How to Wear Skinny Jeans Over 40 in 2021| Ageless Style 16

I really hate to be the bearer of bad news. For one thing, I am almost absurdly non-confrontational. I hate to ruffle feathers or offend in any way. But sometimes, in my role as your fashion friend, I have to speak truth. And some of these truths may be hard to hear. Over the years, I’ve dispensed such gems as:

Leggings ain’t pants.

Capris can be aging. Crops are not. And the distinction is everything.

Clunky shoes lead to clunky outfits.

But this one may be the hardest of them all. A bitter pill to swallow, even (especially) for me.

Let me explain. Our formerly stylish and trendy silhouette has now become classic, and bordering on out-of-style. But don’t worry. I’m here to give you the truth about skinny jeans, and help you transform yours into the foundation for modern and stylish outfits. 

Over a decade ago, when skinny jeans came into prominence, we were all wearing everything but skinny jeans, and balked at the idea of giving up our favorite denim silhouettes for this new, strange, denim-legging-looking style.

But most of us eventually did. And we learned a few things about skinny jeans that kept us wearing them.

They were comfortable.

They were versatile.

You could wear them with any heel height.

And now that many women own nothing BUT skinny jeans, fashion is all like: You can’t wear them anymore.

See what they did there? They made a favorite go-to suddenly obsolete, making it necessary for us to go out and buy all new jeans!

At first, I pushed back and stuck up for you all. I promise. I was all like “Oh no you didn’t” and stuff, but then, I started looking at the options, and I have to admit, I fell in love a little.

First of all, I fell in love with the idea of having more than one style to choose from. And of a new silhouette that combines the best (and in some cases, the worst) of the 80s and 90s.

This doesn’t mean that I am suggesting you abandon your favorite skinnies for a pair so wide you can’t fit down the aisle at Target, but it does mean that I would encourage you to look at enough images of outfits with these new silhouettes that your eyes, like mine, eventually adjust to the idea that there is life beyond skinnies.

I will say that one more time, in case you missed it. There is life beyond skinnies. And I’m here for it.

But for those of you, like me, who find yourself with a closet full of skinnies and no idea what to do with them, I’ve got answers. Here, my guide to wearing skinny jeans over 40 in 2021, and looking stylish and contemporary and flattered and all the things.

But first, a big shout out to the Ageless Style Program member who got the conversation started with this question:

Most of your models in your examples are wearing skinny pants. Is that because they’re model perfect? I have an apple shape, so your recommendation has been to wear boot cut jeans and slacks to balance the tummy. Can I ever wear skinny jeans? I just donated them to the Salvation Army.

Beverly Kolosseus

I get this question a lot, and here’s the short answer: “Tight clothes show your shape.”

If you are comfortable with your shape, and highlighting it, the skinny jeans are fine. If not, then you will want to explroe other silhouettes.

Women with apple shapes often have slim legs, and a skinny jean can emphasize where you are round (tummy area) and where you are not (leg area). The same is true for a pear-shaped woman. A skinny jean will emphasize the hips by clinging to them.

So, at the end of the day, it’s up to you. Do you want to emphasize your shape, or balance it out? The answer to this determines everything about the way you approach using style as a tool to get the effect that you want.

Consider these examples.

And now, for the skinny on skinnies. (I totally understand if you are rolling your eyes right now).

First, don’t throw all your skinnies out. Keep the more contemporary-looking pairs (those with fading, distressing, and stiffer, less stretchy fabrics) and pass on the superstretchy dark pairs.

Here, suggestions for picking the best pairs, and styling them in a way that looks contemporary.

Consider The Almost Skinny

Sometimes, jumping from a jegging to a wide-leg can be a bit daunting. I get it. I am right there with you. Enter the transitional jean. The slim straight.

I like to call this the new skinny.

It is less voluminous (read: easier to wear) than other contemporary styles, but still looks fresh and new.

That’s the silhouette I chose for my new Mother jeans (called The Looker). I bought them 2 sizes too big so they would be a little straighter.

A slim straight can be called a cigarette or a girlfriend or a number of other names, but it is essentially a less-skinny skinny. It is slim but not tight. And in a light or medium wash, it is just as versatile as your old skinny but so much more current.

Wear Them Long Or Short

The most contemporary ways to wear your skinny is a little too long, or above the ankle. Ankle length tends to be the most flattering and wearable for most women, but if you have a pair that is a little too long, the scrunched-around-the-ankle look is currently trendy (although it can shorten legs).

Ditch The Jeggings

Separate the skinnies from the leggings-posing-as-jeans called the jegging. These are hard to wear and style, unflattering to most, and have been out of style for some time now.

I say with this love. Jeggings are not your friend. Or mine.

Keep It Current

The best way to make your favorite skinnies look fresh and contemporary is to style them in a current outfit. Save your classics and basics for another outfit, and try a trendy top, a chic slouchy blazer and very modern accessories to update your favorite pair of skinnies.

Look For Updated Details

Skinny jeans in a faded, distressed, or medium wash are going to look much more contemporary than the former holy grail dark skinny pair. The same is true for the pairs with current details like frayed hems, high rises, or split hems. Keep your most contemporary pairs in rotation. And consider DIY-ing other pairs to update them.

Make Them Medium

If you own a pair of skinny jeans in a medium wash, wear them with confidence. This is the wash of the season, and a versatile choice that transitions from summer to fall to winter with style.

Go Black Or White

Black skinnies, and to a lesser extent, white skinnies, can still look fresh and modern when styled in chic outfits.

Upcycle Them

I am not at all crafty, but if I could sew, I would consider turning your old pairs of jeans into your new favorite shorts (this works best with pairs that don’t have a lot of stretch). I have also seen denim turned into doilies, but the benefits of this are dubious. (You know I couldn’t resist that alliteration!).

Your best bet, however, might be in distressing, fading, adding patchwork details, and otherwise updating an old pair to look fresh. If you’ve successfully DIY’ed jeans, let me know. I might feature your creation in an upcoming video. 🙂 Because nobody wants to see any of my DIY projects. #notcrafty

And now I want to hear your thoughts! Do you still love the skinny? Hate it? Ready to try something new? Let me know in the comments!