7 Ways to Tastefully Wear Leggings or Skinny Jeans Over 40

Leggings are casual, comfy and perfect for the 40+ lifestyle. But how do you wear them in a way that doesn’t make you look 1) fat or   2) like a desperate older woman? Check out these stylish examples.

1. Wear Leggings with  a Jacket  

With leggings or skinny pants you want to create that slimming silhouette that is wide at the top and narrows all the way down to your ankles. A jacket with a good shoulder and some nip-in at the waist gives you great shape, the same way a clothes hanger gives a flimsy t-shirt structure.

A sparkly boyfriend jacket and skinny black jeans- Twiggy’s rockin!

You can wear any color or style of jacket you like. This one just happens to be sparkly. A jacket is a no brainer way to achieve this look. You see, as we age our shoulders start to slump and round and our whole body gets softer and curvier.

A longer jacket like this one, as opposed to one that ends at your waist, is the most flattering if you are a gal who has any weight around your midsection that you want to conceal. No matter what jacket you choose a jacket worn with leggings or skinny pants adds an air of maturity and sophistication.

2.  Wear Leggings with a Top that Drapes

Wondering what to wear with leather leggings? When you wear something tight and skinny on the bottom like leather pants,  it’s complementary to have something loose and wider up top to balance things out. Save the tight on the top + tight on the bottom look for the “youngins” and go for this more sophisticated, classy way of wearing leggings or skinny pants. If you’ve wondered what to wear with leather leggings, here is a great example. This elegant draped tops works beautifully with the buttery soft leather pants to create a classy, but relaxed feel. Jeri is very slim so she can get away with this top being shorter, but if you have a tummy or bigger hips or thighs then by all means wear a longer top that covers your bum!

Jeri Ryan

Soft leather leggings and a soft draped top create a classic look for Jeri Ryan.

Also, If you are going to wear a shorter top like this with leggings, make sure the leggings are really thick, almost like pants. Nothing worse than a woman who looks like she is wearing a short top with leggings that look more like leotards with the feet cut out, everything shows! Too much information and that’s embarrassing. You know what I mean!

    3.  Wear Leggings with Sexy Heels

Wondering what kind of shoes to wear with leggings? By day, for running around in, ballet flats are fab with skinny jeans and leggings, but if you want to sexy things up later on a killer pair of heels will really make you look hot. Choose pointy toed pumps or strappy high heel sandals like these in the same color as your skinny pants to lengthen you leg, or you could also pick a nude shoe.

I think these cutout black heels are a perfect choice for this outfit. So chic. Not skinny Minnie like Angie Harmon? Just wear a longer, slighty looser top and you can still look like a star.

Angie Harmon

Angie Harmon – Black leggins and sexy black heels lengthen her legs.


4. Wear Leggings With Long Top or Tunic

Here we go….. This is what I’ve been talking about. Here is a longer, looser top worn with thick leggings. Now you could go with an even longer top if you wanted. If you are self conscious about your thighs then  a couple of inches above the knee would look fine too. As far as color goes, one of my readers was asking what to wear with grey leggings…This is a great look to copy. Rosanna Arquette has paired her grey leggings, not with black (which would have been very predictable) but with graduated shades of nude. It’s a very understated, modern look you might want to try.

Rosanna Arquette

Rosanna Arquette- The sparkly nude top softly accents these chic grey leggings.

5. Wear Leggings with Tall Boots

When flats make you feel short and high heels feel like hell, a tried and true recipe for what to wear with leggings is a great boot. Tall boots with flat heels, wedge heels  chunky or slim heels look fab with leggings and skinny jeans. They just go, and they make you feel really sexy and hip when you are wearing them.

Reba McEntire has the right idea about what to wear with leggings and boots. She’s chose a cute fitted jacket that nips in a the waist, to make her look slim and complete her look.

Reba McIntyre

Reba McEntire in her signature leggings and tall boots.

6. Cardigans are Classy

Sometimes you don’t want to wear something as formal or structured as a jacket so a cardigan is a good option. This cropped cardigan is a cute item to pair with leggings or skinny jeans and a top to look lady-like.
Notice that all the detail at the shoulders and collar give this cardigan visual width the way a jacket would. You get the same slimming effect as a jacket.

Maria Menounos

Maria Menounos looks lovely in a black cardigan paired with skinny jeans.

7. Monochromatic Makes the Grade

If you really want to look slim wearing skinny jeans then dress in all one color from head to toe. One streak of color or monochromatic tone-on-tone dressing tricks the eye creating a long thin line that makes you look taller and slimmer.

This long scarf Reba McEntire has hanging down in front also creates a vertical line that doubles the slimming effect. Stars! They know all the tricks!

Reba McIntyre

Reba McEntire- All one color makes you look long and lean.

How do you wear your leggings or skinny pants? We want to see. Send me an email with your photo and I’ll post it.  Just email to myphoto@fabulousafter40.com

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  1. Gardeners Detective says:

    I am 62 & finnaly broke down & bought a black & Brown pair of leggings. Not only did I pulled them off with long tops, everyone keeps asking me how much weight have I lost? Just another bonus to updating my wardrobe to more form fitting fashion.

    • Wow that’s great!! Funny, I just wrote a post about taking style chances like that this fall. Take a look: http://bit.ly/1ZSmLol
      Cheers, Deborah

    • Janet Darbey says:

      Congratulations on finally buying some. I love the way they look with knee high boots and friends ask how much weight I have lost when I wear them. I am sixty and totally rock this look in the winter months here in Greece.I just bought two pairs with faux leather on the front, one in black and one in burgundy.

  2. Thank you so much for this.I wish all woman look themselves closely in the mirror before they step out of their houses and asked themselves-Is what I am wearing, appropriate? I get shocked when I see some ladies wearing tights and t-shirts above their hips when going to work.

  3. Shelli Vallandingham says:

    Hi Deborah
    Have a pair of great black leather leggings. How should I dress them up for an evening out? I’m 57years old, 6’0 and 135lbs Thanks!!

  4. Maria Antonelli says:

    What are the essential pieces for a summer wardrobe for a fifty plus, in shape woman? Are capris still fine to wear if I am not a fan of shorts?

    • Hi Maria, You can wear capris but make sure they are tapered. Nothing worse than capris that look like they used to be pants and have been cut off at the calf. I would suggest that skinny cropped pants that end above the ankle. They are more chic than capris which can cut your at your widest part- your calf.

  5. After reading this article and I went and purchased my first even pair of skinny jeans! And a first ever sparkly loose top!. I would have never thought that I could pull off look like that if not this article! Feeling great!

  6. Holly Lovegrove says:

    I would appreciate photos, not of skinny and surgically-enhanced movie stars, but of genuine normal everyday-built women wearing these same “fashion tips” above for skinny pants/leggings. I can see these in any magazine at the hairdresser’s; what I would more expect from your site are examples of how this works in real life with real-shaped woman.

    • Hi Holly,
      We feel your frustration. At Fabulous After 40 we daily invite readers to send in photos of themselves in various outfits so we can show some real life examples. We post every one we receive, but we always need more. We’re working on it. If you or any other reader would like to submit a photo of yourself in leggings or a cute outfit, we’d love to post it. Please send to myphoto@fabulousafter40.com

  7. Wanda Jollymore says:

    Most of the leggings in the photos look more like skinny pants than the skin-tight leggings we are used to seeing. I prefer the skinny pant look, actually.
    I was just in Hong Kong, where I always watch the street fashions to see what will be appearing on our streets in a year or so. I saw nary a legging this time. So my guess is that it is a trend that is on its last legs. Enjoy it while it lasts.
    The thing that I saw everywhere I turned was navy blue – navy blue anything – suits, dresses, pants, printed tops and dresses, shoes, hose. All I can say is that I was one happy girl when I saw that on the streets. Navy is, hands down, my favourite ‘basic’ color.;