Look 2: Bishop and Young beige and white poncho – Hue denim leggings in white – Joie cream turtleneck – B.P. bootie in taupe – Aiden rose gold necklace

Outfit ideas on how to style leggings during winter |

Look 1: Socialite gray sweater dress – Halogen leopard print booties – Sole society leopard print bag – Karen Kane leggings

Look 2: Liverpool blue denim leggings – Halogen black and gray cape – Karen Kane wrap top – Vince Camuto grey booties – Madewell gold necklace – Urban Originals gray handbag

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

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

Here are a few options for spring and summer:

Stylish outfit ideas on how to style leggings |

Look 1: Bardot drape dress – AG white leggings – Halogen white ankle strap sandals – Madewell Violet handbag – Nadri moonstone necklace

Look 2: Lush quail tunic – Eileen Fisher wrap – Natasha necklaceNina sandals

Look 3: Vince Camuto leaves tunic topSanctuary grease leggingsVince Camuto sandalsFrances Valentine bucket bagKarine Sultan gold necklace

Outfit ideas on how to style leggings |

Look 1: Rip curl kimono topNordstrom cropped leggings whiteDr. Scholls’ black sandalsAnna Beck earringsUrban Originals straw tote 

Look 2: Reiss olive tunicZella black leggingsTopshop embroidery bagNine West loafer

Look 3:Eileen Fisher top in Mimosa – Spanx leggingsPink Paradox London silver sandalsUrban silver toteKarina Sultan statement necklace in silver

Here are a few more travel looks with leggings.

wearing leggings over 40 while traveling |

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 |

Black tunic over capri leggings.

Chic leggings outfit |

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 |


Here are some more examples of women wearing asymmetrical tops 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.

How to wear tunics with leggins |

Eileen Fisher cowl neck tunicEileen Fisher sheer silk topEileen Fisher asymmetrical tunic

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 |

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

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

Which shoes to wear with leggings?

As you may have seen from the images above, it is great to wear a shoe in the same colour 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 |

Depending on the kind of jeggings and skinny jeans, your tops can be shorter for these pants although they will also look look 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 is myself and Greetje).

Which 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:

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.

If you want to make sure, you never miss an article and to get the best tips straight into your inbox as well as a free guide on how to find your style, be sure to subscribe to the weekly newsletter.

What do you think? Do you like wearing leggings and how do you usually wear them?

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How to wear leggings over 40 |


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{ 34 comments… read them below or add one }

Karen perrin

I disagree with some of the above – I’m 47 a freestyle snowboarder (I ride rails and big jumps) and a skateboarder. As well as having a successful career as an IT Architect. I wear leggings with my Vans tees and trainers all the time. I’m fit (I have to be, I compete), toned and healthy and they suit me. If you are still toned and have the figure to get away with it then why not? You shouldn’t have to cover up your thighs and hips with a big blouse or top if you don’t need to, just because you’re “over 40.” Age is just a number and shouldn’t be a barrier to what you wear if your figure is still good enough and it suits you. Great blog btw



I agree. I wear leggings with a sweater all the time, and sometimes with t shirts. Sometimes it covers, sometimes not. I don ‘t see the problem.



Totally agree Karen, if you are fit and look good why not indeed. However I think the article is talking generally, Id bet the vast majority of over 40s 50s are not snowboarders or indeed i assume would look good in leggings and regular size tees. I admire your fitness, I was a PT for over 20 years until fibromyalgia took a hold and now most days I can barely walk around the house, I still want to look good though lol but now comfort is a very close second.



Do you have any advice about wearing a Tulle midi skirt …I am 67 size 12 waist and would like to wear a black tulle skirt to a wedding…..if you had any guidance that would be great. The wedding is in Paris and is a black themed wedding.


Daphne Buckingham

This is my humble opinion. Leggings are too rugged for a tulle skirt, especially to a formal wedding. And if the wedding is in Paris, it’s safe to bet that it will be formal. Tulle is a delicate fabric, so should be worn with a delicate leg covering, such as sheer hosiery that does not “fight” the look. If it’s a midi skirt, then not much of the leg will be shown anyway. Secondly, if the wedding is in Paris, you need to be extremely confident about what you choose to wear. You don’t want to show up and feel like you are in costume. Parisian women have an effortless and elegant style. I say go for simplicity and put your effort toward a really good, elegant pair of shoes that will accentuate the skirt.


Linda Harris

I am short, and have short legs, so tunic tops make me look stubby. I’ve solved that by cutting off about 2 inches from the hem. A good length is to shorten to the tips of your fingers with your arm extended at your side.



Thank you for your tip, I am built like you lol and have terrible trouble buying clothes that fit and suit, I am 51 and 5ft and believe me every single lb shows up and is hard to loose. I am going to invest in a sewing machine and get snipping x


Lorraine Hill

Hello. All your advice seems to be for women who are short with apple or pear shapes. I’m exactly the opposite. 6ft and slim. I suppose your advice would be to do the opposite to what you advise. I love your advice though. Thanks



I give advice to women of all shapes. There is a special article for tall women too at


Donna Scanlon

Help this is a great article. I’m 68 and love wearing leggings with tunic tops. I would like to wear them with shorter knit dresses, but my slips are too long. Any suggestions for preventing knit dresses from clinging to knits. Should I just wear tights and buy some shorter slips if I can find them.




Why do you need a slip?
You don’t wear a slip with slacks or shorts or other legged bottoms.

Years ago women wore slips with dresses for modesty so you couldn’t see their legs and where they met (oh dear can I say crotch?)

Just use fabric softener for cling


Daphne Buckingham

Sometimes cling can be reduced by rubbing a fabric softener sheet onto the fabrics. As for slips, if you really need one, don’t bother trying to find short ones. Just use a good pair of sissors and cut the slip to the desired length. Presumably no one is going to see it anyway, and shouldn’t, so take care to select the right color for the garment being worn. A slip is just an extra layer and it should not bring any attention to itself.
In cold climates, a snug undergarment is good for thermal layering. Target has a long camisole (the length of a slip) that is available in the maternity department. It’s very stretchy as it fits close to the body. This may be a solution for you. It’s like a SPANX but it costs around $12.


ramani wittatchy

I like to wear leggings ,so im little short and how can I wearing shoes to ,if the leggings ower the ankle.?.High heels is good or not..I like to know from you..



Yes heels can work in a similar way as they are worn with skinnies. For lots more tips on what shoes to wear with what pants, see this article


Inaya Shujaat

Okay, you advised that people with big calves not wear form fitting leggings. What should we wear? You cannot, and should not exclude us. I see that you’ve been blessed with beautifully skinny legs. Good on you. What about the rest of us? I’m 41 years old, and I’ve never had skinny calves.



There are so many other options to wear. You could still wear skinny style pants but choose styles that skim the legs, not hug them. You may like to have a look at the body type guides in this section where I have written many articles for all kinds of body types.



I love your blog! Thank you for the tips with leggings. I wore them in the 1980’s and just started again. I forgot what I had been missing. So comfortable. Now I just have to find the right top 🙂



I am just turned 71, as I remember I wore a lot of leggings in 1966 , when I was in college. In fact I still kept some of them until now. Just last week, I tried them on and they fit !



My style sucks. I don’t know where to go.



There are over 1000 articles here to inspire you Robert. However for the most constructive help and personal feedback I recommend my 21 steps course or the 40+Style club where we practise style on a daily basis.



Fabulous article! Can you tell me when it was written? I appreciate dates on either articles or comments. Thank you.



This article is regularly updated with new looks and the latest shoppable items.



I love leggings and the assets shapewear ones in particular!
But my only gripe with them, is that because of the fact that most womens behinds are larger than their thighs, the material over the bum stretches and allows the skin and panties to be more visible than liked!!
My suggestion would be for the leggings to have a thicker knit ‘shorts’ area or failing that, to cover up the bum using a tunic type of top.
I love the versatility of these leggings, but think it very unsightly when walking behind a woman wearing these thinking, ‘does she not realise how see thru they are?? I don’t want to be stearing at a womans knickers, it should not be!!
So in short, make the bum area denser material, but the leggings themselves should be worn as women see fit!!! they are the best thing ever! just make sure you dont wear if frayed, faded or wrinkly!!! you’re welcome!! 😉



A grat pair of leggings which I wear almost exclusively know is Spanx…Coverage is really good and they hold you in. Comfortable, yet sleek.



Are flat knee high boots still in style with leggings?



That’s a classic style so can always be worn but shorter booties are more fashionable at the moment



I’m just trying to find out what are the best type of tunics to wear with leggings if my butt is large? I’m an apple shape, so my tummy is definitely large, but so is my booty. I’m also 5′ 4″. What can I wear that doesn’t make me look so fat?



You will want to choose tops that accentuate your slimmest pant. All wide is just going to make you look bigger so find tops that are a bit tailored in the waist. Empire tops can work too although it does not work for all apple women. I recommend visiting my article on the apple shape and my article on how to hide your belly for more specific tips


Lia Cooper

We like to style even as we age. This is very useful advice that’s going to help us look pretty.



I am in total agreement with your advice on how to wear leggings. I am in my mid 60s, am a full figured woman and I am tall. I absolutely love my leggings and find it hard to wear regular slacks now. Anyway, I would t think of wearing leggings/jeggings without pairing with a tunic length top…even if I were a skinny woman (like i used to be). Anyway, I have a good friend who is in her late 60s who wears leggings all the time. She’s a curvy girl and she is tall and in proportion. However, she NEVER wears longer tops with them and it’s rather embarrassing for me when we go out antiquing or whatever. She pairs leggings with short, fitted tees, etc. (Eww) I sure would like to tell her how inappropriate (and offensive) her look is but can’t bring myself to talk to her for fear of hurting her feelings. I sure wish she would wake up! She needs to read your article.



What you could do is just talk about your own experience and say something like “I found this wonderful website that has so many useful style tips. I found it so helpful. You may like it too”


Kammie Wilton

I have worn leggings since I was 6 years old.I feel comfortable and warm when I wear leggings.I wear leggings when I run and when I go to the pool.I feel happy and healthy when I wear leggings.



I have mixed feelings about leggings. I am petite and tops that just cover the butt or are asymmetrical look best. I need to show as much leg as possible. I rarely wear them outside the house except to exercise because they remind me of thick stockings, and I never wear them in our mhumid summers. I prefer slim pants.



I think leggings can be fantastic. If you wear it in the right way of course! It’s what they say: leggings are not trousers, don’t wear it like they are!


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