How to Rock Leather Leggings at 40, 50, and Beyond

Leather leggings are edgy and sexy, so they can be challenging to wear after 40, 50, or more.  Nailing the look, so you appear chic and not cheap depends on what you wear them with. For example:

Don’t wear leather or faux leather leggings with

  • short tops
  • tight tops
  • flimsy and see-through tops
  • very sexy tops with deep V-necks and cutouts
  • tall, leather high-heeled boots
  • anything with biker gang details like buckles, studs, and chains
  • weighty, masculine pieces
  • too much glitz, shine
  • cheap fabrics
  • too much jewelry
  • too many accessories
  • piles of make-up
  • big hair
  • stilettos
  • head to toe black

DO wear Black Leather Leggings with:

  • tops that flow and are not too tight, so the silhouette is broader, looser on top and narrow, skinny on the bottom
  • tops that end below your hip bones (minimum) or cover your bum, or go even longer
  • cozy, loose, slightly oversized sweaters
  • narrow cut ( but not tight) blouses and shirts
  • tunic style dresses or tops
  •  blazers layered with a long top or sweater underneath
  • sporty and classic pieces
  • feminine touches like lace or peplum
  • long boyfriend cardigans and cascading sweaters
  • rich fabrics like cashmere, silk
  • trench coats, peacoats
  • color- brights or neutrals
  • tops with details at the neckline if you are wide below to draw the eye upwards
  • few accessories- leather pants are a statement on their own
  • Shoes or boots in black like your leggings to create a long, lean line. Flats like smoking slippers, ballet flats, and booties work well.
  • Check out the way I wear my faux leather leggings
Spanx faux leather leggings tunic
tops to wear with leather leggings
Need any ideas for tops to wear with leather leggings? Try a bright jacket or a boyfriend cardigan. Yes, that is Martha Stewart wearing leather!

What Tops should you wear with Leather Leggings?

There are many tops you can wear with leggings, which I will show you below. What’s common about all of them is they cover your bottom. The best tops to wear with leather leggings are:


Leather Leggings Outfit - Black with olive tunic

1.   Long Shirts

A long shirt covering matte or silky adds a feminine touch to leather leggings, which have a masculine vibe.




Leather Leggings Outfits - Brown Leggings

2. Cozy Sweaters

A long sweater looks relaxed and cozy, while leather pants give your look an urban edge. This black turtleneck looks great with these brown leggings. Notice the cool faux croc print, which adds some nice texture and personality to this outfit.



Leather Leggings Outfits - White Stripe

3. Long Cardigans

A long open cardigan looks super sleek over black leggings and a tank top. This outfit looks super sporty with these athleticwear-style leather leggings that are new from Spanx.

4. Dresses with Faux Leather Leggings

You can wear a dress with leather leggings, but it has to be the right dress. A short sweater dress with faux leather leggings is a chic look. Pair it with booties or your favorite slip-on statement sneakers.



Leather Leggings Outfits

5. Tunics and Knit Tunic Sweaters

Any tunic or tunic sweater looks great with leggings, particularly if it flares out a bit at the bottom. When it has an asymmetrical hem, it gives an artsy look. A solid color is always striking with black leather leggings, or wear a print with a bit of black in it to tie in with the black leather leggings.

6. Blazers

Wear a slim-fitting but not baggy t-shirt ( untucked) + a blazer + leather leggings to look chic. This is a dressier version of blue jeans and a top. Layering pieces help you create a wide to narrow shape that is very slimming.

7. Ponchos

A poncho is another knit that looks great with leather/faux leather leggings. A poncho + leggings + riding boots is a very chic look.


Best tops to wear with leather leggings - Green Suede

Not Sure about Leather Leggings? Try Suede Leggings, Instead

If you can’t quite wrap your head around leather leggings but want more of an edgy look than a Ponte legging, try suede leggings. They are hip but also elegant.

One final note: I recently bought faux leggings, and after wearing them one, they stretched out, so you may want to think about going one size smaller. Check with the salesperson how much they are going to stretch.

Do you have ideas for what to wear with black leather leggings? If so, please comment or send me a photo. I would love to post it. 

Join the Conversation

29 thoughts on “How to Rock Leather Leggings at 40, 50, and Beyond

  1. I love seeing my almost-50-year old wife in tight fitting faux leather leggings. I wish she would wear them more often!

  2. I’m a bit confused by these comments honestly. I wasn’t sure I wanted to spend the money on these. But given these comments, I think I will.
    I’m turning 50 this year. I plan to wear them with combat boots. I’m not ‘trying’ to be hip. I’m finally finding my style. Plus – I’m tired of older women being invisible. Faux leather pants, combat boots, blue hair. No one is going to miss me. :) Haha!

    I’m also confused why we need to wear these with super long shirts. I’m 5′ 1″. Super long shirts make me look dumpy.

    Plus – I still have a nice behind. Isn’t the point of these to show that off? I mean don’t get me wrong – I don’t look 20 -but whose to say I stopped being sexy after 35?

    1. Hi Ali, these are general guidelines. You are right, that if you are short you don’t want to wear a long top but you may want to have one that at least comes just past your hipbones or if you can find faux leather leggings that are more of a jeans style legging rather than just an elastic waist, wear them with a short top or a top half tucked in. You sound like you are having a lot of fun with your style!

  3. I just got my black leather leggings, and I wear them with a loose fringe sweater over a lace fringed white tunic that hits my upper thigh and Chelsea booties. Although I don’t see why I couldn’t wear my black leather leggings with tall, flat leather boots? I’m short and mildly heavy so I would think this would be elongating. Maybe I’m fooling myself. Lol.

    1. Hi Elle,
      If your flat tall boots are the same color as your leggings you legs will look fine. It’s when they are a contrasting color to the leggings that your legs with look shorter, so do it! Cheers, Deb

  4. I am totally on board with the leggings, but please let’s be real for a minute; there’s a lot of people out there that shouldn’t be wearing leggings. I see a lot of very heavy girls wearing them, and you can see everything because they wear them like two sizes too small they don’t cover up anything. They wear a crop shirt with it and have rolls hanging over the top. I’m all about being comfortable with yourself, but you’ve got to present yourself properly. I’m 5 foot nine, I’m a former Marine and model, and I’m still in really good shape. I just turned 50, and I look like I’m 32. Thank you, mom and dad, for the good Danish genes, but it’s a lot of work to look like this. If you want to wear nice things, please present yourself in a ladylike manner.

    1. Hi Lisa, I think the problem is when women wear very thin leggings, and also when they don’t wear a top that is long enough. Your top should at minimum cover your bottom, and can even go as far down as to a inch or so above the knee. It’s different for every woman. This is the most flattering way to wear leggings.

    2. In reply to Lisa, So you are saying if you want to wear nice things, everyone needs to look like you? Also what does being a marine have to do with anything related to fashion? I saw a woman the other day on the beach in a bikini…she was actually FAT, but she was sexy because she rocked it and strong enough to be herself regardless of what people like you or anyone else think of her size. I was actually jealous of her because here i am, working so hard to look a certain way, and here she is, not TRYING at all, wearing what is comfy to her and loving herself in spite of extra weight.

      Really, why should heavy girls “cover up’ anything? Because it would make YOU feel better? Like you say, you have a great body, so why can’t you just rock it without putting down heavy women who choose to show a bit of flesh. Just because you work out hard and are brainwashed into being the way someone else tells you you should be, don’t be mad at women who feel comfy enough with their less than perfect bodies to show them off once in a while. I think it is attitudes like yours to cause many of our young girls to get eating disorders

  5. I was on holiday for my anniversary in New York and picked up some faux leather leggings at the LOFT. I have worn them twice to work and on the weekend. To work I have worn them with a blousy tunic and longer cable knit sweater. On the weekend, an oversized sweater and vest. I am on the heavier side, but with the right top (covering my bum), I feel totally confident in these. Thanks for the post Deborah! .

  6. Women of any age can wear leather leggings with the right top and shoes. Older women will look great in a tunic and heels and younger women can rock leggings with sneakers or high heels.

  7. They look okay on celebrities or people who have the body, but I don’t for a 50-year-old and it then just looks like you are trying too hard. Like you are trying to look young and trendy and hip, rather than just look nice and classic and more age-appropriate. I guess I don’t like the look of older females trying to wear what their 20-year-old daughters would wear -like leather leggings or ripped jeans. That’s just me, though.

    1. It’s about looking good and feeling good about how you look, no matter what your age. None of the suggestions here were about defying your age, just looking great despite it. I don’t think any of the outfits mentioned would make a 50 year old woman look like she was trying too hard. It IS possible to be trendy, and even hip, at any age without appearing tacky and the suggestions given in this article are right on point for just that.

    2. Elaine, When you’re 50 I hope you only wear baggy elastic Alfred Dunner pants then, because that’s the logic you’re giving out.

  8. Deborah,
    My husband bought me leather stretch leggings for Christmas. When I opened them I thought to myself “oh no”. The next weekend I wore them out to dinner then to the mall. Two sales ladies complemented me and told me I “rocked” them. I am tall and curvy and must say they are very comfortable. I wore them with a long J Jill tunic and pretty long scarf. I am 59 but feel 40. Thanks for your website. I love reading it!!!

    1. Hi Debra, That’s exciting. Isn’t it great when you try something new that you are a little nervous about, but then the compliments coming rolling in? Sometimes we get so set in our ways thinking we know what, or what does not suit us, that we get stale. Good for you for going for it! I always say when when you look good you feel good and life is so much more fun. And isn’t that what’s it all about – just having some fun. Cheers, Deborah
      p.s. here is a post on leather leggings in case anyone else is interested in trying them: https://www.fabulousafter40.com/how-to-wear-leather-leggings-at-40-50-and-beyond/

  9. I was totally on board with the whole leather legging look, but my husband informed me that I’m too old!!
    I should have left him at home when I went shopping. ;-)

    1. Hi Darlene, sorry to hear your husband doesn’t like you wearing leather leggings, I personally think women of any age can wear them, so I shouldn’t let him stop you from wearing them.

  10. I think are ok if paired with a chunky sweater to play them down a bit. Just like animal print IMO….just a touch is enough . I may try leather leggings, but I need a tall size which can be a challenge.

  11. I love them, and I think you look amazing in yours! I haven’t yet purchased a pair, but soon. I love skinny jeans and leggings. I am curvy, smaller person at 5’6″ and 124 lbs. With that being said, I tend to like more fitted clothes. Big and baggy things look terrible on me. I get lost in them. Maybe the (faux) leather leggings will be a purchase I’ll make this weekend. :) Thanks for sharing.

  12. I did not feel nervous at all when buying them: I was really enthousiastic then. But now they have been waiting in my closet for over two months. Because I do feel nervous wearing them for real! Every time I put them on in the morning I change into something else after looking in the mirror, thinking I look too old and too fat.

  13. Hello I read this particular article with great interest as I was on Rogers TV just yesterday talking about how to edit your look, saying exactly what Debora is saying about toning down the accessories. I was considering making a pair of faux leather leggings and was planning how to wear them, the advice given is excellent there is no reason why someone over 50 can’t look hot and edgy! I would encourage women to be bold and follow their hearts when it comes to personal style *note I did not say fashion*. Fashion trends come and go but true style it lasts forever.

  14. Oh no, don’t like them
    not one bit
    think they are most definitely something to be worn
    only by those under 35.

  15. I love wearing leggings and I am 60+ now and I think I rock leggings. I bought a pair of leather leggings but have not had the nerve to wear them in public yet. What do think? I would like your opinion if I should step out in these.? How do I send a pic of me wearing leather leggings.

    1. Today I wore my leather leggings out in public for the first time. It was no big deal like I thought it might have been. Actually it was no different from wearing any of my other leggings out and about. No body took any notice of me as I proudly strutted around the mall feeling like I was 20 again. I hope my leather leggings don’t go out of fashion before I get a chance to wear them out.

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