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) heavy or 2) like you are desperate to be young. Check out these stylish examples.

1. Wear Leggings or Skinny Jeans with  a Jacket

Your dressing goal for wearing leggings or skinny pants is to create a slimming silhouette that is wide at the top and narrows all the way down to your ankles. A jacket with strong shoulders and that nips in at the waist will instantly give you a fabulous shape.

How to Wear Leggings over 40 | Twiggy in black leggings and sparkly jacket

You can wear any color or style of jacket you like. This one 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 jacket gives your body structure, the same way a clothes hanger gives a flimsy t-shirt structure.

Leggings Over 40 | Kim Cattrall Black leggings, floral long top

A long jacket that ends at your waist is the most flattering if you have some weight around your midsection that you want to conceal, or you can wear a shorter moto jacket like the one above layered with a long top underneath. No matter which jacket you choose, a jacket worn with leggings or skinny pants is very sophisticated.


Leggings over 40 | Jeri Ryan Leather leggings and draped top

2.  Wear Leggings with a Top that Drapes

When you wear something tight and skinny on the bottom,  you need to wear something that is a little looser and wider up top to balance things out. For example, If you’ve ever wondered what to wear with leather leggings, here is a great example. This elegantly draped top 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!


Leggings over 40 | Meryl Streep Leggings and red top


Also, If you are going to wear a shorter top like this with leggings, make sure your leggings are thick (Ponte fabric), almost like pants. The leggings Meryl Streep re wearing are a good example. You don’t want to look like you are wearing stockings and forgot your pants! Too much information and that’s embarrassing. You know what I mean!

Leggings over 40 | Angie Harmon, black leggings and heels

3.  Wear Leggings with Sexy Heels

Not sure what shoes to wear with leggings? By day, for running around in, ballet flats are fab with skinny jeans and leggings. However, for evening, when you want a sexy look, a killer pair of heels will 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 your leg, or you could also pick a nude shoe.

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

Leggings over 40| Rosanna Arquette Gray leggings, long tunic top

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. 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.

Leggings over 40 | Reba McEntire in black leggings and black tall boots.

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 high boot. Tall boots with low or flat heels look fab with leggings and skinny jeans and will make you feel sexy and hip.

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

Leggings over 40 | Maria Menounos in black cardigan paired with skinny jeans.

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.
Leggings over 40 | Lynda Carter- black leggings, black jacket

7. Monochromatic Makes the Grade

If you 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 monochromatic outfit on Lynda Carter creates a vertical line that has a slimming effect. Stars! They know all the tricks!
Join the Conversation

13 thoughts on “7 Ways to Tastefully Wear Leggings or Skinny Jeans Over 40

  1. 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.

    1. 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. 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. 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?

    1. 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. 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.

    1. Hi Holly,
      I feel your frustration. At Fabulous After 40 I invite readers to send in photos of themselves in various outfits so we can show some real life examples. I 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

  7. 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.;

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