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How to Rock Your Jeans with Confidence after 50

Hi Everyone. Jennifer and I touched on this topic a couple of years ago, so it is time to update and rewrite this post. My jeans are a wardrobe staple, particularly this time of year. You can dress them up with blazers and wraps, or down with a a sweater and sneakers. Currently practically anything goes with jeans styles. There are so many shapes, rises, and washes available it can be overwhelming. When choosing jeans make sure you purchase the right fit, fabric, wash and proportions to suit your body type. Let’s talk about how to rock your jeans with confidence after 50.

I am glad that jeans have gotten a little looser.  I think it is flattering to more figures. For women over 50, a high-rise jeans can be more flattering. This style of jeans helps to elongate the leg and create a long and lean look. Cropped lengths suit those that are five foot three and under (no tailoring).

In this photo I am styling my KUT straight-leg jeans with a beautiful Lysee fringed blanket coat, BR scarf belted with my Native American concho belt (you can find similar on eBay here), and my comfy Gentle Souls boots. The Lysse blanket coat is soft and cozy.  I had a similar version last year in black and brown, but this all black version is really versitile. I love the simple fringe detail down the front. 

Boyfriend jeans, belted scarf and long coat

Here I am wearing the same jacket with the BR turtleneck, my inherited Don Lucas necklace, Kut jeans and Gentle Souls ankle boots.

Lysee Coat Kut Jeans

SHOP THE LOOKS

I assume that most of you who’ve been living in skinny jeans have tossed them by now.  Many jeans have sculpting properties built into the design to help contour our particular silhouette. You can choose from high-rise, low-rise, wide-leg, boot cut jeans, boyfriend jeans and more. They can be found in short, medium and long lengths, cropped ( the ankle pant should be at a length to highlight the slimmest part of your ankle) or puddled (not recommended for our age due to the tripping factor).

Wardrobe Oxygen has a great article on the correct hem length for all styles of pants here.

I am wearing Kut from the Kloth’s wide leg jeans in this photo with two indespensible Eileen Fisher separates, her merino tee and wrap with my monogrammed velvet birdies (another classic). I am on a hunt for a longer pair (that doesn’t puddle) for winter.

Wide Leg Jeans with Eileen Fisher tee and wrap

Here I am wearing the indespensible Eileen Fisher Merino tee with the same KUT jeans and Birdies.

Kut from the Kloth Jeans Eileen Fisher Merino Tee

SHOP THE LOOKS

J Jill recently brought back this favorite boyfriend jean of mine.  Here I am wearing it with a BR utility vest no longer available similar linked below, a white shirt and gigi pip hat.

banana republic utility vest, j jill jeans, athleta shirt

SHOP THE LOOK

If you want a jean that looks a little more polished like a pant but is very flattering you might like the Lysee Payton Wide Leg Crop. It has a pull on waist, and is soft and comfortable.

I paired it here with the Lysse Camper shirt (slimming and no iron-great for travel), a gigi pip hat and camo birdies.

Lysee Wide Leg Crop Jean with Lysee Shirt Gigi Pip Hat

I paired the same Lysse jeans with the great BR lightweight t neck, vivaia shoes and the wonderful Quince cashmere sweater.

LYSEE JEANS, QUINCE CASHMERE, BIRDIES, RAG AND BONE BAG

SHOP THE LOOK

I love this cozy Rag and Bone Wrap, worn with the Lysse jeans, and camo birdies, and Lysse camp shirt.

rag and bone wrap lysse jeans

SHOP THE LOOK

Don’t be afraid to “wear what you have”.  I am wearing my beautiful Quince cashmere throw as a wrap. Tie it around your neck and tuck it in for fun.  Styling it with Kut jeans, a favorite pair of Artemis Design Co slippers and a Gigi Pip hat.

Quince Cashmere throw Kut Jeans

SHOP THE LOOK

Here I am wearing the same KUT jeans, a Ralph Lauren military jacket (no longer available but similar linked below), gigi pip hat and born loafers.

Ralph Lauren Military jacket, KUT jeans, gigi pip hat

SHOP THE LOOK

Not all of the latest and greatest jeans are worth trying. When shopping for denim make sure you purchase a pair of jeans that is the most flattering for your body shape. Current styles that are more flattering for those of us over 50 are the boyfriend, wide leg, and flare jean. A darker wash can create a dressier look as well as a slimming effect. If you are going to buy a trendier look, go for a more inexpensive option. Don’t be afraid to spend money on a nice pair of jeans if you wear them often. Avoid overly long jeans that puddle, and “mom” styles that puff at the hips and waist, or barrel jeans that curve out at the sides.

Further reading:

Find the Perfect Jeans for Every Body Type

AARP Best Jeans for Women 50+ Women

I hope you enjoyed How to Rock Your Jeans with Confidence after 50. Do you have a brand or pair of jeans you love? I am on the hunt for a longer wide leg pair.

 

 

 

 

 

Reader Interactions

Comments

  1. jess says

    WOW! How cool that I found your blog! Sometimes I can not find the right size clothes (especially pants) so tailoring is also a solution for those who are seeking well fit and nice quality. What is more, these days you can order custom things online from Coco Mel or Dressarte Paris or just to visit a local tailor. Where do you mostly get your clothes from?

  2. Kathy says

    I’ve lost enough weight since last winter I’m replacing my jeans. Trying to find a pair of jeans to wear with boots that don’t look like I’m ready to go work on a ranch. Your suggestions are very helpful. I’ve always just worn Levi’s but they’re not doing it for me anymore.

  3. andi says

    Cindy , you like KUT denim . i wanted to know obout the fit? are they tru to size ?i found a few pairs in their final sale offerings and need a bit more confidence to make a purchase. any help would be great.

    • Cindy Hattersley says

      Hi Andi

      Yes they do. I wear a 25 in the Rachel and the Meg. They always seem to be true to size.

  4. Pam says

    Cindy, you have really inspired me to “shop” my closet. you are so stylish i have to ask your help and advise on belts, necklaces and accessories . Being a full figure 2X, any guidelines to wearing such accessories , sometime i but on a belt and just shake my head because i feel i look silly. So i would love to hear your suggestions

    • Cindy Hattersley says

      Hi Pam

      I know how you feel. I am not looking the greatest in belts these days as I have gained a few pounds that I need to lose. I think a tunic length sweater with an interesting scarf might make you a little happier. You have given me a good idea for a post. Keep those ideas coming!

  5. Cara says

    It’s hard to find jeans that are all cotton and I only shop second-hand so choices are limited. Recently I’ve had some luck with children’s sizes. I’m 5’1& 1/2″ and weigh 105, so small… I also notice that ALL clothing sizes are seriously screwed up. When I was in high-school and weighed 98, I wore a 2 or a 4. Now I wear a zero or 2 (which, depending on the brand, can also be too large), or girls’ 14! And obviously I haven’f gotten smaller!

    • Cindy Hattersley says

      Hi Cara

      You are absolutely right. The vanity sizing has gotten out of hand. I tend to like jeans that are cotton with a bit of lycra for stretch. They are more forgiving. Vintage levis are huge here in Ca. The vintage shops are loaded with them.

  6. bonnie sachs says

    you have the BEST.STYLE.EVER. this coming from a gal who prides herself on her style. truth be told, i have at least half a rack of jeans. all different, whether in style, color or length! i am learning from you!

  7. Prue Batten says

    You style everything so well. Fantastic unique accessories that really sell the outfits. You look amazing. I am so envious or your wraps and hats!
    Jeans are a staple for me and I still have a couple of skinny jeans and leggings. Depending on how they’re styled, they look quite classic.
    I’m not a fan of high rise so much as I love my belts and belting high seems to always make an older woman’s tummy quite obvious, whereas a midrise has the belt sliding across the tummy. I’ve managed to keep my waist and regular-sized hips into my 70’s, so I guess I’ll stick with what suits me and not err to what fashion houses sell too much.
    One thing though, I can’t understand the fashion fascination with a raw hem. It’s so easy to hem jeans and they look so much classier with beautiful shoes. But it’s all personal I guess.

    • Cindy Hattersley says

      Hi Prue

      Ha the raw hem! I love them because I am not a seamstress. It costs a fortune to get jeans hemmed these days! I understand how many do not care for the look. It is definitely not as polished.

  8. Barb L says

    I live in jeans most days, and your looks are fabulous! Love the fringed coat, utility vest/military jackets and all the wraps. I will check out the Gentle Souls ankle boots. My well loved ankle boots were put to rest after last winter so searching for a new pair. As always, your looks are inspiring.

    • Cindy Hattersley says

      Hi Barb

      I have those boots in two colors and I am thinking about purchasing a dark brown suede. I have a bunion so my choices are limited.

  9. Nancy says

    Another great post, what great inspiration you are! I have to ask, what is the clip you have on your Camper Shirt by the neck collar? Is that a hair clip re-purposed or ? And how can I do that?:) Thank you so much for your blog

  10. Joanna says

    I live in jeans. They suit my casual, retirement lifestyle. My favourite type is straight leg. I find they go with most footwear. In the warmer months I wear cropped in light wash but fall back on longer, dark indigo and black for fall/winter. I find you can dress them up with a nice top. I just bought a pair of slim straight leg in grey.
    All my skinnies were donated. They didn’t really suit my body type (slight pear) anyhow but I made them work because they were trending. I’m happy they are considered out.

    • Cindy Hattersley says

      Hi Joanne

      Jeans suit my lifestyle as well in the fall winter and spring. I like a straight leg too. I am glad to see the skinnies go as well!

  11. Sydney Haskell says

    I am a true petite woman at 5’2” and 140 lbs. My waist is disappearing and made finding jeans hard for years. Pamela Lutrell showed me Chicos wide leg jeans and trouser style jeans. I bought 3 pair in 2P which is a 12P. They fit me perfectly even when sitting in a vehicle for 8 hours in the backseat next to my rescue Havanese 9 year old dog in her booster seat. I love the comfort and look of these jeans.

    • Cindy Hattersley says

      Hi Sydney

      Thank you for sharing! Pam has great advice. We are planning to do a group post. We need to get on that.

  12. Cathy says

    Six months out of the year it’s cold and wet where I live. Yesterday it got all the way up to 48 degrees and we had 1 1/4″ of rain! I’m retired and spend a lot of time at home and need jeans that cover my ankles and the heavy socks I wear to keep my ankles warm. After a couple years of not finding anything on the market I’m thankful that recently I’ve found jeans at Talbot’s that meet my criteria.

    • Cindy Hattersley says

      Hi Cathy

      I wear a lot of boots in the winter. I understand what you are saying about keeping the ankles covered! I will check Talbots out!

  13. Nancy says

    I recently started following you and love your style. I’m 5’8” and have found the Nicole Miller brand of jeans that Marshall’s and TJ Maxx carry, fit me well. The styles change frequently too, keeping up with current trends.

    • Cindy Hattersley says

      Hi Nancy

      Isn’t it great when you can find a brand at TJ or Marshalls that works? I love them!

  14. Rita says

    Thanks for a great blog post. I still like skinny jeans with boots & long sweaters. The fashion industry is deeming them passé but we don’t have to follow their dictates. It is fun to try new styles though and thank you for showing them to us.
    How do we get to Jennifer’s Blog??
    Thank you.

  15. Paula says

    You are such a style inspiration Cindy; l love all your looks, especially the layers. While layers are my thing, it is a rare day in SoCal that I can pile it on! My signature jean is a demi-boot crop, sometimes called a kick flare, which is flattering and seems to elevate any outfit. I haven’t seen it mentioned here, so thought I would add a link. J.Crew and Gap do it well. https://www.jcrew.com/p/womens/categories/clothing/denim/demi-boot/9quot-demi-boot-crop-jean-in-dark-worn-wash/AB376

    • Cindy Hattersley says

      Hi Paula

      I love a demi flare but they aren’t flattering on me. I have big thighs and they tend to accentuate the negative. I sure love them on others though.

  16. Wren says

    I was thinking how beautiful the backgrounds are in every new picture. They almost steal the show! It’s kind of unbelievable that there are 2 stores in little SLO that carry KUT and they are fairly priced. I did well buying new white jeans from that brand for summer, now I want a pair of boot cut in a dark wash. I still have my skinnies too. You know what they say, fashion just repeats itself.

    • Cindy Hattersley says

      Hi Wren

      I love that brand. Currently, KUT it is the only brand that fits me well overall. They are fairly priced to which I like! We need to get a date on the calendar!

  17. Julane borth says

    Hi Cindy I went to the Lysee website to look at the camp shirt you wore with the jewelry at the neck. What color do you have on? I like that color with your hair (mine is same color). Thanks for letting me know the color.

  18. Liana says

    Your picture by the arbor in yellow snd red looks so beautiful. Most of what I own is skinny jeans and I still should be wearing them for awhile. This year I have bought several knee high boots. And for my thick calves , the best jeans for tucking in winter boots are still the skinny’s. Currently loving the straight leg high rise jeans.I use to be a Lucky Brand jeans loyal, but ever since they’ve got bought out, their current fit no longer suits me

  19. Elizabeth@pineconesandacorns says

    Cindy you always look so stylish! I think you might need to rename the blog to Cindy’s Effortless Style for Home, Life and Fashion
    I personally hate to wear jeans. I do wear them occasionally but I have a big butt, I have had it my entire life,( I was a Kardashion before they were born )and I have a small waist, consequently it is hard to find pants/jeans that fit. If I do wear jeans I like to wear cropped/to my ankle style either wide leg or rolled.

    Thank you for the roundup! Have a wonderful weekend.

    • Cindy Hattersley says

      Hi Sarah

      Thanks so much pal. Those kantha coats are the best! Two looks in one!

  20. Karen B. says

    Cindy,
    Great post as usual. I have purchased and enjoyed quality from both GAP and J. Crew jeans. I like the fit of the GAP jeans and they have washed and retained their look for years for me. I air dry them once washed. The J.Crew jeans were also great, but do not fit me as well as the GAP skinny jeans.
    I love the jackets you’ve shared.
    xo,
    Karen

    • Cindy Hattersley says

      Hi Karen
      I agree about Gap and J Crew and Madewell jeans. I have yet to invest in expensive jeans. However, I think investing in a good pair of jeans is money much better spent than buying an expensive dress that is worn once or twice!!

  21. Heidi says

    Hi Cindy,
    All great looks on you. How I wish I could wear a size 25!
    I have so many jeans in all styles, skinny, wide, boot, short, long, dark, light, black, blue, white, lightly distressed and not. . I have to look closely when I pull them out of my closet to make sure they are the pair I want! I agree that anything goes right now, but I can not understand those super distressed kind with the holes going all the way up each leg. What’s the point? Just wear shorts instead! Anyway….
    I do enjoy your fashion posts, keep em coming!
    XO Heidi

    • Cindy Hattersley says

      Hi Heidi

      I only wear a 25 in the “loose” jeans, have to size up when they are skinnier if you know what I mean!! Since I have a smallish (compared to the rest) waist, I can wear a smaller size in the baggier version. I am going through my jeans today and pitching those that no longer fit!!

  22. dianne says

    I am obsessed with NSF jeans and pants. The Nori jeans are so so so comfortable and fit so cute! They are made in California ( a bit spend but when you find a good jean, buy it!).

  23. Sandra Sallin says

    Jeans? Are you serious? I’m terrified to try them on. I do love the white ones though. But I can’t believe my eyes getting used to the look of the blue jeans. Isn’t that funny? Suddenly I just like the white. Well those skinny jeans that are not supposed to be cool look great. But I think I’m going to look for white jeans. If I ever go shopping again.
    Yep, white it is. That means I don’t have to try on my old ones which probably will not fit.

    • Cindy Hattersley says

      Hi Sandra

      Our shopping habits sure have changed haven’t they? I too wonder if we will ever really shop in stores again?

  24. Linda Fant says

    I have embraced the idea of skinny jeans being. passé, and have moved on to straight jeans in various forms..rolled up or ankle. I like how they still give a slim profile, but with more breathing room😁. Am on the hunt for a good flared Jean like I wore in the 70’s. They hugged the hips and upper thighs, with a gradual flare to the floor. I lived in those for many years. Thanks for your suggestions and photos..loved this post❤️

    • Cindy Hattersley says

      Hi Linda

      I agree with everything you said. You might like the BP ones. They are made well and hug the hips! I am over the skinnies too.

    • Cindy Hattersley says

      Hi Mary Ann

      I can’t imagine not wearing jeans. I have worn them less during the pandemic reverting to yoga pants, but they are working their way back!!

    • Cindy Hattersley says

      Hi Leslie

      I am so sorry that is what happens when I am burning the mid night oil. Please hop over and visit Jennifer. Her post is filled with useful information about the new styles. She is the expert not me!!

  25. LA CONTESSA says

    GAP clothes never fit me..Maybe because I was a bit on the chunky side!
    As you know I have ONE pair of jeans from SOFT SURROUNDINGS from a MILLION years ago…….they are my GARDEN OUTFIT!
    SO, ZERO INPUT FROM ME TODAY!

  26. Jennifer says

    I love your raw hem jeans! I’ve got one pair but apparently need another. They look so modern on you. I’m used to buy all my jeans at Gap but haven’t in many years so I will have to check them out again. As always you look amazing!! Xx

    • Cindy Hattersley says

      Hi Jennifer

      I really like the raw hem jeans too for some reason. Especially for summer, it just seems more laid back. Thanks for doing this with me. So sorry about the broken link!

  27. Carol says

    You do a wonderful job styling your clothes and it is so helpful to see how you mix old with new. Because of your posts I am “shopping my closet” regularly. I am pleased that so many styles are available in jeans and I am delighted that high-waist is an option now.

    • Cindy Hattersley says

      Hi Carol

      Yes hip hip hooray to the higher waist. Those low riders were definitely not for us!!

  28. Diane says

    Once again, you’ve knocked it out of the park! Jeans “looks” that are simple, stylish, youthful but appropriate! I love posts like this with easy styling ideas. I do have a question, though. You say you are wearing a size 25, and only for reference if I try to order ( I would never question anyone’s size 😉) unless I’m confused, I think that would be a really small size, like a 0 or 2. Is that right?

    • Cindy Hattersley says

      Hi Diane

      These looser styles (if you don’t want them super slouchy) require me to size down because of my waist. For reference I have a big behind and a small waist. I am 5’4 long waisted (overweight currently) and weigh 128 (hate to admit it) hope that helps!

  29. carol says

    Being pear shaped i neer quit wearing bootcut jeans When i saw wide leg jeans on line i bought 6 pairs!! skinny jeans dont work for everyone but you look great always

    • Cindy Hattersley says

      Hi Carol

      You are so smart to do that. If you find a pair you love buy several. Otherwise they change them up and you can never find them again. Great advice!

  30. Christine says

    I’m really enjoying the return of the boot cut jean and the flare Jean. I’ve got them in blue, black, and white. I agree that the skinny Jean has to be retired. I’m also not loving the mom jean, but I do love the slouchy comfort of the boyfriend jeans rolled up!

    • Cindy Hattersley says

      Hi Christine

      We had the big hair and the mom jeans. I guess if we had no memory of that we might embrace them, or maybe not??!!

    • Robyn says

      I’ve enjoyed the boot cut as well. I recently purchased a white pair of jeans I think they’re called the Billie bootcut from Madewell. I also wear the white straight leg from Jcrew. White jeans are a staple for me.

      • Cindy Hattersley says

        Hi Robyn

        I need to get in to Madewell and try some of theirs. I have always liked them but we do not have one close here. Thanks for sharing!

  31. Kathy says

    Interesting that you say you have the petite version so that they are not rolled up. However, petite also has torso adjustments for the petite figure. I am 5’4″ and typically petite length is best, but I also am long-waisted, so petite pants are way (WAY!) to tight through the crotch for me. I either hem regulars or fortunately this year have found shorter versions that are ankle pants for most but regular for me. Just wanted to warn others who may think petite only means shorter inseams.

    • Debbie Klausing says

      I’m with you on the way petites fit! I’m barely 5’4″ 123lbs. but find petite pants very uncomfortable!
      I love jeans but so many that I try on tend to buckle behind the knees. Drives me crazy! That’s why I have loved skinny jeans.

      • Cindy Hattersley says

        Hi Debbie

        I agree they usually do not fit properly, but these worked because of the style. You might give them a try.

  32. Patti says

    Great post! Can’t wait to get out of pajama bottoms! Could you please tell me what jeans Jennifer is wearing in her photo at top left? I looked on her site but didn’t see that pic. Thanks!

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