As I found out on my recemt trip to cold Europe, 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 a normal trouser. 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 loser 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 lose fitted leggings were worn at the recent Chanel prefall 2012 collection. All were combined with nice tunics and dresses that would suit many a women over 40, as it both comfortable to wear and looks flawless and stylish.

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 as Anja is demonstrating so fine in the images above and below. 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. Legging would just accentuate those and you would usually look nicer with straight leg or wide legged pants. However, you could wear leggings with some nice boots.
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. In general, your ideal garments to combine with leggings include:
- Tunics
- Short dresses
- Boots
- Longer asymetrical pieces
- Long cardigans
- Big wide sweaters
- Sweater dresses
What not to wear with leggings over 40
- Avoid any tops that are higher than mid thy
- Don’t wear tops that are too tight
- Avoid animal prints and disco fabrics.
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. Another length I like in warmer climates is just below the knee. If you are short though, mid calf and short leggings should be worn with caution as they will make you look smaller.
Which shoes to wear with leggings?
As you could see from the Chanel 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. It can be done, however, as Anja so nicely demonstrates in the pictures above. She is wearing high heels adorned with lovely shoe accessories, tall boots and small boots. All look equally great!
What about jeggings and skinny jeans?

For me the same rules that apply to leggings also apply to skinny jeans and 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. Of course some ladies will be able to pull off skinny jeans with shorter tops, but most women will look better and more stylish with longer ones. 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 skinnys.
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.
What do you think? Do you like wearing leggings and how do you usually wear them?





{ 27 comments… read them below or add one }
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.
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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
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.
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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!
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.
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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…
Very thorough and thoughtful! I am a fan of leggings and wear them all the time!
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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!!
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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. ^_^
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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.
Val
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.
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