7 Chic Denim Trends you can Wear After 50 Confidently

ByCindy Hattersley Hours Posted on Hours Updated on
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Why does denim hold such a special place in our hearts? It is the perfect blend of practicality and personality. Denim is a strong, long-lasting fabric that can withstand wear and tear, molds to our bodies and only gets better with age, just like us. Let’s join my blogging pals and chat about 7 Chic Denim Trends you can Wear After 50 Confidently.

I am constantly asked about wide leg pants and who can wear them. If you love them embrace them. I personally think almost anyone can wear them. You can read the post I wrote three years ago Wide Leg Pants do you Love them or Loathe them here. I do think they are more flattering on me if I wear something more fitted on top like this great lightweight cashmere sweater from Mersea. These jeans have a more flattering high-waist You can wear them at the ankle or longer if you can still wear heels.

WIDE LEG JEANS

I get more questions about wide leg pants than all of my questions put together. People ask if I am a petite can I wear wide leg pants? I am overweight, will they make me look bigger? No, as long as you find a flattering pair that suits your body type.

Here I am wearing a pair with front patch pockets from Anthropologie. I think this high rise option is very flattering as it slims the tummy, thighs and hips and there are no side pockets to pooch out, providing a lean look. I styled it with a dreamy lightweight fitted cashmere sweater from Mersea (love this).

Wide leg jeans with lightweight cashmere sweater.

These jeans are from H&M. They are more of a straight leg that I rolled up for summer. I would roll them down and wear them with boots in the winter. I am not a big fan of those wide legs with the giant cuffs. I know they are “on trend”, but they look like they need to go to the tailor in my opinion.

black linen shirt with H&M jeans and janessa leone straw accessories

Shop the Jeans Looks

DENIM DRESS

Denim dresses strike a perfect balance between casual comfort and chic style. I purchased this white denim Rory dress from Frank and Eileen. The blue or black denim would be fun as well. They also have an above the knee version for those of you who can still wear that look. This dress can be dressed up or down as seen in my post Five Stunning Ways to Style a Shirt Dress at Any Age.

Frank and Eileen shirt dress with red linen shirt and colorful jewelry
Frank and Eileen Shirt Dress styled with Mersea Sweatr and Sneakers

Shop the Denim Dress Looks

DENIM ON DENIM

Rocking double denim can create a cool, fun look. You can also mimic the look of a jumpsuit without having to deal with the dreaded one piece. I have to be careful with white jeans. If they aren’t thick enough I get the “sausage look” as my daughter would say.

White Denim jacket with white denim pants and sneaks

Here I am wearing a pair of Madewell wide leg jeans (no longer available but similar here) with a jean shirt I have owned for years.

Over 50 Style Blogger Cindy Hattersley in J Crew Chambray Shirt and chambray crops

Shop Denim on Denim

DENIM JACKET

The basic design of a jean jacket – with its button front, and pockets – is simple and flattering on many body types. This classic design transcends trends. From washes and distressing to cuts and details, you can find a jean jacket that reflects your own personal style. Vintage shops have great lived in versions.

I have had this Gap denim jacket for years. I don’t usually wear “chiffony” fabrics but I like the juxtaposition of the denim with the girly skirt.

cindy hattersley in Anthro maxi and gap jean jacket

I found this Ralph Lauren jacket on eBay and Mermade Brooklyn customized it for me last year. Meredith is super creative and can really up a jean jackets game.

cindy hattersley in polo ralph lauren/mermade brooklyn jean jacket & bryn walker linen pants

This jean jacket came from the Gap as well. I have also owned it for several years. The dress is from Hannoh Wessel but no longer available. I linked similar below

white dress and jean jacket

Shop Denim Jacket Looks

DENIM SKIRT

A denim skirt is like a great pair of jeans they just get better with age. This patchwork skirt with the ragged hem is from Etsy. I paired it with a linen shirt and sandals for a casual look. You could throw these pieces in your beach bag and toss them on offer your swimsuit.

Patchwork Jean Skirt, linen shirt, sandals, a straw bag and hat.

This denim skirt with the stitched down pleats from Zara (sold out but similar linked below) has a more refined silhouette. This skirt could go to work and be dressed up with a blazer.

zara white shirt and zara denim skirt

Shop Denim Skirt Looks

DENIM SHIRT

Denim shirts have always been a wardrobe staple for me. Their timeless style and effortless durability, makes them versatile wardrobe staples. The more they age the better they look. This white denim western shirt came from Banana Republic Factory. I wear it all the time.

cindy hattersley wearing Eileen Fisher and Banana Republic Factory
Over 50 Style Blogger Cindy Hattersley in BR Factory Eyelet Skirt & Shirt

Shop Denim Shirt Looks

DENIM JUMPSUIT

A denim jumpsuit is like a one and done dress. Add pretty accessories and you are out the door.

Anthro Colette Weekend Jumpsuit

Shop Denim Jumpsuit Look

When it comes to jeans wear what you are comfortable in and whatever style of jeans flatters your particular figure. Other than skinny jeans, and might I say those cuffed options that look like they are headed to the tailor, boot cut, straight jeans, boyfriend jeans, cropped jeans, high rise and mid-rise jeans all work this season.

Did you ever give up your jean jacket, denim shirt or jean skirt? Are you wanting to rock a denim shirt dress or attempt denim on denim? Go for it and enjoy! Thank you for reading 7 Chic Denim Trends you can Wear After 50 Confidently. Now let’s pop over and visit my friends and chat about what works and doesn’t. Let’s get the conversation going.

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35 Comments

  1. I love everything especially the white on white (denim jacket / dress). Great post!

  2. I think I found your soft worn denim shirt at Goodwill!😄
    Love your pairings, inspirational!
    The straw accessories are so flattering.
    Ty so much & will be following you!

  3. Fantastic post, Cindy!

    I love seeing your denim collection. Like you I enjoy collecting denim items. When the cut and the fit is right, they are forever pieces for me.

    You styling and accessories paired with denim are exceptional at any age.❣️

    Rosemary

  5. I love your style. Will most definitely will try out some of them. Thanks for sharing.

  6. You have such a great sense of what looks good on you! I’m almost 80 and still love my jeans. Having a hard time giving up my skinny-ish pairs, and finding the right ankle-length straight leg. Also hard to find shorter tee’s to go with the wide-leg jeans. I’m short waisted so regular tees fall too low. I prefer tees to shirts. Any ideas? Hugs.

  7. Cindy! You’re right! Denim gets better with age! I love those wide leg jeans… H&M? Really? And that maxi skirt!! You have the best style!!

  8. Cindy, I absolutely love your style. Everything comes together so perfectly. Thank you for sharing.

  9. Love seeing you in all these denims. I have no intention of putting aside my denim even though I am 70. I tried to explain to a friend, who just turned 80 and doesn’t wear denim and thinks I shouldn’t too, that I grew up in the late sixties/early seventies when denim was all we wore and it just feels right.
    You’re rocking all these looks and making me reassess wide leg jeans.

    1. Hi Joanna

      I am with you! Denim is my closet staple. I will wear it until I die!

  10. Great post Cindy! Thanks for extolling the virtues of Gap denim jackets. I have a Gap denim western shirt that’s 20 years old. I take it on all trips—headed to Paris with it today!

    1. Hi Karen

      I think the Gap jackets are the best! Classically styled and well made. I had a gap western shirt that I gave to the Goodwill because it was so worn…I wish I hadn’t!

  11. Hi Cindy,
    You look so good in all of these outfits! I’ve had my eye on those anthro pants in cream, but couldn’t justify the expense, because I definitely don’t need a thing. Then I found an almost identical pair at Macys for 1/4 the cost, so of course I bought them. They need to be hemmed, and I can’t wait to wear them!
    I have one of each of these items, I don’t think I will ever feel too old to wear any of these timeless, classic pieces!
    Xo Heidi

    1. Hi Heidi

      Isn’t it fun to find a bargain? That is why I love all the resale outlets. Who wants to pay full price if you don’t have to!!

  12. Cindy, you look fantastic in the white Lake Jean. That first style from anthropology is so good on you. I also like that wide white jean!! I think I’m gonna order that Anthro one! Those denim skirts are also super cool! Fun post today..and you make everything look so good.

    2. Hi Kim

      I just love denim… never gets old in my book!! You and Annie can rock those wide cuff numbers. I would look awful in those!!

  13. Thank you Cindy l love the way you put hi and low end pieces together to create a look, l bought a new white denim jacket recently on sale and l completely forgot to check out Gap so thank you for reminding me. My daughter, who is tall, looks amazing in jumpsuits. Look the look !

    1. Hi Francesca

      I bet your daughter looks fabulous in everything! Ahhh to be tall!

  14. can you share where you got the backpack purse that’s shown with the rag patch denim skirt. ???
    love all your ideas with denim , I finally got a denim jack for myself and your ideas will help me feel confident in wearing it.
    thanks for being so stylish and sharing

    2. Hi Pam

      It is linked in the shop the look widget. I love that bag!! It can be worn over the shoulder or as a backback which is fun!!

  16. Hi Cindy,
    I’ve had luck with Amazons woman’s denim shirt dress. Front buttons, frayed sleeve s, comes in multiple colors. The larger sizes are comfortable, yet stylish to wear over skinny jeans or ?

    1. Hi Ann

      I will check the Amazon dresses out. I am reluctant to link to them unless I hear good things!

  17. All great classic looks Cindy! I especially love the denim on denim, I am a huge fan of this combination!

    1. Hi Noelani

      Thank you so much for joining us. You do such a great job!

  18. I love all the ideas presented in this article. I am petite, so snug fitting is better for me and I get lost in loose-fitting long pieces. Thank you. . .you look mahvelous dahling!

    1. Hi Lynn Anne

      I completely understand. I walk a fine line as well. If they are too baggy they look like they are wearing me. Especailly since I no longer wear heels.

  19. I do love the denim on denim look! Love that jumpsuit on you so much! Inspiration to get me dressed for the day!

  20. Love this post, Cindy — you read my mind about denim AND the wide-leg pants issue. Everything you showed here looks fabulous on you, and you answered some questions I’ve had about how to style the wide crops. I am finding (for myself) that it helps when the wider pants “skim” past the heavier areas of my hips and thereby camouflage the “saddle bags,” as I call them — especially if I am not wearing a tunic-length top. In that case, the flow, wider styles are actually flattering. Also — as you point out, the cropped (shorter) tops give better balance to the wider pants. Bravo and thank you, Cindy!

    1. Hi Cindy

      I completely agree. I have the same issues as you. Thanks for weighing in. I love your blog by the way.

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