5 Style Tips for Wearing Autumn Leggings Over 50

Over 50 Feeling 40 Style Tips for Autumn Legging Looks

Happy Monday, all!  I have noticed so many of you comment on your love of leggings lately I thought I would also share my love of leggings and how much I wear them during autumn!  So, to follow are five style tips for women over 50 for wearing your leggings this autumn. 

Over 50 Feeling 40 Styling Black Leggings by Joan Vaas
I think whenever I am retired…if that ever comes…I will wear leggings the majority of the time.  I do love the comfort and style of a great pair of leggings.  But, because I have worn them so often for so long, I think I have learned a few things.
1. Make sure the leggings you wear are of the thicker, higher quality fabrics.  If not they will show every dimple., ripple and bump.  I don’t think most of us want that to happen.  The leggings I am wearing here and which are my favorite are by Joan Vass.  This is a brand you can purchase at high end retailers like Neiman Marcus, but I found these at Marshalls (perhaps 6-8 years ago) for $19 and I have worn and washed them over and over and over again.  They still look new to me.
2. Your best friend when wearing or trying on leggings is a three way mirror.  Leggings are one garment you should look at from the back before going out. Enough said.
3. Naturally, then, leggings look the best with long tunic tops and that is my favorite way to style them. The tunic style with the thinner bottom is flattering on most women. Here are a couple of my favorite legging looks from the past on the blog (you can see my hair has had many personalities!):

Over 50 Feeling 40 Styles Denim Leggings


Over 50 Feeling 40 Wear Red Leggings

4. I personally love the look of leggings with flats…and occasionally boots.  I believe flats with leggings are a very classic style and just work so well together.
5. Beware of printed leggings.  Sometimes they do make us look larger, and if you don’t want that then be aware of it.  The eye will go right to the printed bottom, so you want it to work in your favor.  Leggings come in all shapes and sizes so have your fun with the top pieces and accessories.
Over 50 Feeling 40 accessories for leggings
My outfit today features with these Joan Vass Leggings a Joseph Ribkoff tunic and, (one of my favorites), this beautiful Soft Surroundings topper that I have owned and worn also for several years.  The Joseph Ribkoff tunic is so flattering because of the V neckline and the long line of buttons which places the vertical eyeline where we want it.  The bracelet is a past purchase from a a Premiere Jewelry party represented at the time by a co-worker.  It is a beautiful piece and just seems to go so well with the style of the topper.
I am so excited to tell you that I found these exact same leggings on sale at Neiman’s last call.  They are more than I paid at Marshalls, but they are worth it and I love the step design at the bottom of the legging…it is on mine though not easy to see.  I placed these in the slideshow below and highly recommend.  My second favorite pair of leggings that I wear often are from JJill.  I like their leggings very much.
As I said have fun with the styling.  Legging looks are so much fun with all of the great tunics and accessories…you can really get into the creative part of fashion with these styles.  On Wednesday, I am going to introduce a new feature on this blog and I will also be showing another legging style you will not want to miss.
Does anyone have something to add or a comment when it comes to wearing leggings?  Please share…and I have some great pieces in the slideshow for those of you who love these styles.  Thanks for being here and


  1. Leggings are the one garment that is taking me a very long time to feel comfy wearing. My legs are “very shapely” to my eye…I feel like my thighs are on display. If I wear the leggings larger, then I am constantly pulling up the waistband! I am wearing my leggings around the house (so comfy!). Maybe one day I will feel comfortable to wear the leggings out & about (I love ruanas & long tops!), but the close fit of leggings on me is a still a no-go. (no skinny legs on me! lol)…BTW, yours look great Pam! I just get this self-conscious feeling.

  2. I, too, love wearing leggings and agree they need to be worn with longer tops (at any age). I normally wear them in the winter with tunic length sweaters and tall boots.

  3. Although they aren’t technically leggings, my favorite slim bottoms are from Duluth Trading, their Slim Leg NoGA Pants. They function as leggings for me but are not quite as form fitting. I wear the 33” inseam, although they also come in 29 and 31 inch. This line also includes several styles including actual leggings which are reinforced with Spandex.

  4. I also wear leggings often. I found black ones when I used to shop at Coldwater Creek (when they had the retail stores) and they were so perfect that I immediately bought a second pair, also black. Still on the first pair, but I don’t want to be without them, thus two pair! I do have other colors and subtle prints. I love the ones from Soft Surroundings! I agree, they should be worn with rear-covering, and for that matter front-covering tops like you are showing here. As you said, they look especially nice with flats! Fun seeing how your hair styles have changed, and this time lapse also shows just how enduring this particular garment has proved to be.

  5. Yes I do wear leggings, only black or deep navy and yes, higher quality , better fabrics, and with a long tunic top that covers…..well, you know! Lol.
    I feel great in them!

  6. I could just say that I, too, like leggings and wear them all the time. Or………I could tell you that in preparing the wardrobe for winter I did an inventory and I have 10 (!) pair that are “good” ones……..and about half dozen that have seen better days but are good enough to wear when a messy project comes up. Yup, I like leggings. Nope, I won’t be buying any this season. Mine are mainly black, one small polka dot print and a couple of shades of grey.

  7. I also have a few for messy situations, but my husband told me recently my messy clothing needs to go because I am not messy enough!! Thanks for sharing, Carol!

  8. I am a young (! ) 70 year old grandmother, and I am enjoying leggings. I also prefer thick high quality leggings that aren’t too tight. I wear them with long tops and sweaters. I think they look great with flats, slip on sneakers and knee high boots. Comfort is key! You look fabulous in yours….it’s a great look for you! Very classy!

  9. I’ve liked leggings for as long as they’ve been out, but I really like the newer ones with more structure, thicker ones, like pointelle blended. It took a great concept and made it more fashionable for women “over 20”. (yes, I meant 20). Also they hold the tummy in a bit.

  10. That’s how my Joan Vass leggings are structured…to hold that tummy in a bit!! Thanks for bringing this up Nina…it sure helps!

  11. I have leggings from White House, Black Market, Philosophy and probably another brand or two. Last year I bought some Utopia by Hue leggings in knit denim. They have become my go-to’s. I just bought a second pair of dark blue so I have a back-up in that color. I also have a lighter whiskered blue. I liked the first two pair so much that I bought a white 7/8 length for summer and I recently bought a black pair. They are comfortable, have rear pockets and fit my more relaxed, retired lifestyle. I always wear leggings with tunic-length tops. Lately, if I want a more dressed-up look, I wear slim-fitting Juliet-style pants from Chicos. They skim ruther than hug my rear and thighs so I can wear shorter tops with them.

  12. Love the legging look. I agree, take a look from the back to be sure the bottom is covered. Love your look Pam. ?

  13. I like wearing leggings under sweater dresses- especially during the transition to fall when I am still wearing ballet flats.

  14. LOVE leggings and do have my fare share in different weights/textures, also in colors and a few patterned ones. (Actually just ordered some in a (stretch) velvet for dress-up wear.) As a result I do not have a favourite brand; as choose according to my need. Yours look marvelous on you BTW.

  15. Thanks for your great article. This has been a tough topic for me because as a professor, I work with so many young adults that are wearing leggings in a way that leaves nothing to the imagination. In my role, I often try to model how to wear leggings in the workplace and have to have difficult conversations with students so that they will excel without judgement about their appearance.

    I do love the JJill leggings. Chico’s also offers great leggings but my my all time favorite come from Uniqlo. Uniqlo offers many different thickness and styles as well as sizes. Admittedly, their clothes do run small but you really can’t beat the price.

    Thank you again!

  16. And thank you, Kathe…..sounds like you are a special professor! Thanks for all you do!

  17. I’m a big fan of leggings! I prefer heavy weight fabrics for smoothing and coverage. It’s not always easy to get leggings right when you’re petite. I goy some velvet ones last year that are amazing.

  18. I also love leggings with long tops of course. I’m happy to read about different brands. My go to favorite are Lysse’. They are a heaver knit with a very wide band at the waistline. I buy mine from Nordstrom.

  19. I have found great “leggings pants “ from Uniqlo that are thicker and fit me well. If I buy a lighter color, I size up and then alter the elastic waist in the back so they don’t droop. I am also enjoying a pair from Talbots in a gorgeous grey that are jeans weight bought in my usual Talbots size for a perfect fit. They are called “sculpt jeggings.”

  20. I think we are going to look back at leggings and shudder. I’m not talking about slim fit pants or skinny jeans, I mean painted on leggings. A women’s wear shop owner in my town has the mantra “leggings are not pants”. Her advice, if you insist on wearing them, go out in the sun and make sure they remain opaque.

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