How To Wear Leggings After 50

How To Wear Leggings After 50

Leggings are hugely popular and one of the easiest garments to get wrong. Women have been reaching for leggings since they became streetwear in the 70 and ’80s. Are they still in style? How can I wear them over 50? There’s an art to wearing leggings. Women 40, 50, 60, and beyond can easily wear them with great style when you keep a few tips in mind.

Let’s start with the most important feature of leggings. It’s 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:

  • heavyweight ponte knit
  • faux suede
  • denim also called Jeggings
  • velvet
  • faux leather

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.




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.


pullon jeggings

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. Here are other ways to wear booties.

With A Dress or Skirt

Wear leggings with a dress or skirt in similar weight fabric. Floaty, lightweight dresses can look overpowered by a substantial pair of leggings. Leggings are great a great option for those dresses you feel may be on the too-short side for you.


What’s your favorite way to wear leggings?

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




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  1. sheryl
    November 13, 2019 / 3:35 am

    well said! my chosen method is flowy long blouses or tunics….with ballet flats, with the usual assistance from Soma and Spanx…

    • November 13, 2019 / 7:36 am

      I love how you put that Sheryl

    • November 13, 2019 / 4:20 pm

      I’m hopefully not hurting anyone’s feelings here but have you seen the you tube video Leggings Aren’t Pants. It’s hilarious. That being said, after that I just can’t bring myself to wear them. I am a 62 year old mother of 8, grandmother of 15 and great grandmother of 2. I am not over weight and I love the way they look on other mature women but they just feel too breezy for me. Maybe after reading this I will gutsy up and give them a try. Love your blog and all of the posts.

  2. November 13, 2019 / 4:10 am

    With a tunic length top that does definitely cover all those parts you mention!

  3. Michele
    November 13, 2019 / 5:06 am

    I only wear leggings/jeggings in the winter with knee high boots. We currently have snow on the ground and the temperature is in the teens. No bare ankles for me. Long tunic sweaters are my choice to wear with the bottoms.

    • November 13, 2019 / 7:37 am

      I love the look of leggings tucked into knee-high boots.

  4. Susan Gowan
    November 13, 2019 / 5:22 am

    I wear leggings often and paired with a tunic or dress and a flowy longer sweater or cape. They make me feel stylish and I agree there are many that need advice about leggings’ fabrics and shape. Thanks for this, Jenn!

    • November 13, 2019 / 7:39 am

      My pleasure Susan. I have a cape on my wish list this winter 🙂

  5. Charlene
    November 13, 2019 / 6:03 am

    I’ve never been good at “dressing” myself, but am trying to learn and your blog is a first step! Unfortunately I’m still confused about leggings versus tights. Other than the thickness, I don’t understand when/how to wear one over the other.

    • November 13, 2019 / 7:35 am

      Leggings should clearly be labeled as such in the name. Tights are thinner fabric, and more closely resemble opaque tights.

  6. November 13, 2019 / 7:10 am

    I usually wear leggings with a long sweater or a long blouse, almost always with riding boots. Thanks for the great tips!

    • November 13, 2019 / 7:40 am

      I love them that way too

  7. Laurel
    November 13, 2019 / 7:20 am

    Great advice! I live in leggings in the cooler seasons, and even have some with fleece linings for the coldest weather – which unfortunately were dragged out this week in the Midwest. I loved those Chicos denim leggings on you and ordered them myself. They’re sooo comfortable and look nice, too. Tempted to try a velvet pair for the holidays!

    • November 13, 2019 / 7:41 am

      Fleece-lined would be so fabulous! Cozy and comfy.

  8. Debbie Davis
    November 13, 2019 / 9:07 am

    Love leggings and great tips- thanks! BTW – your hair is looking fabulous lately!!

  9. Kate
    November 13, 2019 / 9:08 am

    This is a trend I wish would disappear unless worn only in winter under a dress for warmth. Too many women get the look wrong, and oversized tops just make us look larger than we actually are.

  10. Diane
    November 13, 2019 / 9:21 am

    I have never worn any kind of leggings because I have heavy legs and ankles. I tend to wear straight leg pants, but I look around at everyone else and I’m wondering if these wider legged pants make me look hopelessly out of fashion. I think the best fabric for me would be the ponte, but I think I already know how it will look. What’s a girl to do?

  11. November 13, 2019 / 9:53 am

    LOVE leggings, always worn with the length top you describe. I’d consider “covering the lady parts” a valid style suggestion for ANY age! Just got a new pair of black velvet leggings in the mail today to wear with an emerald green finely pleated tunic top (sold as a dress at Zara, but it’s a tunic for my 6 ft frame!) for our upcoming New Year’s Jazz in Italy trip.

  12. Rita
    November 13, 2019 / 10:01 am

    Love leggings and wear them year round here in Austin. Prefer a tunic or T with an unbuttoned long sleeve shirt over it. Boots and ballet shoes look classy and I often wear with my Birkenstock’s, in appropriate weather,due to feet issues! Great post Jennifer!

  13. brenda
    November 13, 2019 / 10:08 am

    Good info. I chuckled at you description to cover “crotch and backside”. It is sooooooo true. Airports can be a horror show. LOL Thank you.

  14. November 13, 2019 / 10:08 am

    Love this post! I wear Hue leggings all the time. They are the most comfortable and they stay up.
    I am in my 80’s but still young looking. I make sure that I wear tops that cover my bottom.
    Here in Canada you really need to wear leggings in the winter.
    Look forward to your posts each day Jennifer.

  15. November 13, 2019 / 11:01 am

    Agree with most of the comments. Airports and public events can be a hoot! As I mature, I try not to wear items that are too tight,it just emphasizes what should not be in your face.So I think the size,etc is very important.to me, skimpy clothes on an older body are just tacky!. I am easing into this very slowly. Comfy,not revealing.Opaque tights are just slightly thicker than stockings and should not be worn as legging. Even my hairdresser complains about this item of women’s clothing.(and he has a lot of attractive women working for him!)

  16. Karen H.
    November 13, 2019 / 11:07 am

    One of your best posts Jennifer! I totally agree with all your tips. Leggings are wonderfully cosy in the winter months.. I love them with sweaters, but finding the right sweater can be challenging as many this season are very bulky. Thanks for the tips.

  17. Anon
    November 13, 2019 / 11:48 am

    Just the other day, I had pair of tights that rolled down, and kept rolling themselves down. Horrid things. Today I headed out in search of new tights, so thanks for the smile. Trusted brand names are no longer an assurance of quality.

  18. Dawn
    November 13, 2019 / 12:38 pm

    Great post, Jennifer. I agree with everything….I see many young people with too tight leggings and short tops. It’s not a pretty sight! I generally wear mine with long tops and knee high riding boots. It’s a classy look, warm too here in Colorado.

  19. Sharon
    November 13, 2019 / 12:48 pm

    Apparently I haven’t yet accepted the idea of leggings over 50. I’ve toyed with the idea but need to wear what I feel comfortable wearing. I prefer the straight leg pants look especially by Eileen Fisher.

    • Kathy
      November 13, 2019 / 1:40 pm

      I agree. I like leggings for the gym or yoga.

  20. Kathy
    November 13, 2019 / 1:38 pm

    I wear tights or leggings for exercise or yoga. I wear a dress I had made in Vietnam with leggings. However, I have never embraced leggings for everyday wear. I wear skinny jeans, slim pants, skirts, or dresses. I see a lot of women who look nice in leggings but on the other side of the spectrum I see women who should wear more structured garments.

    • Sharon
      November 13, 2019 / 2:20 pm

      I feel comfortable wearing leggings to the gym as well. I’ve thought of the dress over leggings idea however it looks like “trying too hard“ – when there are so many other options.

  21. Janet D.
    November 13, 2019 / 2:02 pm

    Thank you SO much for this, Jennifer! I am SO bored with people telling us older women we “shouldn’t” wear leggings past a certain age because [stupid ageist reasons]. I hated being told what to wear or do when I was a kid; now I’m in my 60s I still hate it (of course I rarely listened then & still don’t. LOL!). I keep myself in good shape (inside & out) & wear leggings probably half the time (jeans the other half), but am adamant about keeping my lady bits under cover of flowy tunics, long loose-fitting knit tops, sleeveless tops under open shirts, long tops under longer vests. Decades of yoga have kept my butt taut & up where it ought to be & while I’ll show it off in jeans & a short moto jacket on occasion, when it’s upholstered in any knit, I (& I’m sure anyone walking behind me) prefer it hinted at but not seen 🙂 Heeled sandals in summer, boots/booties in cooler weather. Lots of big jewelry because that’s my “look”. So, seriously — thanks for encouraging us all to step out of the shadows of centuries of restrictive “shoulds” & into the freedom to strut (albeit tastefully).

  22. jmp
    November 13, 2019 / 3:45 pm

    So helpful! Thanks

  23. Mary
    November 13, 2019 / 5:51 pm

    This is a great post. I wear leggings with a dress that hits above the knee and boots. I feel fashionable and my outfit looks age appropriate …75. It is very cold here in the winter and so I prefer to wear slacks for warmth. But I look forward to spring to wear a tunic.

  24. November 13, 2019 / 7:11 pm

    Very well said, Jennifer, especially regarding the length of tops worn over leggings! Yours is good advice for women of all ages, not just those of us who are over 50. After all, leggings are not pants!

  25. Mary
    November 13, 2019 / 7:25 pm

    I love leggings and skinny jeans on everyone else, but struggle to find any to fit me that don’t feel like sausage casings. Apparently, my hips should be bigger to match my legs and upper body. So leggings that fit my legs won’t stay up in the waist. And too many jeans labeled as skinny have ankles to wide for booties. But I’m still trying because I feel frumpy in anything else.

  26. Susan R
    November 14, 2019 / 4:44 am

    I have never worn leggings. At under 5 feet, with thick lower legs and big knees , they emphasize my worst parts. And wearing any top that’s long makes me look even shorter. Sigh. I wear slim jeans hemmed as long as possible with heeled booties in the winter and heeled sandals in the summer. I’m sorry, but seeing women wear skinny jeans or leggings when their legs are big is just sad. There are so many better options.

  27. Ana
    November 15, 2019 / 8:58 am

    Hi Jennifer
    Thanks for this post. Has anyone else tried compression leggings? They are fantastic for reducing any inflammation from sports injuries and to control pesky spider veins. Young men at the gym wear compression tights or socks to improve circulation. I wear black compression leggings, everywhere, with slip on sneakers, combat boots or sandals. And I’m always struggling to find “appropriate “ tops, as you described so well. Why don’t bloggers discuss the benefits of compression leggings?

    • November 15, 2019 / 12:51 pm

      I haven’t tried compression leggings so I guess that’s why bloggers don’t talk about it. What’s your favorite brand?

      • Ana
        November 15, 2019 / 4:51 pm

        I have Sigvaris leggings and knee highs. 15-20mmHg, refers to the amount of compression. There’s a lot being written about the health benefits of compression, including for air travel. And the leggings fit right into a wardrobe! Now if I could find some good sources for tunics that check all the boxes as you described!

        • November 16, 2019 / 5:26 am

          Thank you Ana

  28. Maleah
    November 23, 2019 / 4:07 pm

    I have a chronic illness and some days leggings and a T-shirt are all I can manage.

    • November 23, 2019 / 5:33 pm

      I’m so sorry! Wear what feels best to you.

  29. Alice
    January 11, 2020 / 10:54 am

    Wear what you want, regardless of age, as long as you wear it with style and confidence. Please take a look in a full-length mirror before leaving home, though. The admonition to wear a top that covers your crotch and buttocks is an excellent rule of thumb.
    I’m 73, not overweight, in good physical condition (I work hard to maintain that), and I wear leggings frequently. However, I buy my leggings a couple sizes larger than my regular pants to allow ease in fit – slightly fitted but not tight.

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