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5 Wearable Fall Jeans Trends

A flattering pair of jeans is high on my list of must-haves every season. Whether worn with a tee and fashion sneakers or stepped up with a cashmere sweater and blazer…many of my favorite outfits include a great pair of jeans. Each fall I look at the way styles are changing because I like to keep my jeans looking current. Today I’m sharing 5 fall jeans trends for women over 50, but don’t panic!

Trends are slow-moving directions for fashion as opposed to fads that pop in and out of style in the blink of an eye. Trends hang around for many years so if they fit your esthetic and personal style, they’re smart to add to your wardrobe.

Straight Leg Jeans

Madewell The Perfect Vintage High Waist Jeans (Malvern) (Regular & Plus Size)

I’ve been a fan of straight jeans for years and love that they’re plentiful this fall. Don’t mistake these for the mom jeans with a notoriously unflattering shape. Today’s straight jeans have a high rise, are fitted through the hip and seat, and straight to the ankle. They have no flare and they aren’t tight on your legs. These pair well with sneakers, suede boots, and everything in between.  Dress them up with a crisp white shirt and blazer or down with a tee.

See Also – 10 Ways To Wear A White Shirt


Flare or Boot-cut Jeans

Jennifer Connolly of A Well Styled Life wearing casual look with leopard top and blue jeans

Bootcut or flare jeans are one of the most universally flattering styles for every silhouette. I love how the subtle flare helps to balance wide hips, shoulders, or tummy and elongates the look of your legs. If you’re one of the lucky ones who can wear a heel, they’ll also help you look even taller when hemmed to cover your shoe or boot. More on looking taller here.


Wide-Leg Jeans

wide leg jeans
Citizens of Humanity Flavie Ultra High-Rise Wide-Leg Jeans

Some of these look like a flashback to the ’70s 🙂 They often have a high-rise and are full either from the hips down or loose and baggy all over. Proportion is everything for this style and they can be tricky for petite women.

See also – Fashion Tips for Petite Women Over 50

fashion blogger jennifer connolly wearing wide leg jeans

At 5’4″, wide all over jeans would be overpowering so I chose a pair that are slim through the hips and seat, then drop straight down with a wider leg. I’m careful to wear them with a close-fitting top so I don’t look huge all over.

Skinny Jeans

I suspect these will always be in style because so many of us love them. They’re available in almost every wash you can think of. The higher the spandex or polyester content, the comfier they will be. This versatile shape looks great worn with athletic shoes, flats, ankle boots, and tucked into knee-high boots.

fashion blogger on A Well Styled Life wearing Vince Camuto blouse

I bought this pair last month and couldn’t love them more. I can’t wait to try them tucked into my black riding boots!


These continue to be popular this fall and most of the newest ones have a wider leg which separates them from capri pants. They look great with flats in milder climates but how do you keep your ankles from freezing in cooler weather?  Knee-high boots are a natural under wide-leg crop jeans. Tights can add a fun pop of color between the jeans and your footwear or match your tights to your booties for an elongated look.

The other alternative is a sock bootie which seems custom made for cropped pants!


See also –Tips For Looking Stylish Wearing Capri and Cropped Pants

Are you going to mix your jeans shapes up this fall?

If you enjoyed this post please pin it to your Pinterest board.

Thanks for reading ladies and remember to wear what makes you feel confident.








  1. I just turned over another big number. And I want to look my best. I have clothes much like yours, but with no knowledge of how they could be assembled for a classy look. I usually wear the same things the same old ways. Ugh! Thank you for helping and I absolutely love your style. You are an amazing woman!

    1. Happy Birthday, Vivian!!

  2. Denise Thibaudeau says:

    I love your belt in the first picture…..may I ask where you found that? I’m new to your site, so maybe you listed it!
    Also, am very short wasted, wish I looked better in tucked in fashion, Will try with blazer over it.
    Also, high wasted jeans are a challenge with short waste. We all have to modify! ha!
    Thank you for your spot on tips!

  3. I personally feel good in jeans but I like the boot dark one with the Leo blouse on you

  4. Kristiina says:

    Thank you, Jennifer, for the jeans post! And the tips for petites! I find your ideas so relateable and uplifting. Do you have advice for me who am short (5.2) and with heavy calves? Skinny would be fine but for the lower leg area. I am not overweight and am in proportion and small……

    1. I suggest straight vs skinny and of course, a small bootcut would be perfect!

  5. Dianne🇨🇦 says:

    Love most all of your Jean/looks.
    Not in love with the wide leg jeans.
    I must add a crisp new white shirt to my wardrobe this fall.
    Thanks for all your tips, Jennifer

  6. Love the tips, thank you! I’m on the lookout for some bootcuts now but have just bought my third pair of Levi’s skinny high rise jeans before they change the style! Dark denim and black. They’re sooo comfortable and flattering. They’re my go-to staple all year round. And did I mention comfortable 😎

  7. Love the straight leg jeans. You look very put together in all the photos. What if we have longer tops…Any ideas how to tuck longer tops in jeans without bulk

    1. I would try a half-tuck to reduce some of the bulk. Sometimes longer tops just don’t work to tuck in.

  8. Lin
    Love the jeans with the velour blue zipper sweat shirt. My kind of look.
    Looked great on you.
    Love boy friend jean also, can roll the up or leave them down. Very comfortable and look good on short folks like us.

  9. Love all the jeans! You keep us all updated on new fashions!!

  10. Which are the jeans you have on in the first picture coming down the steps and wearing a blue jacket?

    1. They are several years old but interestingly, Jeans with a side stripe are also trending this fall!

  11. I love that first outfit. The jacket especially looks so crisp and sharp with the white shirt. I can’t believe straight leg, hi rise jeans came back. I never stopped wearing them but I’m sure there are small changes. When things come back they come back with a twist.

    1. I’ve always loved straight jeans too…even when they were called mom jeans:)

  12. Love your grey shoes in the top photo!

      1. Love the gray shoes as well. Look totally comfy too. Thanks so much for the great tips, Jennifer.

  13. I love Chico’s pull up jeggings–so comfortable! They really are my go-to jean. I have them in dark blue denim, black and white. I just added a soft dove-grey pair of skinny jeans. They do have a zipper, but still fit close and comfortable like the jeggings. I will never wear that wide legged cropped style. I have ultra skinny calves and ankles, and that wide crop just emphasizes that. I may own one or two of the boot cut jeans, but they fit close to the body. I’m not much for baggy jeans unless I’m slouching around the house.

    1. I’m with you on skinny calves and ankles, wide-legged pants tend to emphasize them on me as well.

  14. Sue Lewellen says:

    In the last 10 years (especially since covid confinement) I have become Humpty Dumpty—an egg shaped body atop skinny legs!! I have to wear pull on jeans for a fit around the middle without being baggy in the seat and legs. I have found that it really takes effort (and shopping) the find jeans that fit.

  15. Not sure about the wide legs but I like all the other styles. I also love the jacket you are wearing in your first picture. Where did you get it, if you don’t mind me asking

    1. I’ve had that jacket several years and pull it out each fall. You can find it here

      1. Johnnie Putman says:

        The jacket in blue was in my Lillysilk cart since I read your blog earlier this week. I couldn’t bring myself to follow thru on the purchase at full price. Today/Wed it is marked down ftom $159 to $99! I signed up for sale info and received another $10 off. Free shipping, no tax. Thanks for the link!!

      2. Amazing!! Well done Johnnie. You will love it.

  16. I have several pairs of straight leg and some skinnies. I think skinnies are here to stay as they tuck into knee high boots so nicely. I wore cropped pants this summer but have not bought the cropped wide leg yet. I think they’ll show off our cute booties perfectly. On the hunt for the perfect pair.

  17. Judy L Brown says:

    I love the look of your first outfit with the straight leg jeans, white blouse, and navy baseball jacket, but I’m only 5’2″ with the thickness around my waist so I don’t like to wear belts. Any suggestions for short, thick grandmas???

    1. Look for tops that are high hip length (wrist level) so you don’t need to yuck them in.

  18. Sharon Satterfield says:

    I love the Madewell straight leg high rise jeans, however, looking for a black color as I already have a nice blue.
    Nice blog.

  19. Janis @ retirementallychallenged.com says:

    I love pull-ups since I never tuck in my top and love the flat front that not having a zipper creates. Have you found any pull-up jeans that are more straight-legged, not skinny?

    1. Look at BetaBrand. It is only available online, but they have skinny, straight, and bootcut, and petite, regular and tall inseams. They have a great denim made from a stretchy fabric. I followed the advice in the reviews and I went down a size in the denim and my ordered my usual size in the dress pant. They fit really well with no sagging or bagging at the butt. I wear only bootcut pants, but the reviews on the other styles are great, too.

      1. Janis @ retirementallychallenged.com says:

        Thank you for the tip!

    2. I agree most are on the skinny side, I will keep my eye out for you Janis

      1. Janis @ retirementallychallenged.com says:

        Thank you!

  20. Great info, thanks! So nice to have choices that we can choose from.

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