How to Wear Leggings

Fashion Over 50: How to Wear LeggingsA 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.

So without further ado, I give you Grace!

How to Wear Leggings

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. A while 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 Wearing Leggings for Women Over 40

#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. We highly recommend the Hue Ultra Wide Waistband Leggings at Nordstrom (make sure you click on the Regular sizes if that’s your size; for some reason this link defaults to the Plus sizes.) They’re regularly $36 and often go on sale for 25% off, bringing them down to $27. You can’t beat the value.

#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.

how to wear leggingscowl neck tunic // green blouse // zip seam tunic sweater // Hue leggings
brown riding boots // black dress boots // suede tall boots
earrings // cuff bracelet // crossbody // layered necklace // scarf // pave cuff // black tote

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

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 Grace with some of her favorite leggings outfits:

Fashion Advice for Women Over 50: How to Wear Leggings

Fashion Advice for Women Over 50: How to Wear Leggings

And here are some of Jo-Lynne’s favorites.

#1. With a tunic sweater and riding boots:

Fashion Advice for Women Over 40: How to Wear Leggings with a Tunic Sweater

tunic sweaters // Hue Ultra Wide Waistband Leggings // similar riding boots

#2. With a chambray tunic, infinity scarf, and OTK boots:

Fashion Advice for Women Over 40: How to Wear Leggings with Over the Knee Boots

chambray tunic // leopard infinity scarves // over the knee boots // Hue leggings

#3. With a tunic blouse and riding boots:

Fashion Advice for Women Over 40: How to Wear Leggings with a Tunic Blouse

roll tab sleeve tunic // Hue leggings // similar riding boots

#4. With UGGs and an extra-long tee under a drapey waterfall cardigan:

Fashion Advice for Women Over 40: Casual Outfit with Leggings

waterfall cardigans // long tee // Hue Ultra Wide Waistband Leggings // UGG Classic Cardy

#5. With a sweater dress, riding boots, and a scarf.

Fashion Advice for Women Over 40: How to Wear Legging with a Sweater Dress

sweater dresses // floral scarves // Hue Ultra Wide Waistband Leggings // similar riding boots

So whatever your size, style or season, go for it! Are you ready to rock the leggings!?!

Fashion for Women Over 40: How to Wear Leggings

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45 Responses

    1. I love your tips on how to wear leggings but how about the printed leggings? Are those appropriate for women over 40?

      1. Thanks! I love the printed leggings, despite what I said in the post. When I wrote it, there weren’t a lot of options, but lately I’ve found many I like!

      1. They are great! Especially in a wet NW Winter. They are thick enough to hid perfections and come in a variety of jewel tones for pops of color!

  1. 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. 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. 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. 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.

    1. 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. 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. 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!

  7. LOVE the article! I am 65 and a plus size. This article is very helpful. I just got a pattern to make leggings for free on Facebook ( I am in no way afilliated, but just want to pass on the goodness.) They can be made in 30-60 minutes and are a great beginner project. How do I know? I taught my daughter how to sew a pair on Saturday! Go to Patterns for Pirates PDF and ask about the free PegLeg pattern.

  8. YES! thank you ladies for this post. I am in my early 40’s and love the look of leggings with flats and a longer sweater or flowy top. BUT, I was afraid I would be trying too hard or trying to look too youthful if I tried them. I decided this year would be the year I try it out and I purchased 2 pairs from loft this past weekend. I Am saving this post for some style inspiration.

  9. What a great post! I love the examples but most of all I loved looking at you wearing them in real life. Perfect outfits and as a 55 year old I am always wondering. Covering the crotch is essential and some ladies really rock the look. I am going to try to find some of your options and see how they work with me. Thanks!

  10. Even though I’m a “young” 73, I’d love to give them a try for wear around the house. Loved this article!

  11. Hi Jo Lynne,

    I found your website via a google search ‘leggings over 50″. i see it was an older post, but love the leopard scarf (i love all the outfits you put together–perfect!) and was wondering wear i might find something similar.



  12. Is there a “test”, when a top feels iffy.some of the photos, i.e. the chambray top meet the minimal coverage requirement when standing still and erect, but don’t seem to offer the same coverage when reaching, bending, sitting?

    1. I think it depends on your personal comfort level. I don’t know of a “test” but definitely is something to consider – maybe sit in front of your mirror and make sure you still feel okay with the coverage. 🙂

  13. I am 53 and have some summer dresses that are appropriate for someone my age and I hit just above the knee. My problem is I have had five knee surgeries in my right leg is kind of crooked and I’m very self-conscious of it. I was wondering if it would look strange for me to wear black cropped leggings underneath it.

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