Wearable Modern Jeans For Women Over 50
It’s no secret that I love a great pair of jeans. A peek into my closet reveals them in all colors and washes. More often than not, my casual lifestyle has me reaching for a cozy sweater and some denim this time of year, so today, I’m sharing a few ways I like to style modern jeans for women over 50.
I’m back with my friend Cindy for our monthly Style Over 50 edit, and we’re talking about jeans.

If you check the internet, you’ll see lots of articles exploring if we’re too old to wear jeans after 50. What do you think? At what age should you stop wearing jeans?
I think we should ditch wearing jeans whenever we feel we’re ready. If you’re unsure, ask yourself these questions:
- do they still fit my lifestyle?
- do they send the message I want my clothes to send?
- are they comfortable?
- do they make me feel like myself?
Jeans come in so many silhouettes, sizes, washes, and leg shapes; there is a great pair of jeans out there for any woman who wants to wear them.
So let’s look at some modern styles and ways to wear them.
Straight Leg Jeans
A classic straight-leg is my current favorite. They’re looser than a skinny but not sloppy. They are usually fitted through the hips and drop straight to the ankle, giving nice room in the thigh area.

Petite Jeans
If you’re petite, shop your bootcut and flare jeans in the petite department. The act of shortening them removes some of the width from the bottom of the leg, which can ruin the shape. You can find great petite jeans at J. Jill, Loft, Talbots, J. Crew, Madewell, Banana Republic, and Anthropologie.
Related – How to Shorten Your Jeans and Keep the Original Hem
Flare or Bootcut Jeans
Boot cut jeans are universally flattering on all body types. Their timeless silhouette looks great with a flat shoes, low heels, or, not surprisingly, booties. They provide a great balance for all body shapes and add balance for wider hips, broad shoulders, or full tummy. These can be snug or skim the thighs and then widen from the knee down.

Skinny Jeans
Are they dead? Should you care? It’s no secret that the skinny jean trend has been phasing out over the last few seasons. I expect they’ll remain a wardrobe staple for many women because the tight calf makes them the best jeans to tuck into knee boots. Are you wearing skinny jeans?
Versatile Jeans

I find dark-wash denim easier to dress up than lighter washes. How about with a silk blouse and pearls? This machine-washable silk blouse was a delight to find. I’m not sure how Quince manages to produce such high-quality pieces at the prices they do, but I’m thrilled with them. This blouse comes in twelve colors. They also make a notched collar version here that’s in my cart in coastal pink. The petites were too short in these wide-leg jeans, so I bought the regular length. The website shows them really short, which I think looks sort of goofy.
See also- What Length Should Your Pants Be?
High-Waist jeans
These sit at or above your natural waistline. High-rise jeans are great for camouflaging tummy bulges and preventing muffin top. If you have a short torso and/or are petite, you may get the same benefit from mid-rise jeans. Low rise is currently out of style, but I am hearing some nasty rumors of their return.
Canadian Tuxedo

We can’t talk about jeans and not remember the Canadian Tuxedo. Popularized by Bing Crosby, wearing double or more denim pieces in a single outfit will be a big trend going forward into 2023. I’ve always loved the look and simply vary the wash, so I don’t look like I’m wearing a suit…although I have nothing against that either.

I love, love these Loft jeans! They’re so affordable and have everything I want. A high-rise, slim through the hips, has a nice wash for spring, a finished hem, and they’ve got enough spandex to be super comfy. I tried on the petite, which was a smidge too short, so I bought the regular and will wear them with these block-heel boots or hem them if they don’t shrink.
Affordable Jeans
I must be a reverse snob when it comes to jeans. I’ve had very expensive pairs that ended up with twisted seams after the first wash. I’ve also got jeans that are super affordable and look like a million bucks. I say buy what fits the best in the budget you can afford.
Extra tips about jeans
- The lower the back pockets, the longer and lower it makes your butt look.
- Medium-wash denim will be more timeless than trendy washes
- White jeans are in style all year
- Back-gapping in the waistband is common for curvy women and can be helped by a flat belt like this.
Now let’s see how Cindy at Cindy Hattersley Design is styling her jeans.
Thanks for reading, and remember to wear what makes you feel confident.
GQ Recommends Dual stimulation gets you the best of both worlds. By Kate Sloan June 5, 2023 All products…
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