What shoes to wear with leggings in the fall

How to wear leggings over 40 | 40plusstyle.com

An update to an old favorite!

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 opinion you should not wear leggings like normal trousers. I would not do that what shoes to wear with leggings in the fall 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 a few years ago 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.


How to wear leggings for winter | 40plusstyle.comLong tops and ponchos with leggings | 40plusstyle.com

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

How to wear leggings | 40plusstyle.comHow to wear asymmetrical tops with leggings | 40plusstyle.com

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 asymmetrical 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 (They also have a winter version).

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 wear 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. 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

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:

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

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?

This article contains affiliate links.

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What shoes to wear with leggings in the fall

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What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


What shoes to wear with leggings in the fall


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