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 in winter or in cooler weather. 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 as well?

How to wear leggings so you look stylish?

In my opnion 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 or tight pants. These will not show every curve in your legs and provide nice vertical lines and make your legs looks nice and slim.

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

How to wear leggings over 40 chanel

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. It 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.

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.

I would not wear leggings if you have very big calfs. Leggings would just accentuate those and you would usually look nicer with straight leg or wide legged pants. However, you could wear leggings with nice knee-high boots.

What garments work well with leggings?

What to wear 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 winter.


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 more summer looks with leggings.


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 asymmetrial black top with white over the knee skinnies and a high / low tunic with very stretchy skinnies.


Here is how I wore black and white leggings on a recent holiday. Tunic by Stella Carakasi. Winter version here.

leggings (4 of 4)opt

Black tunic over capri leggings.

leggings (1 of 1)opt


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.


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; 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.


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.


Which shoes to wear with leggings?

As you could see 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.

What about jeggings and skinny jeans?

how to wear skinny jeans over 40

For me the same rules that apply to leggings also apply to jeggings. They can be a great asset for any wardrobe of over 40 women, but they usually look better when worn with longer pieces on top.

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). When your skinnies are very tight, many women will look better and more stylish with longer tops. As you may know I’m actually quite a fan of wearing dresses over pants, although I also do that with wide legged pants and not just over leggings and skinnies.

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 are also a good choice. If you like even thicker leggings, you may consider jeggings or elastic skinny jeans. I would steer clear of shiny or sheer leggings.

Leather or faux leather leggings are great for a more edgier look and can be easily ‘softened’ with a silk tunic.

Some great brands for leggings include:

Fore some leggings or great tunics to wear with them, here are some fabulous items currently available online.

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

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In general I think leggings are a good accessor, as long as they are under a dress or large blouse, but do not serve to replace “pants.” However, I prefer they be traditional colors and materials.

I think jeggings are an atrociously eye-assailing abomination and I cannot wait until they find their way into fashion’s dustbin of non-surviving trends. Harsh? Maybe.


Hi Konon. Thanks for your feedback. As long as jeggings are worn as described above (supportive garment), it’s ok. Otherwise, I agree with you!


I love leggings. I think when worn as you have noted, Syliva, with more generously long tops, they highlight the part of the leg that very rarely changes in size or shape as we age (the knee to the ankle). Highlighting the very feminine silhouette of the lower leg is very flattering, no matter what a woman’s size. Thanks for all of the great inspiration above. I love all the pics and I am actually surprised to find that I like the very top pics that feature the dresses with cream leggings – very chic!


Yes that’s right. Although in many cases I personally still prefer skinny pants that don’t completely ‘hug’ the calf…I still love to wear white and cream pants and find those Chanel combinations so chic as well!


I love leggings. I have a pair of black ones and a pair of brown ones. They are really heavy knit – hold their shape (never bag at the knee or in back no matter how many hours I wear them) and are very warm. I treat them like tights – if my top isn’t long enough to wear over tights then it isn’t long enough for my leggings. I like them to come to the top of my foot and I wear them with boots – ankle, to the knee, or over the knee. I would never want any skin to show between a shoe and a legging. I do not wear them when it gets warm. I also have 2 pair of denim leggings and I love those most of all but I apply the same rule as knit leggings. They look good with a more casual top. I am only 5′ tall and one trick I have learned is to wear black boots with black leggings and brown boots with brown leggings. This way, even if the boots are short, I get a longer leg line.


Yes, that’s a point I forget to mention. You definitely need to make sure that the leggings are thick enough to cover you legs and as you say, hold their shape. I can’t remember ever wearing leggings with a shoe and opening either, but I do think that Anja really pulls of this look with her (dancing) shoes, so it can be done!


Anja always looks wonderful! I appreciate her contributions to your blog. I don’t think tall girls have to worry about cutting off their leg line as much as short girls. 🙂 And I might even try her leggings and shoe look if I had thinner leggings – more like footless tights. Mine are too heavy to wear with anything but boots.


Yes it all comes down to dressing and doing what’s right for your body type 🙂


Women in other countries don’t seem to have this issue with their clothing. They just tend to not wear certain colors after a certain age. With regard to leggings specifically, I think most women can take excellent cues from the Indian and Pakistani clothing called ‘Salwar Kameez’. If you search online, you’ll see many of these pant suits are beautifully paired and colorful. Also, they are feminine. I think if a woman applies the same principles with regard to tunics and the shape of the pant suits, there won’t be any problems pairing an outfit together. I have yet to have anyone tell me I look horrid in one of my Salwar Kameez outfits. But, I have had someone tell me I look horrible in western clothing. Hence, I still am a bit blundered as to why we in European countries and the USA always have such a calamity with our styles. Mystery…

Heather Fonseca

Like you I believe that no one, NO ONE, should wear leggings as if they were pants. Well, it looks cute on little girls, but once you hit about 13 the look should be avoided. The leggings as pants look is very popular in LA at the moment and lots and lots of women are looking really terrible as a result. However, when worn light heavy weight tights under a tunic or short dress I think they’re great.
At one point I was also very against skinny jeans, but now that I have a pair I really love them. They give a lot more support than leggings and I think can look good with a regular top.


You know what? I don’t even like it on little girls! I really don’t understand why women would want to wear leggings like that. It’s not flattering at all. I do like skinny jeans as I wore them above with a large jumper (or similar). Unfortunately, I don’t own one. They are just too hot for Singapore!

Jeannie Heilman

Hey it is a free country and we wear what we want to wear.

Some like to cover their skin and many like to flaunt it. If you don’t like it then you don’t like it. Leggings are a hit and it is flattering to be in style.


I love wearing leggings with knee-high, flat boots and a long tunic-style top and/or cardigan, it’s a look that I find quite stylish and comfortable as well. As for skinny jeans I prefer them snug fitting but not too tight, and I’ll wear them with boots or ballerina flats and slightly longer tops, cardis or a blazer.


I would do the same for skinny jeans and not buy them too tight. Sounds like you look very stylish with leggings and skinny jeans indeed!


Very nice guide on how to where leggings. I too love wearing leggings and tight jeans especially right now with the colder weather. I pair it with short dresses, sweater dresses or long cardigans. Knee-high boots for sure. Love the look because it’s stylish and comfortable!


Thanks and welcome to 40plusstyle! Yes, they are great in cold weather. As I live in the tropics I don’t wear them so often…

The Style Crone

Very thorough and thoughtful! I am a fan of leggings and wear them all the time!


I know you are an expert at wearing them. It would be nice to feature some of your outfits in this post.


Great Post! I haven’t worn leggings for quite sometime…


Thanks Robert. Try it out sometime..


This are a piece of clothing (leggings,jeggings) that I have not tried that much yet. I have two skinny jeans and so liking it but still I am not really that confident. And you are right Sylvia short tops isn’t the best way to wear for this pieces of clothing. It shows some of those not good looking flabs, lol. So now I have to re-design my style especially if I am wearing skinny tights. Well sometimes I forget I am over 45 I thought I am in my 20’s hahaha!!


Yes I know that feeling. I too have to remind myself that I’m not 20 anymore. Sometimes I still feel like I am 😉


Not skinny tights, but skinny jeans. ^_^




I am a 70 year old women size 8 and still love fashion. I love dresses but have bad viens on my legs, so I wear pants or maxi dresses. Would it be ok to wear a slightly shorter dress lenght with leggins or would I look ridiculous! I also loke to wear a 21/2 inch heel
Would appreciate some help.


I think that would be totally ok and can look very chic! Wear with a nice tunic or dress. You could combine with ankle booties or shoes with a 2.5 inch heel. Thanks for your questions Valerie. Feel free to put images from you style up on the style forum. That is also a good place to ask more questions so I and others can help you.


Thanks Sylvia, I shall try dress up today .


Hello, I am wondering if it is ok to wear a tunic dress with brown leggings and brown clark knee high boots in May? I am going to a wedding rehearsal May 4th in California for my niece. But I am from the Seattle area. We wear boots here a bit longer in the spring because weather is cooler. But didn’t know if it is a fashion no no to wear the boots in a little warmer weather. Long beach area. I am 49 and the outfit is very age appropriate and have gotten complements on it. Just not sure and don’t want to embarass my niece. Thank you for your help.


Hi Liz, I think that you can wear boots in cooler weather all the time. I’m just not sure if they would be the best choice for a wedding. But then you are saying that it is a wedding rehearsal so that should probably be fine. For the real wedding I would try to wear dressier shoes and I would stay away from leggings too.


Thank you Sylvia for your response. It is appreciated. As it turned out it was fairly warm so I wore sandals with the outfit and it looked just fine. Yes I agree about legging and weddings. I wore a flowery, flowing spring colored dress and some black ankle strap sandals. I found out that boots are often wore almost year around there in Long Beach area. Thanks you again for your input. Liz


I am 70 and tried on leggings today. They are so comfortable! I have a calf length winter coat. Thought my short boots looked funny, so bought long boots. Now my wide bottom jeans don’t work. That’s how I came to try on leggings. Looks great as long as I don’t take my coat off. Next purchase…….tunic length cardigan or sweater dress. Thanks for the great advice.


Thanks Maisie. Yes, longer cardigans and tunics are definitely the way to go with leggings. Hope you find something nice and I hope you can share your looks with us on the style forum!


I am 62 and I got a pair of leggings from a friend for my birthday. She said I should wear them to my yoga classes but I am concerned about wearing them out in public at my age. I love how comfy they are but the material is not much thicker then a pair of opaque tights. I been wearing them around the house but need some opinions on whether I should wear them out.


I would not wear them if they are see through, but other than that leggings for yoga are ok. If see through, then only wear them as you would tights. You are never too old to wear normal leggings for your normal clothes, but I would never wear them without a long tunic or short dress over them.


I don’t think anyone should wear leggings as regular pants, don’t care what shape your in. I wear them with a tunic and booties or high boots and feel great. Any top should fall below the butt area. I’m 58 a size 4 and exercise-so I feel pretty confident when I wear leggings.


I am over 60 and love leggins, but have trouble finding things to wear with them…longer tunics, etc. Can you give me some advice? Thanks.


I often wear short dresses over leggings instead of tunics. There are no special places to find them but you can see them everywhere. Just go for a style that suits you. Hit the stores perhaps wearing your leggings, and try a few! If you through all my outfits in the what i wore section, you can see many of my own examples. Although I don’t wear leggings so often, I often wear dresses over pants, which is similar.


The BEST leggings for anyone over 40 (I’m 56) are Eileen Fisher’s skirted leggings. The fabric is very high quality and a nice thickness. The miniskirt is attached so you don’t have to go searching for the right layering piece. The hems are fully finished–not raw edged like a lot of cheap leggings. If you have a large bum or jello thighs, this covers them elegantly and effortlessly, and for all of us, you don’t ever have to worry about cling around the crotch. All the comfort and styling without the mess!


I am over 40, petite, fit and Asian, but I am always told I look like I’m in my 30’s.
I feel that some things like wearing short skirts (not minis) I am able to get away with.
I do like solid colors and more fitted dresses and tops. But the area I have difficulties with are dressing to look my age but more in a hip & sophisticated fun way. As I am single, I would still like to dress to impress. Any advice?


I believe it immediately that you look a lot younger. So many Asians do; I can never guess the age of an Asian woman. My site is dedicated to this topic so you will find articles throughout this site that tackle it. All the clothes I feature are in my opinion young and hip. I would say to trust your instinct. If you look in the mirror and it feels good to you, then it is.

J. Rae

I am a 42 year old woman who happens to be African American. I am fit, (a size 2) and look like I am about 29… I still get carded at the liquor store. I absolutely love leggings and skinny jeans because I have a dancers body and they look great on me (I’m a yoga teacher). I realize maybe I shouldn’t ever wear leggings as a main garment but as a yoga instructor I find myself doing this often (no complaints ever)! I would like to know how I can maintain my style without looking too young. While I prefer to look 29 vs 42 whatever 42 may look like, being stylish and chic is important to me. I also have trouble finding clothes sometimes because of my body type. I’m long and lean with a very small waist (size 2) but my butt and hips are big in a sense considering my waist. So pants are usually tough. I have a size 2 waist and a size 4 butt like a tiny Kim Kardashian). That is why I love my leggings and yoga pants. HELP!!


Hi J. We are all different so I can’t judge from this comment how you look in your leggings. If you like to show both your waist and butt they sound like a good option. you may also like to experiment with wearing a tunic or dress over leggings (or pants) as has been featured on this site many times, which would solve the size issue and which I find a very classy look for women over 40. You could consider uploading your photos to the style forum so we can all have a look and give you more detailed advice.


Leggings question: I have several solid and patterned dresses that would work well for fall if I paired them with leggings. However, one colleague suggested that my dresses are too long (fall just below the knee, since i am petite) to wear with leggings. Any suggestions? Should I consider having the dresses hemmed to just above the knee?


Yes dresses over pants and leggings usually look nicer when the dress is a bit shorter. That is usually how I wear the look (check the what I wore section for lots of examples). You want to aim for the nicest silhouette which often relates to the 1/3-2/3 rule (explained in my style course). For more ideas on how to dress the best when you are petite you can also check this article:


Thank you so much for this write up on the leggings! The entire sites subject is exactly what I was looking for! I turned 40 last March and I have been struggling with how to dress. I have two teen daughters that dress so fashionably and I didn’t want to become the Mom that dressed frumpy! I was especially leery of leggings at my age and your article has made me so much more comfortable to wear them. I constantly preach to my daughters that leggings aren’t pants! I guess I just felt like I was supposed to dress like my mom did when she was 40 but after reading your posts I realize I can still dress fashionably without dressing too young for my age. Thank you again! I’m off to buy some leggings!


You sure can Stephany. Welcome to 40+Style!


I’m 61. 25 years ago I enjoyed wearing stirrup stretch pants. They were like leggings but not the skinnies type. They did form fit to the leg but rather had a smooth vertical look and did not hug the knee. I would kill for a pair now. I had a great pair of black one when micro fiber first came out. Alas, they had a tear in them from being worn out and I have never been able to find another pair. Does anyone know if they still exist?


Thanks for great advice on leggings for the over 40s-50s etc. I’m going to a nephew’s 21st party, and smart casual is of course the dress code. Don’t want to look like an absolute dag (Australian for “dork”?). Was going to wear a jersey red dress – but thought this would be too dressed-up. After reading this piece, have decided on a shorter red tunic dress (above knee length), and loose fitting black leggings/pants. A perfectly comfortable outfit. Thanks for providing the lowdown, and such great visuals of examples.


Sounds like the perfect outfit for the occasion Carmen. Great to read that this article inspired you!


hi there, thank you for your wonderful website & advice!! question: how do i transition my substantial black leggings & tights (dkny, lysee and spanx) that i wear with above the knee knit shifts and shirt dresses, into a spring and summer look? most of my dresses are 3-4 season ones that are knits in various shades of solid blues and also black and berry. i also have a few short jersey shirtdresses with embroidery on the front (navy and gray backgrounds). i am currently wearing short black suede boots with the black leggings & tights. my daughters look great in black leggings and ballet flats, which is a wonderful look, but my daughters are young! i am in my early 50’s! can i keep the black leggings for the spring & summer? should i consider navy leggings? what shoes should i wear? thank you for any helpful advice! i am in the nyc area, thank you again!!


You can wear your leggings with summery jersey dresses. This is especially nice when you select a great print. Another option is to choose a cotton short dress in a light color, like this breezy white dress You can also consider getting some white leggings and combine with a long cotton blouse or short dress as seen here I think ballet flats can work really well with leggings as can some funky sandals. You can definitely consider navy which is a bit softer than black and can look really great with lots of colors.


Hi Sylvia,

Thank you for the wonderful suggestions! I thought it was a fashion faux pas to wear the black leggings with the lighter short dresses! I’m going to try some light-colored short dresses with my leggings, and I now have the courage to try some white leggings for the 1st time. (I like the outfits in your pics)……again, many many thanks!!


I love the leggings and short dress look for both winter and summer. Is a dress over leggings still in vogue in your summer this year? Its winter here in NZ but I really want to be able to wear my capri leggings with my short dress/tunic for this coming summer. Please advise?


Absolutely. I still wearing it frequently. Although usually with skinnies rather than leggings

Cynthia M

Just found your blog via Pinterest – hooray! A reasonable voice in a sea of extremes! I love leggings, and wear them all year, usually with a fingertip-length tunic. Sewing is a passion, and I use a lot of chiffon and velvets in my tops. Some of the photos above seem like the tops/dresses are too long for leggings. I’m also in the process of losing weight, and leggings can be worn over a large range of sizes – gotta love stretch fabrics! Here in Texas, a tunic, leggings, and cowboy boots are typical. Again, thank you for the blog!


Welcome Cynthia. Great to see you found your way to this website. Lots of articles to explore! There is one on Texas as well where I was indeed wearing leggings!

Cathy Harvey

Leggings look utterly ridiculous on anyone over 40. I’m sorry. It’s simply the unvarnished truth.


It may be your truth Cathy but it’s certainly not mine. When worn right, they can look really good.

sheila meadows

My long time girl friend who was a buyer for Marshall Fields just got me onto leggings. We are both in our 70’s and I was shocked because of our age but having just bought a couple of pairs of leggins, SIMPLY LOVE THEM. I am in Florida and worn with a lovely summery top, look fantastic. SO PLEASED I TOOK HER ADVICE.


Wonderful to see that you found leggings that worked for you. Enjoy!


I agree Sylvia. My mother is 83, and looks wonderful in loose fitting leggings. And, now she’s sporting the latest summer look “legging” (we’re in Australia) – being the non-stretch rayon harem pants style. That is, the style that’s gathered at the ankle. In paisley and other very flattering prints, they look great . . . and I imagine are as comfortable as wearing pyjamas – only they look nothing like pyjamas. Which is the comfort standard I always strive for.

Sabina @Oceanblue Style

I like either way short or longer tops. Usually that would be a coat. But wear mine with moto jacket, fake fury vest and V-neck sweater as well like here…

Have a great day Silvia! xo Sabina


I have black leggings but when I wear them they are somewhat wrinkley looking or slightly bagging when getting up from sitting around knee area. Should I invest in more tightly fitting “tights”? I plan on wearing skirts and tunic length tops on a cruise but w/o bare legs. I’m a fashionable 72 year old. Thank you


Good quality leggings can make a difference to your look, so I think it’s worthwhile investing in a good pair. Welcome to 40+Style Ann and enjoy your cruise!

Sabina @Oceanblue Style

Totally agree with you Sylvia. Was just thinking the same thing. I keep coming back to this post because leggings can be so stylish and material mix can make a difference too. So love your advice here!

Sabina @Oceanblue Style

Totally love my Adidas animal print grey leggings and have been wering them for 2 years now. Great for sightseeing in NYC (see current post) or everyday life. I just dont feel that comfortable wearing them the Chanel-style. Love the pics here Silvia though. But not for me. Makes me feel hidden. Have a nice day! Sabina @Oceanblue Style


“Jeggings” (woven fabric leggings) are my absolute wardrobe staple. I have them in very many colors and designs … even in pastels (yes ;-). They are so flattering for “inverted triangle” types, putting more volume around the legs, in order to balance a big bust and broad shoulders. That’s also why they cannot be “flashy” enough! (I though do not like animal prints, except zebra, so this is not an issue for me). I had already started wearing skinny jeans and pants as soon as they made their comeback by 2005, mostly with short dresses. And “jeggings” do the same job … a lot cheaper, with flashier designs and more comfortable. Nowadays, I would kind of feel “naked” in a dress with tighs only.
I even wear black “jeggings” for (easy) business occasions with a white shirt and a long black boyfriend blazer (long defined legs seem to make up for the “not recommended” not fitted blazer ;-).
When it comes to shoes, to my opinion, everything goes but low sneakers (which make me look as heading straight to the gym, though high sneakers are ok). I even don’t hesitate to pair black “jeggings” with black high (block) heels, bright colors rather with beige or white shoes (stilettos are not for me, anyway).
That’s where sufficient length becomes important, and to me the only downside of “jeggings” is the following: it’s quite hard to find them long enough without them being too wide, slipping and getting quickly baggy around the knees. Therefore some of my “jeggings” are in smaller sizes and I wear them with booties, or colored/striped long socks.


really a great post.

Age is not a factor to affect your looks, if you carry off what you wear with confidence. Belief in yourself is the key to fashion in the slightly higher age bracket.


I am in a wheelchair and age 62. My legs are ugly and I have poor circulation so I have to wear support socks or hose. So I always wear pants. My daughter is getting married in the fall and I have a off white vintage type tunic with a small gold embellishment between the breast (she picked it out) and plum color leggings. My question is, I want to dress it up a bit so I bought some gold flats (I can’t wear heels) with rhinestones and gold embellishments at the toe. Should I keep the flats or try to find something in the leggings color to match. Any other suggestions would help. Thank you so much.


These sound like a great choice! Congratulations and have fun at the wedding.

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