Close this search box.

Flattering Jeans for Women over 50

Have you been wondering how those of us over 50 can navigate the new jeans trends? Let me preface this post with this.  The beauty of aging is we can wear whatever makes us feel most comfortable and confident.  That being said, like me, you still want to be stylish and  modern.  Let’s take a look at Flattering Jeans for Women over 50 or some of the jeans trends that those of us over 50 can actually embrace.

flattering jeans for women over 50

There is a myriad of new styles, according to the “experts”, the only clear loser is the Skinny (or so they claim).  After years of being the “drug of choice,” the skinny is supposedly hitting the skids. However, I am still seeing them in stores.  Before you throw the baby out with the bathwater, let’s break down the supposed newcomers and new favorites and which will work for us.  The mom jean, variations of the boyfriend, the straight leg, the barrel jean, the boot cut, and distressed jeans. What to consider when purchasing any of these?

#1 Consider your Proportions

Short Torso and Long Legs

A medium-rise with a longer inseam is your best friend.

Long Torso and Short Legs (that’s me)

Choose a jean with a high rise and an ankle-length inseam.

Here I am wearing the Madewell Viintage Jean.

cindy hattersley in Anthro marled sweater


If you are Short

Go for a wide leg in a cropped length or a girlfriend/boyfriend style where you can turn up a narrow cuff for a more flattering look.

cindy hattersley in pilcro jeans and moto jacket


If you are Curvy

Try a bootcut or a flare to balance out your curves “Fitted jeans that flick outward for extra width at the hem are a good choice for curvy women”

cindy hattersley in banana republic wide leg crop jeans


If you have heavy thighs and or calves

Thicker denim with no stretch is not flattering, nor are jeans with exaggerated washes.

#2 Find Your Most Flattering Rise (this is the distance between the crotch and your waistband)

If you have a muffin top, skip jeans with a low rise.

If you have a short torso and  large breasts choose a medium rise (around 9 inches which will sit right below your bellybutton)

If you want more control (spanx-like) jeans with a higher rise (around ll” will sit at your waist and suck everything in).  Anything higher will shorten your torso and be flat out uncomfortable to wear.

#3 Choose a Practical Length

Stick with ankle jeans or a length that doesn’t drag on the ground. If you’re petite (5 foot 3 or under), a cropped jean (26-inch length or less) or an ankle jean (27- to 29-inch) might work best. I find this true at 5’4 as well.

cindy hattersley in pilcro jeans and black turtleneck


#4 Choose tops that complement the particular jean style

Relaxed jeans look better with a fitted top or a shapely blazer.

A slim or skinny jean looks better with a loose sweater or flowy top.

cindy hattersley in anthro poncho

Here I am wearing the same jeans, the BP turtleneck with the Anthro poncho.

cindy hattersley in anthro poncho with Beau


I admit it, jeans have been my wardrobe staple since my teens.

Here are some articles you might enjoy

Best Jeans for Women over 50 2021 Woman’s World

Read  this article from Slate (basically, anything goes wear what you love)

Most of the articles from the fashion police are a bit contradictory.  I think you will find humor in them if you have the time to read:

Who What Wear Five Denim Trends That are Hitting Their Expiration Date in 2021

These are the Jeans Everyone Will Wear This Year

Elle Best Denim Jeans Styles

This blog post from Jo Lynne Shane is particularly well done.

One look I will not be embracing is the mom jean. I was a mom in the ’80s and wore the so-called mom jeans. I have a small waist and a large “booty”.  That style from the back is not very attractive to me. Are there any new styles you would like to try? If you aren’t totally confused already the Zoe Report’s report advises, “start with the fact that there is no wrong style to try.” Wear what you love and feel comfortable in. FYI Levis best-selling jean…the 501 (sound familiar?)

cindy hattersley in BP red blazer


You might also enjoy reading my Spring Jean Styling Post with Jennifer here.  I featured a couple of the same styles.

Thank you for being here and reading Flattering Jeans for Women over 50. Now let’s see what my two stylish friends are wearing.  I noticed on Instagram that Kim tried on one of the same pairs of jeans that I have shown here.













Reader Interactions


  1. Juliet says

    Loved this series topic so much, Cindy. I won’t be embracing the mom jean either, but I do love the cropped flares. Over the weekend you ladies inspired me to try on all my jeans and I weeded out 10 pair. Yay, me. Love your red jacket. xo

    • Cindy Hattersley says

      Hi Juliet

      Jeans are my uniform…I admit it!! Those mom jeans aren’t for me…I can’t believe I ever embraced them, so unflattering on most!

  2. Liana says

    You look gorgeous in all pictures. I have to admit that I’m having a hard time to part with my skinny jeans. Having, wide hips and smaller waist, the stretchy denim of skinnie’s had been the only style that molds onto my body without gaps and buckling knees.
    I have cropped mines to a classic pencil length in the hope to wear them for another season or two.

    • Cindy Hattersley says

      Hi Liana

      I agree with the issue of the gaping knees. We must have similar builds. I think some version of skinny will always be popular!!

  3. kim says

    Cindy you look so good in all these styles, and especially I love the painter pant and the wide leg on you. You did a super job of breaking this down better by body type. I feel like I have all the issues… LOL. Thank you I am looking at some of these styles now I haven’t seen before. You are so right about balancing the tops too with the shape. Always a joy to do this with you ladies. xo Kim

  4. Wren says

    Thanks for a good distillation of jean styles. I really like your red blazer from BR but I see it only comes in red and yellow which won’t work for me. The red is a good color on you and is the perfect length.
    I have kept 2 pair of Gap boot cut from so long ago that they are measured in size (6) rather than waist measurement. They still fit and I think I’ll wear again when the weather calls for boots. I don’t usually hang onto clothes but glad I did in this case. I’m convinced that the only reason fashion trends come and go is to get us to part with our money! But I’ll still be wearing my skinnys………

  5. Patricia G McGrady says

    Another tall girl here! 5’10”. What I think I want is something between a skinny and a straight. I use to call them cigarette jeans. I’m SO over skinny jeans. Where can I find them?

    • Laura says

      I found some “cigarette jeans” from 1822 in black and a dark denim. Nordstrom and also the 1822 site. They have a button/zip fly and I LIVE in them. But they are the super skinny ankles. I will take anything that is long enough! Tall girls rule!

  6. Sarah says

    Oy, it all just makes my head hurt! I’m a pear (or as Sarah rather more nicely puts it, an A) but isn’t “curvy straight” an oxymoron? LOL, I’ll sort through it all when I can actually venture into a dressing room again. Thanks, Cindy et al, for doing the homework for us!

  7. Laura says

    Any hints for someone 5’10” and 135 lbs? I try to find 34” inseams (difficult) and unless you want to spend $150 for jeans you’re out of luck. I am used to having “high waters” (!) but would like to be able to wear heels or boots without looking like a fool.

  8. dianne says

    I just bought a pair of the Rag and Bone Miramar full leg jeans. Silk like – sort of anti jeans but so flattering and soft and liquid-y. They are on the long side but I find them fun and comfortable and modern.

  9. Gray says

    Just put two pair of Pilcro jeans in my cart at Anthro – wide leg and icon boot cut. I have skinny, straight and boyfriend. Agree with you – wore the mom jeans the first time in the 90’s. Am having a love affair with wide legs and palazzo legs these days.

  10. Marianne says

    Cindy, where, oh, where did you get the sweater in the first picture with the Madwell jeans and black hat? The link is for a similar one, Howe that one is gorgeous!, thanks

    • Cindy Hattersley says

      Hi Marianne

      I fixed the link. It is also from Anthropologie. I will email it to you in case you don’t catch this…sorry!!

Edit Content
Click on the Edit Content button to edit/add the content.
• powered by chloédigital