How to Wear Leggings

How to Wear Leggings

A while back, my good friend Grace wrote a fabulous post called Fashion Over 50. She received a great response in the comments and that post consistently gets great traffic. Evidently there are a lot of women over 50 searching for fashion advice! I’ve been begging her to write more style posts for me, and she finally agreed to share her fashion advice on how to wear leggings.

I’ve been wanting to add leggings to my wardrobe, but I’m always a bit unsure how they will translate, and yet Grace always wears them with panache! So without further ado, I give you Grace!

How to Wear Leggings

ski pants

from Poppy Gall Design Studio

Leggings have been around since I was a little girl in the 60’s. The stretchy pants, with the help of newly popularized synthetic yarns, migrated from the ski slopes to every day wear. Young women wore them as they danced to 45s with their girlfriends on shag carpets. And 50 years later, they’re still here. Is it no wonder? Is there anything more comfortable?

Think you can’t wear leggings at your age? I wear them! Here are the rules I follow. Leggings are worn in 3 general ways:

Leggings as Tights

Since “hose” has become a 4-lettered word, leggings are a good way to have some modesty when the situation calls for it. Wear leggings with a dress — to the knee in the summer, or to the ankles in cooler weather with boots, pumps or ballet flats.

Leggings as Pants

Just Say No. Really. Awhile ago, I saw a beautiful woman with an amazing physique wearing leggings as pants. Meaning, she had on a top that one would wear with jeans or slacks. I saw her every nook and cranny and muscle structure. It made me blush. For her.

Leggings as…Leggings

This is what we’re interested in today. And there are just THREE major rules:

3 Rules for How to Wear Leggings

#1. Fabric and Fit. Make sure the fabric is heavy enough and stretchy enough. There may be some trial-and-error, but it’s really Rule Numero Uno. You don’t want your skin to show through, nor your lumps and bumps to be visible. I bought one pair that didn’t have enough Lycra and I had the proverbial “elephant knees” by the middle of the day. I’ve had good luck with the Simply Vera Vera Wang leggings at Kohl’s.

#2. Cover your Crotch. I hate to be so crass, but – there you have it: I can’t say it any other way. Wear leggings with tunic tops that will cover you front and back, and won’t cling if you walk or sit.

#3. Find tops that will give you a graceful proportion; not voluminous, and not tight to your body.

Check out these three outfits I put together, from casual to dressy:



All three tunic tops above flow away a bit from your belly and hips to give you a graceful, and tasteful, silhouette. Aside from white in the summer, stick with very dark colors from black, to brown, forest and navy. Try subtle patterns, too!

Here are some NOT to wear, and I’ll explain why:

how NOT to wear leggings


How NOT to Wear Leggings

From left:

  • Don’t hide behind volume if you’re worried about your figure.  It’ll make you look bigger and top-heavy. And don’t wear matchy-matchy frumpy shoes.
  • Don’t use a too-short dress as a tunic. Don’t wear gaudy leggings. And don’t try to look like a little girl.
  • Don’t wear a body-hugging top. Even if you have a nice figure. And goodness, please don’t wear stiletto pumps. [Does “hootchy-mama” mean anything to you?]
  • Don’t wear a jacket; it’ll just look like you forgot your pants. Did I say not to wear stiletto pumps?

Leggings In Real Life

Here’s moi with some of my favorite leggings outfits:



Want to see more legging outfits?

how to wear leggings

how to wear leggings casual


So whatever your size, style or season, go for it!

How to Wear Leggings

Where To Buy:

We used Polyvore to put together these outfits. Some of the pieces are available to purchase, but not all. I’ll list what I can!

From Fashion Over 50 – How to Wear Leggings:

From Fashion Over 50 -Leggings – Dressy (unfortunately most of those tunics are from European stores):

From Fashion Over 50 – Leggings – Casual:

From last set (Legging Styles):

So there you have it. Are you ready to go out and rock the leggings!??

For more fashion inspiration for women over 40, check out all of my Fashion posts. Or better yet, sign up to be emailed my weekly fashion & beauty digest with a recap of the week’s fashion & beauty posts.


  1. MLingle says

    Nice post! Enjoyed the “Leggings in Real Life.”
    I hate shopping so I loved that you listed stores and brands names.
    I might actually enjoy going to a store and searching out some of the pieces you mentioned.

  2. Aisling says

    Brilliant post and also very entertaining – Love your writing style! I wish more people would take your advice however, particularly the ‘Leggings as trousers’ part! Also, just read your post linked to above. The comments are so true, this advice is for a very broad age range. Looking forward to seeing more posts from you!

  3. Heidi says

    I hate when people do not “cover their crotch”!!! With that said I still would not feel comfortable wearing them at all…love the look but too awkward for me personally. As always you look amazing :)

  4. Mama Obito says

    I would say this is the answer to my doubts in wearing legging, considering my pear shape. Thank’s for sharing! Will bookmark this page.

    • Grace says

      Mama Obito,
      I’m so glad!! Wear a bright scarf that is flattering to your skin tone, or a big bold necklace to draw the eye up. I’ve become an apple and I find this trick is helpful!

  5. Tammy says

    I am 51 and I LOVE leggings! I am always in doubt about what looks too young for me to wear. You have helped me alleviate that fear. You look awesome! And THANK YOU for showing how NOT to wear leggings. So many people wear them as pants and it is just WRONG! I don’t care how young or how skinny you are, you should cover your crotch and your hiney!

  6. Lisa says

    I’ve been unsuccessfully trying to convince my 17 yr old that just because they put 2 gold fake zippers on the front for pretend pockets, it does NOT make them pants! I’ll be showing her your article and hope she takes advice from am outside perspective! She tries to wear them with fitted shirts that end at the waist and black military-ish style boots with fur around the edges. She claims the kids at school compliment her on it!!! I love my leggings and love so many of your points and tips. Thank you!

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