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.




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  1. 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.

  2. 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

  3. 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?

  4. 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:)

  5. 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.

  6. 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.

  7. 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.

  8. 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?

  9. Deanne
    September 12, 2020 / 5:26 am

    I have a drawer full of leggings purchased for my barre classes. I normally would not wear them at other times but during the pandemic I have started wearing them as a comfortable outfit at home, especially with some type of longer tee and then a longer cardigan as the third piece. very comfortable and warm too. I love Zella leggings from Nordstrom and added a couple pair of Everlane last winter that I like a lot.

    • Jennifer
      September 12, 2020 / 7:46 am

      I’ve been borrowing my daughters Zella leggings and love them. So soft:)

  10. Kay
    September 11, 2020 / 2:21 pm

    I have never cared for leggings on me, so I don’t wear them. They are also very uncomfortable in really hot weather. However, anyone who does like them should go for it whether they look good or not. Wear what makes you happy.

  11. Dianne
    September 11, 2020 / 1:51 pm

    I love this blog post, such a great job of describing the leggings and tops. Thank you for posting this especially for women that are in their 60’s and older. People like to tell us what to wear when we get older, such as underwear and clothes. I do not want to wear frumpy underwear or frumpy clothes or shoes.

    • Janet
      September 11, 2020 / 6:26 pm

      Yay leggings done right!

      When you sit in front of a computer for 10-12 hours a day (going on 7 months) you want comfort and these fit the bill! 💜

  12. Norma G
    September 11, 2020 / 1:06 pm

    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! Most of my leggings are heavier weight knit slim pants, fitting like leggings, but have more substance…not like typical “workout”leggings. I always wear a top that covers the crotch area and my butt and often add a longer cardigan, vest or kimono, depending on the weather, just in case my rear end is not completely covered. Tunic tops and shorter dresses also work well for me with leggings.
    I often see young and old putting everything they have on display and that just looks tacky and trashy. Age is just a number and we should all be able what makes us feel good. Looking like you don’t care or have no self respect is not good at any age.
    My next purchase just might be faux leather or faux suede leggings. I already have some faux velvet leggings that I love.

  13. Donna
    September 11, 2020 / 10:34 am

    I’ve tended to “collect” leggings and not wear them, even though I love the look! Tried wearing them just at home, but even with fleece lining, I still get too cold ( possibly the temp my hubby sets the thermostat at!)

    What are your thoughts of wearing 7/8 or capri length with either short or longish skirts? Short dresses? Long dresses? Thinking boho-ish.

    • Jennifer
      September 11, 2020 / 11:34 pm

      I think it’s a very cute look! My legs are short so I have to be careful with the proportion

  14. diane
    September 11, 2020 / 9:08 am

    I welcome your style tips – so valuable to me, as an “active 80” who simply wants to look my best without looking as though I’m imitating my granddaughter!!!!!

    So special thanks for the information of weight and colors, and how to style the rest of the ensemble.

    On this day, let us remember the lives and families of 9/11 and blanket them in God’s love.

  15. Anne
    September 11, 2020 / 8:44 am

    I wish people under the age of 50 would read your blog. I find the younger generation wear short t-shirts with their leggings! It looks horrible!

    Leggings are great and cheaper than most dress pants or jeans.

  16. Barbara K.
    September 11, 2020 / 7:34 am

    I have just started wearing leggings in the last 6 months or so. It seems that longer tunic-style tops are everywhere right now, so it’s easier to put together a nice outfit. My favorite place to buy leggings is the catalogue NorthStyle. The leggings fit me so well – not too tight around the waist (which is where I carry extra weight, darn it!) and not too tight around the bum and thighs. Comfy without looking sloppy. I bought crop length for the summer and just put in another order of ankle length for the winter. I love them!

  17. Linda Henderson
    September 11, 2020 / 7:25 am

    Still laughing about “sausage casing!” And the dark blue (sapphire?) wrap is great on you.

  18. Francesca B.
    September 11, 2020 / 7:23 am

    Thanks Jennifer for the post very timely as I wore my first pair of leggings yesterday from Old Navy with a long plaid shirt and loved the look! I did buy a pair of faux suede leggiings in the NSALE but they had a zipper right at the back and it did not have a hook and eye and it would just run…jikes… so they went back.
    Hope you and yours are ok with the fires.

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