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How to Wear Leather Leggings Over 50

Can women over 50 wear leather leggings? You bet! I found a pair last week that practically jumped into my shopping bag and screamed for me to take them home. I did and I’m thrilled with them.

Jennifer Connolly of A Well Styled Life showing how to wearing leather leggings over 50

Leather or faux leather leggings are sleek, chic and a great way to add a modern edge to your look. Their success or failure often depends on what you pair them with so here are a few tips to keep in mind.

how to wear leather leggings over 50

Leather leggings are form-fitting so they look best when paired with a looser top. Opt for oversized sweaters or tunics which cover your tummy and hips. Loose blazers and tunic length blouses all work well with leggings as do 3/4 length cardigans and coats.

Pearl embellished sweater from Ann Taylor with faux leather leggings on A Well Styled Life

These are faux leather leggings that fit close to the body without looking shrink-wrapped. Their back is a heavy stretch ponte knit which molds to your body without being tight. They have a high rise and side zipper so there’s no bulk upfront. I went up one size because I opted for petite, which is a slimmer fit.

Jennifer Connolly of A Well Styled life wearing French Kande pearl necklace

Head to toe black can look harsh with leather so choose a flattering color on top. Soft textures and feminine details are a great contrast to shiny so pair them with lace, ruffles or fuzzy textures.


Jennifer Connolly of A Well Styled Life wearing faux leather leggings from Ann TaylorHigher heels can be tough to pull off with shiny leather so I opted for suede flats. The black shoes help elongate your leg. Flat boots would work as well but I’d opt for suede over leather. Too much leather in one outfit leans toward hard, which is not a look I gravitate to. Jeannifer Connolly of A Well Styled Life wearing leather leggings

I paired mine with this winter white sweater with pearl embellished cuffs.

Have you tried leather leggings lately?

Thanks for reading ladies and have a great day!

Affiliate links within this post may generate income for AWSL.


  1. Love the look! Like others, I need to rethink wearing leather leggings at a more mature age. Question…when it’s cold, I would freeze without just bare feet/legs in flats. What would you suggest wearing with the shoes?

    1. Should say “with bare legs”!

    2. They would look great tucked into suede booties or boots, worn with socks

  2. Okay, I’m going to say it. You look hot in this outfit! The leggings and soft sweater are a perfect pairing, chic and sexy, not too dressy yet sophisticated. Now if I can just find my black faux leather leggings and cherry pink cashmere sweater I packed away, I’ll be happy!

    1. Thanks Janet:). A cherry pink cashmere sweater would look awesome with leather leggings. Dig them out and rock them!

    1. Thank you! You’re right about how they seem to make us take them home.

  3. Fabulous! You truly do look modern and attractive! Are they along with you in Japan? Hope so!

    1. They were until my last minute repack. I wish I had them here

  4. Those leggings look fab on you! I love faux leather leggings. My favs are the Spanx that you link too. They definitely suck in the areas that need to be!

    1. Thanks Cindy! One of the best features of faux leather leggings.

  5. I bought a similar pair from Chicos 2 years ago and never wore them…out of fear, I suppose. I tired them on again and now they are too big.(insert happy face here) You make faux leather look great! I might have to replace them after all. For now, I have faux suede which is an intermediate step to the faux leather. Thanks for the post, it makes me more confident about what was once a hesitant choice.

    1. I have faux suede too and love them! This is my first pair of faux leather and I’m so glad I tried them

  6. Wow! You look awesome in the faux leather leggings. I have never tried them. At this point, I thought I was too old. You have me second guessing my decision. Love this post! Thank you! ❤️

  7. Those leggings look terrific on you, nice choice!

    Did you realise that recently we’ve had to close 5 boxes to read your articles?

      1. Just checked the pop-ups on your latest post, and interestingly it’s replying that has highlighted the problem. Obviously you need to have cookie and subscription straps and a few ads are a price I gladly accept in exchange for your lovely blog. The problem is the bottom ad strap that pops up again after closing. While I’m typing this I’ve given up after closing it 8 times. It covers your photo’s, and is often an animated ad which is so distracting. Please forgive my complaining, but I don’t believe this is something you would be happy with.

      2. I will check into it! Scrolling higher may leave the bottom add below the comment box.

      3. Thank you Jennifer 🙂

  8. You look great in the leather leggings! I bought a pair last year and love them. Would love more posts on how to wear leather leggings. Your look is nice with the white sweater. I live in south florida so I need some lightweight top options when it gets cold enough to wear mine.

    1. Will do Kathy! I’ll post some options when I get home from Japan. I already have some ideas.

  9. Love those leggings. I have a pair of knit leggings with leather stripes on the sides. I was a little hesitant to go full blown leather, but now I see them on you I’m thinking I should get a pair.???? thank you for keeping us of a certain age fashion forward!

    1. I was hesitant to try them too Cyndi, but love I love them. The knit back on this pair makes them so very comfy too.

  10. You look great in those leggings! Not sure I could wear them here in hot Florida

    1. I’m not sure based on your humidity either Linda but it might be great for evenings

  11. I have been wearing faux leather leggings for about four years now and I love them. One of the reasons I look forward to cooler weather. You look great in yours.

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