The Modern Way To Wear Leggings After 50

Anyone who tells you that leggings are dead or women shouldn’t wear them is sadly mistaken. With more of us living casual lifestyles, leggings can be a great fashion option, when worn with attention to a few details. 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 help you look fabulous wearing leggings.

over 50 fashion blogger jennifer Connolly wearing talbots Ribknit poncho in Blackwatch Plaid


woman wearing lysse white leggings for spring with blue tunic shirt

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 tunics and leggings still in style? You bet. Can you wear them and still look polished? Absolutely! Can older women wear leggings? Yes!

Related – Leggings For Spring


Here are the best leggings to wear over 50 and tips for wearing them. Let’s start with the most important feature of leggings…the fabric.

You might also enjoy  What To Wear Instead Of Leggings This Fall


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…no these are not just for young women and yes, they are comfy!

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

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 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 than faux leather and feel more relaxed. Here are some great options.

Related – How To Wear Leather Leggings over 50



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 For Leggings Over 50

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
  • dresses, both long and short
woman wearing velvet leggings with a dress

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 the 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.

over 50 fashion blogger showing how to wear leggings after fifty

Shoes To Wear With Leggings Over 50

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.

Related – 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.





  1. I wear leggings with slip on sneakers or vans but they are kind of dressy sneakers.

    1. I wear leggings with Vans slip ons, or Tory Burch ballet..

  2. 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.

    1. Liz Hawthorn says:

      My sister says we need Mirror Police when we see someone who has just dressed, left the house and not bothered to look in the mirror, especially at the back!

      1. I agree, it’s so embarrassing when someone wears them so transparent and tight to their body that looks like they are naked. That is so unacceptable. They probably don’t have a mirror at home, or maybe they do but purposely wanted to get attention. That’s the wrong way to wear them, and specially some are truly excessive curvy and wear them with short tops! We truly need a police patrol, or someone with the best intentions to explain what is acceptable and looks nice and what doesn’t. Be trendy, but please, have good taste, don’t make others feel uncomfortable around you!

      2. Betty J Dickison says:

        Sometimes …..you just have to wear what you have available to you.

    2. Terry Applebaum says:

      Love your comments! I do the same at 66 years old. I dress to make me feel great for myself everyday. My daughters always wants to know where am I going today or where did I go. They’ve since stop asking. Retired for most of my life and itching to go get a part time job but my husband said “No” plus I/ we travel a lot. ❤️

      1. So true!!!! Thank you for stating a true fact for many ppl! More grace and less criticism is what this world really needs!

      2. Very good tips. Thanks for putting the ‘ crotch/ butt ‘ covering reminders out there. Some women haven’t a clue…

    3. Thanks for the great idea. Never thought about buying leggings a couple of sizes larger for “fitted but not tight.”

      1. My problem is the bigger the size the more I’m pulling on them to stay up! I love leggings.

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

      1. Love this! And I love that periwinkle empire waisted long jacket in the photos. Where did you purchase that? Great idea to unbutton it to show some leg(gings)!

    1. Sometimes fashion police forget there may be a reason for
      loose-fitting clothes.

      1. Loose fitting is just fine, it’s the length that is the issue when wearing leggings or tights.

    2. Yvonne Bryant says:

      I have Lupus. I wear leggings for my infusion treatments as well as to the doctor. They are comfortable. I’m 66, and they are even what I sleep in

    3. Lorraine Logan says:

      I can understand where you’re coming from. In April this year I had my third spinal operation and leggings are jeggings Are the best thing for me.

    4. I’m right there with you.

  4. 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?

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

      1. 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!

      2. Shapermint. They have the high waist and mid waist versions. Great quality. Easy wash.

    2. I tried the pair from Soma and they were so tight that I felt I was wearing a girdle. Remember those? I had to return. They held me in but were just too uncomfortable.

    3. Stampnsnip says:

      I have started wearing compression knee highs. They are super comfy and my legs are seriously happier when sleeping, traveling, and day to day wear! I wear them with bike shorts, tshirts, and sometimes with a long sleeveless tunic. I live in the Southern California desert and it’s warm to hot all year! So like Jennifer suggested be comfortable!

    4. MaryElizabeth says:

      I wish you had given me advice when I started my nursing career 30 years ago! Compression is amazing for circulation, achy muscles and joint support! Now, if I could stand wearing in the Florida heat😜

  5. 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.

    1. Lynnette Benedict says:

      I agree with your comment about leggings for short thick legs and big knees.
      I am one of those. i also wear various jeans from slim jeans to boot cut and feel more comfortable going out into public . longer shirts coats sweater make shorter people frumpy looking

    2. I know the problem… I’m under 5’ and I love my leggings and beggings but my problem is tops. So many long tops come to my knees. It’s hard to find just the right length. I’m 79 but when I go out I like to look in style. I weigh 114. Any suggestions?

      1. Try tunics from the petite department. You can also have things hemmed.

      2. The fashion for “long” t-shirts which are high at the front with a lower back are far more flattering and all of the essential bits are covered. Alternatively, a long short t-shirt which just covers your backside is good. If you aren’t sure then wear a long cardi that’s not heavily patterned. I sometimes wear a denim shirt which goes with everything and always in fashion, great when cool but not freezing. I’m 5′ and often struggle to find reasonably priced items that look good.

      3. Me too! Knee replacement surgery and a month later in emergency finding out I have three fractures on my spin. My go to are higher quality leggings as the fabric has a better stretch in all directions. I love this article as I am close to 77 and wasn’t sure if leggings were a go to! Love the reminder that you should cover the crotch and butt! Hope more women read this article!! Thanks so much!! I’m going on 77 and when tops are too long, so I do a “half tuck”. Flattering and trendy (I still hope!!)

  6. 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.

  7. 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!

  8. 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.

    1. Mary I like the idea of leggings with a dress and boots. I just can’t figure out what dress looks right with leggings? I’m guessing one with a slim silhouette?I have summer swing style dresses I rarely wear because of spider veins. However sometimes I just say what the heck and go for it.

      1. I’m 66 and I wear leggings all the time with pinafore dresses and comfy socks and Blundstone boots or Doc Martens- so comfortable!

      2. Love your fashion ideas.
        Age should not be a barrier to fashion
        Taste and confidence trumps age any day.

      3. It sure does! We all need to wear what makes us feel confident.

  9. 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).

    1. Just got on this site and love, love it
      Great suggestions. I struggle trying to figure out the perfect length of the tops. So it’s not to long I’m 5’2”. I just turned 60 and always struggled dressing myself fashionably Although I’m getting better (thanks to my daughters). Also looking for daily easy great exercises for over 60 to try to keep fit.
      Compression leggings sounds great do you have to go up a size or two so their not so tight?

    2. Charlene Johnson-Boyd says:

      I’m 73 and wear leggings a lot of the time with longer tops, and, sweaters. When inside I choose lighter fabric weights for lounging. Additionally, I wear ballet flats or comfortable Carium sneakers.

      1. I love ballet flats with my leggings too

      2. Marion Liscombe says:

        What kind of shoes/socks in winter? I am also 73 and a larger woman but not huge. I do have a swollen knee

      3. I wear thin cotton socks in the winter.

  10. 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.

    1. 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.

  11. 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.

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

    2. Yes. I tried to like leggings. I bought 1 pair at the urging of friends. They never saw the outside world — donated. I will stick with straight and boot cut jeans. Whatever makes YOU comfortable…Happy Friday!!

  12. 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.

  13. 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.

    1. I am 66 yrs old.I never wore tights.I have always been over weight and have been prone to wear my clothes a bit baggie.I have lost 75 pounds.Yes wonderful but now I really need something to hold all of me .So I ordered leggings from Amazon.2 pairs for only $21.00!I thought they would be thin .To my surprise they are wonderful.I love,love ,love my legging,stretch pants whatever you wan’t to call them.They come in reg size,plus size,and extra plus size.
      I have only wore them in the house ,I need to find some longer tops I am still a plus size 20.I have to say they do not roll down,and they are thick.I bought high top so they generously cover my stomach without rolling down or cutting in my stomach.
      My adult children said they loved them on me and my 13 yr.old beautiful granddaughter who is my biggest critic gave me 2 thumbs up…

      1. Hello Maureen. What brand of leggings did you get from Amazon? I am also in my 60’s, losing weight and would love to check the brand out. Thank you!

      2. Yes, please! I’m 62 and gained some weight but can’t find thicker leggings that don’t roll down…I would love to know the brand, too!

    2. Yes. Had the same problem with rolling down but also realised that it happens more with certain underwear fabrics.

  14. 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.

  15. 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. 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.

    1. I can so relate to leggings in a Canadian winter! Not sure when you will see my bare legs again!

    2. Susan Armstrong says:

      You took the words right out of my mouth! Love Hue! Worth every penny and if budget doesn’t allow… you can order them on Poshmark… I have almost every colour possible!

      1. Hue makes a great legging

  17. 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.

  18. 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!

  19. 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.

  20. 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?

    1. Hi …… wear what you look good in not what fashion dictates!

  21. 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.

    1. I agree. My husband said skinny pants are for skinny bodies.
      Worn tastefully…great but many are wearing tops that barely come to their waist and there’s a lot of over throw.

  22. Debbie Davis says:

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

  23. 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!

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

  25. 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.

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

    2. @Charlene & Jennifer: I distinguish the two by referring tights similar to that of pantyhose as also include a foot but are generally opaque as thicker in fabric plus may also include a subtle pattern or texture and come in a range of colours. Whereas leggings can come in various fabrics, weight, colours, patterns and lengths plus can be worn with or without a sock. With that said; that’s my personal take on the two …. ☺.

  26. Susan Gowan says:

    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!

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

  27. 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.

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

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

    1. 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.

      1. I saw that video. It is hilarious, but I ended up ignoring it. I’m 76 and wear leggings and tunics all the time. I hope they never go out of style. Try them again.

      2. Unfortunately some women wear a short top and all the leggings exposed! Yuk yuk & yuk! Honestly they have no idea! The bum area should NOT be exposed in leggings! Ever!! Simple no brainer. I wear them all the time. So comfy. You can dress them up or casual.

      3. I agree. They look best with your backside covered:)

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