The Modern Way To Wear Leggings After 50

Our world has changed dramatically in the last year and the way we dress has changed with it. More and more women are working from home which means their wardrobe needs have changed. You may need to dress professionally from the waist up for Zoom or Skype calls but you still want to be comfy and can include leggings. How to wear leggings after fifty has been an extremely popular post so I’m updating it with some new ideas and fresh resources to find great leggings.

Leggings are hugely popular and one of the easiest garments to get wrong. We’ve been reaching for leggings since they became streetwear in the 70 and ’80s. They now have style details and shapes that resemble pants, so they don’t all look like workout gear.

Are they still in style? You bet. Can I wear them and still look polished? Absolutely! Can any woman wear leggings? Yes!

Here are some ideas and tips to keep in mind to get the look you want. Let’s start with the most important feature of leggings…the fabric.


This is critical because leggings are not the same as footless tights! I’ve seen too many women traversing the airport wearing footless tights as leggings which shows the world way too much. The fabric of leggings needs to be thick, 100% opaque (not see-through), and very stretchy. They should closer to stretch pants than tights. Here are some great fabrics for leggings:

On the subject of faux leather leggings, they’re no different than other spandex leggings and they do breathe and the best fit doesn’t feel or look like a sausage casing.

Jennifer from A Well Styled Life styling how to wear leggings after fifty

All of these fabrics need a high spandex or Lycra content so they spring back in the knees and seat, Fabrics with a four-way stretch fit the best and have the best recovery. Darker colors are more slimming and dressy. Patterns are tricky so choose the smallest ones in subtle colors.

Faux Suede leggings have long been a favorite of mine. They give a softer look that faux leather and feel more relaxed. Here are some great options.


Leggings are meant to be snug but if they feel like a sausage casing, go up one size. You won’t sacrifice the style and they will be more comfortable. Choose high rise leggings with a wide, no-roll waistband. There’s nothing worse than sitting down and feeling your waistband roll down under your tummy.

tunic jacket over leggings on Jennifer Connolly

Tops To Wear Over Leggings

It doesn’t matter how shapely and fit you are, leggings require a top that covers your crotch and backside. Full stop here ladies. This is critical. Even the heaviest weight leggings look best worn with a top that’s long enough to cover your lady parts.

Leggings look great worn with:

  • tunic sweaters
  • long line blazers
  • tunic-length shirts
  • thigh-length blouses

Choose tunics with some shaping through the torso. You don’t want tight, but too boxy is just as unflattering. You’re going for length, not width and bulk. Side slits in tunics and blouses are great for elongating your legs and helping to balance the proportion. Try a knee-length cardigan worn open over a fingertip length blouse. Unbutton lower buttons of longer jackets to show some leg. Beware of extra bulky sweaters which can make your legs look like stick figures and your torso look huge by comparison. Proportion is key here.

Also see Playing With Proportion

over 50 fashion blogger showing how to wear leggings after fifty

Footwear To Wear With Leggings

So what do you wear on your feet? Knee or riding boots are a classic combination. Choose boots in a color similar to the leggings to create a long lean line. Ballet flats are another classic look, think Audrey Hepburn. Low heeled pumps or sandals look great with leggings but beware of the stiletto which is hard to get right and can easily lean toward trashy. Booties are perfect with leggings.

See also How To Wear Ankle Boots Over 50

What’s your favorite way to wear leggings?

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Thanks for reading and remember to wear what makes you feel confident.




This post may contain affiliate links which won’t change your price but will share some commission.


  1. Charlotte Miner
    June 9, 2021 / 8:43 am

    I am 64 and love J Jill leggings. I can wash and dry and they keep their shape plus don’t fade easily. I am 5’7 115 and love the looks you can achieve with leggings. Dress up or down! I don’t care for Jennings, the are to bulky for my thin legs; they just bunch up. Great article! Hopefully leggings will never go out of style

  2. Cristina S.
    April 13, 2021 / 9:57 am

    I think the important thing is to always match them with a dressy top and/or blazer (of course, appropriately LONG-ish enough to cover your “business” lol!) so it doesn’t look like a sloppy gym outfit. I’m in my 30s and might have a more casual attitude toward leggings (I basically LIVE IN THEM and don’t care about having others’, unfortunately, often sexualized judgements trying to dictate what my personal choices “should be”), but I like pairing them with velour blazers over a satin shell cami with booties or ballet flats for a professional or holiday formal situation. I have a pear shape and I feel leggings accentuate my lower-body curves in a confident way vs. something which would make me look heavier if I were worried about hiding my perfect imperfections (like constantly wearing really frumpy oversized sweaters or parkas!). Thank you.

  3. A Touch of Class
    March 10, 2021 / 2:21 am

    Love this post and all the comments! There is such a big difference in the fabric weight and stretch of leggings. I love leggings for wearing around the house, they are so comfortable!
    I always wear a top that covers the crotch area and my butt and often add a longer cardigan,
    special thanks for the information of weight and colors, and how to style the rest of the ensemble.

  4. Barb
    January 24, 2021 / 4:37 pm

    I am 71 , love clothes and looking my best , Great article , I liked it very much, I think this article would be good for younger ladies as well. Cheap thin leggings are not a good fit for most girls, and women!

  5. Sonja Cole
    January 17, 2021 / 12:53 pm

    I love your advice. I’m 80 and active. Love wearing jeggings and my jeans with pretty tops. Most of my clothes come from Talbots. Their petite pants are a perfect fit.

  6. Jane Charles
    December 4, 2020 / 7:35 am

    I am 83 yrs old & I wear leggings & jeggings. Love them.

    • Mar
      January 15, 2021 / 5:43 pm

      Good for you. I love them at 63

  7. Brenda J. Garon
    November 7, 2020 / 7:25 am

    I have avoided buying leggings – although I think I would love them(!) – because I have knobby/swollen knees from arthritis AND am, how shall we say, bow-legged.
    Do you think I should continue to avoid them?

    • Jennifer
      November 7, 2020 / 9:37 am

      If you’re not a fan of very tight ones because of your knees, you could try skinny straight stretch pants instead. Just as comfy too.

      • Beth
        December 11, 2020 / 10:44 pm

        I’m 64 and I love my leggings. I buy a higher waist style with a panel, thick knit with a regular waistband, and super tight knit fabric . I love them all, safety, snugged up and I don’t trip over my pant legs. Go for it! You might like it-I did! I just wish more had some kind of pocket.

      • Mjmeyer4
        January 15, 2021 / 5:50 pm

        What brand?

    • Christine Pezzella
      April 23, 2021 / 1:05 am

      Try leggings from Old Navy to get started. They are very reasonably priced and are often on sale. I am 73 and not skinny but they look great. I have several pair in black and dark navy. Depending on the fabric and what you wear on top, they can even be nicely dressed up. i wear them year round now – capri length in the summer – and even found some fleece ones for cold winter days and nights.

  8. Char
    November 3, 2020 / 2:57 pm

    I really like leggings and jeggins because they are so comfortable and easy to dress up or down. A third piece like a long cardigan and boots along with some jewelry and then you’re ready to go most anywhere. Definitely go up a size if they feel too tight because you should be able to move with ease:)

  9. cindy
    September 15, 2020 / 1:00 am

    This was a great post. I wear leggings all the time but only with tops that cover the bum. I totally agree about the weight. They need to be thick at my age unless I am wearing a long tunic.

  10. Robyn
    September 13, 2020 / 2:27 pm

    I wear leggings at home but rarely out. You styled them beautifully. Unless I get the portions correct I often feel I look like an apple with legs when I wear leggings and skinny jeans. At home yes, out no. I prefer straight jeans and corduroys, or trouser pants.

  11. Anna mcfarland
    September 12, 2020 / 5:44 pm

    I do not like leggings. I live in my jeggings but they are not as tight or revealing as leggings. The thicker fabric helps. Leggings do not feel polished enough or warm enough for me. I prefer my jeans.

  12. Canadian Elizabeth
    September 12, 2020 / 7:54 am

    A big THANK YOU for all of this excellent advice, Jennifer!
    Just a thought, I like to show a bit of ankle when wearing leggings because it seems to give a modern take on things and not look frumpy. What do you think?

    • Nancy Choat
      March 26, 2021 / 10:43 am


      Vancouver Island Nancy!

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