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The Absolute Best Ways to Wear Jeans Over 50 and Feel Confident

Today I am joining my pal Kim from Northern California Style for our monthly Signature Style Series. I am constantly asked about jean styling after 50, so I try to revisit this topic twice a year. As we age, our style choices may change but that doesn’t mean we have to sacrifice feeling confident in jeans.They are a wardrobe staple. Let’s discuss the absolute best ways to wear jeans over 50 and feel confident and stylish. All Jeans are not created equal. Finding a pair of jeans that we can feel comfortable in and feel stylish is not easy.

The Absolute Best Ways to Wear Jeans Over 50 and Feel Confident

LOOK FOR THE PERFECT FIT

The key to looking and feeling confident in jeans over 50 is finding the perfect fit. Opt for styles that flatter your body shape, whether it’s a classic straight-leg, slim-fit, or bootcut silhouette. Avoid overly tight (skinny jeans) or baggy jeans, as they can be unflattering and uncomfortable. Instead look for a tailored look that skims your curves without being too constricting. When shopping for jeans you need to know your body type. If you are shopping online you need to know your measurements as well.

I love my Rag and Bone utility jacket with these wide leg jeans from H&M.

Rag and Bone Olive Utility Jacket & H&M Wide Leg Jeans

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Here I am wearing the J Jill boyfriend jean.

Cindy Hattersley in White and Warren Cashmere Sweater, Jeans and Artemis Design Co shoes.

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CURVY-WHAT TO LOOK FOR

The best kind of jeans should shape you from the hip to the waist, and mid-to high-rise styles are best. Curvy jeans are for those of us who need some extra room in the hips yet often have a smaller waist.

PEAR SHAPED-WHAT TO LOOK FOR

If your body is a pear shape, you need to add length to the bottom half of your body. This visually elongates it and creates balance.Anything with a high rise, straight (think long straight line), boot cut, and flared are best.

APPLE SHAPED-WHAT TO LOOK FOR

Also sometimes known as a triangle-busty with little or no defined waist. Jeans need to balance the lower half of the body with the shoulders and bust. Boot Cut and Boyfriend are your friends.

STRAIGHT-WHAT TO LOOK FOR

The key to dressing your athletic (straight) body type is by adding dimension where there is none. High-waisted and flare are your best bets.

Remember each body shape is a little bit different and does not fit the entire mold of the particular body type. For instance, I am curvy. I have more of an hourglass figure but I do have big thighs. I have found that flares that go in at the thighs and flare out at the bottom make me look like a tank. Also, the so-called mom jean with a small waist (which I need) and a straighter leg, is also not flattering on me. The straighter leg makes me look like I am the same size from the booty down (not a good look on me). Oh and to complicate things further I have short legs and a long torso.

This quilted coat (from a few years ago but I linked a few on Poshmark) and a similar version, is a great season spanning option. I am wearing it with a super reasonable pair of H&M jeans.

Best Ways to Wear Jeans Over 50 -quilted jacket and jeans

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Best Ways to Wear Jeans Over 50

The Absolute Best Ways to Wear Jeans Over 50 and Feel Confident

EMBRACE HIGH WAISTED STYLES

High waist denim styles provide coverage and camouflage a multitude of sins (tummy control) at our age. I have a small (in comparison to the rest of my body) waist so I prefer a higher waist. There is no gaping at the waist and they feel more comfortable as long as they are not too high.

OPT FOR DARK WASHES

Dark washes can be dressed up or down and create a slimming effect. This style of jeans helps to elongate the leg and create a long and lean look.

Here I am wearing the Rachel jean from Kut from the Kloth.

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ADD A BLAZER

A blazer can take a pair of wide leg jeans, straight-leg jeans, or bootcut jeans to the next level. A blazer gives a simple pair of jeans polish and relevance. I purchased these wide leg jeans at H&M (perfect hem length) and I love them. I purchased a couple other more expensive pairs that I brought home but they are going back. I purchased this slade blazer on sale at Rag and Bone and I have worn it to death. The blouse is beautifully made from Anthro and would be pretty on its own for summer. I am wearing the outfit with block heeled ankle boots from Vivaia.

silver haired woman in rag and bone slade blazer iwth jeans

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Rag and Bone Military Jacket with Jeans red scarf and hat

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The Absolute Best Ways to Wear Jeans Over 50 and Feel Confident

ACCESSORIZE WITH CONFIDENCE

Accessories can be your best friend. They can take your jeans from ordinary to extraordinary. I know you have seen this utility vest many times before. It is a favorite. I am wearing it with Margaret Oleary’s checkerboard crew in the elbow sleeve version, you can find the long sleeved version here.

The scarf is from Sophie here. The vest is older from Banana Republic similar linked below.

Utility vest with jeans, black turtleneck hat, boots and lepard scarf

Shope the Look

This jean is the Rolla’s sailor jean. It is similar to the H&M but a “cropped” (although not on me) length.I really like the style and fit of these jeans as well. The jacket is very old Eileen Fisher but I linked several on eBay below the picture.

Red linen eileen fisher jacket, H&M jeans, scarf

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Keep Distressing to a Minimum

I do like a little distressing on my jeans at times, but most experts suggest keeping distressing to a minimum. I like this pair of Kut from the Kloth jeans because the distressing is barely there.

Distressed Jeans and gray turtleneck & scarf-The Absolute Best Ways to Wear Jeans Over 50 and Feel Confident

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The Absolute Best Ways to Wear Jeans Over 50 and Feel Confident

I am still a big fan of Kut from the Kloth a jeans. The Rachel is my very favorite. They have many styles in this cut. If you have my body type, I highly recommend this brand. Experiment with different styles and find out what works for you. If you want to try a trendier style like a super wide leg, buy an inexpensive pair. Invest in styles that last. Age should never limit your fashion choices.

Poor maintenance and care of your jeans can really make your favorite pair look unflattering. Washing your denim too often wears the fabric and the color down. Putting them in a dryer is a death sentence too. Air-drying your denim pieces will prevent them from shrinking and fading

Extended Reading:

OPRAH’S BEST JEANS FOR WOMEN

IN STYLE BEST JEANS FOR WOMEN OVER 50

AARP BEST JEANS FOR WOMEN OVER 50

Is shopping for the perfect pair of jeans difficult for you? Do you have trouble finding ones that you feel are flattering? I would love to hear about it. You might also enjoy my post 10 Ways to Casually Style White Jeans After 50. Thank you for reading The Absolute Best Ways to Wear Jeans Over 50 and Feel Confident. Now let’s pop over and visit Kim. She will be testing all of the latest trends.

NORTHERN CALIFORNIA STYLE

Reader Interactions

Comments

  1. Cindy L says

    Thank you so much for this post, Cindy! I have struggled with jeans all my life — even though I love them. Now that I am nearly 70, the challenges of finding the right pairs is even more difficult. I appreciate your tutorial and guidance here!

  2. Elizabeth@pineconesandacorns says

    Cindy, love all of your looks and style. You look beautiful in every outfit! Signature Style is one of my favorite posts with both you and Kim! Have a wonderful weekend.

  3. Robbie B says

    Thank you Cindy for the great jean references. I recently bought a pair of high waisted Levis and they look good, but seem to be alot of fabric to be “ lugging” around! Question: I have noticed silver boots on fashionable ladies lately, even Stephanie Gosk on NBC was rocking a pair! Any thoughts? Also are the Vivaia comfortable? Have you reviewed them? Thanks!

    • Cindy Hattersley says

      Hi Robbie

      I love silver boots. I have a bunion and my choices are very limited, so I have not found a pair that would work for me. The vivaias are very comfortable.

  4. Dee says

    Thank you Cindy for explaining shapes and styles. A huge help!! Love all the styles especially the J Jill boyfriend jeans. Please tell us where your awesome colorful shoes can be found. ,your backgrounds are awesome!

  5. Juliet says

    Cindy! I love your wide leg jean with blazer look. And I too appreciate a high waisted styles because of the lack of gap in the back which is so irritating. You know how to rock your denim! xo

    • Cindy Hattersley says

      Hi Juliet

      I never liked that low waisted style. I would always have to purchase them larger to fit my large behind and then the waist gaped..horrible!

  6. kim says

    Cindy, Sorry I am so slow this week. Just loved all of your post and the Rachael looks great on you. I tried it in white at Nordys and should have gotten it. The KUT jeans just seem to fit right and are comfy too. Love the Rag& Bone jacket with jeans. You look great in the distressed jean too! Love the that white blouse form Anthropologie and have it on hold. It’s so pretty.
    Always love doing this with you Cindy. Now I’ve got my jeans all sorted for the new year! xo

    • Cindy Hattersley says

      I agree Kim the Kut jeans are my favorites, but I have to say I like the wide leg from H&M!

  7. Homebeforedark says

    I will be 75 this fall and I gave up jeans in my 60s. There are other fabrics more comfortable especially in our hotter growing summers. The fabric someone mentioned might be French terry. I have some Artful Homes French terry lantern pants that are cool & comfy !

    It’s a pity you don’t looove red because it sure loves you! You look radiant in red. You would look fabulous in a red room!!!!

    My new red loafers with a cheetahs on the toes arrived yesterday. Vivaia! Fun!

  8. KatheRine says

    Hi Cindy,
    I have one question for you. Do you find the H&M high rise jeans are soft and comfortable to sit in and roomy enough in the hips?
    Thank you so much for all the research and modeling you did. You always give it your all.
    Happy 💝 Galentine’s Day, you just did what this day is all about. What a gal.

  9. Linda says

    Afternoon ….. You posted an outfit with a FEED purse ….. Could you please tell me the name of the post? I seem to have lost it and I like the outfit. ….. In fact, I like most of your outfits!

  10. Nancy Burton says

    Hi Cindy-
    I have been down a rabbit hole since reading your blog today!! Loved this article! I have purchased the Eileen Fisher jacket & a pair of the KUT from the Kloth Charlotte High-Rise Culottes in Commendatory. These purchases will be perfect!! Now if I could just find the Hannoh Wessel dress & the beautiful bright shirt you have worn the The Bennet Buttondown Shirt by Maeve. Now I must get to work! Ha

  11. Dani Vandiver says

    I have to agree that the J Jill boyfriend jeans are my favorite. I wish they would come out with white for the Summer. I always have trouble finding white jeans that aren’t too stiff or see through. The waist fits great on the J Jill jeans as I don’t like high rise because they always feel like they are choking while sitting. I’m still wearing my Laurie Felt white jeans I bought a few years ago as I can’t find a pair I like. I will check out your post on white jeans. And I took the plunge and bought one of the green utility vests you show above on Poshmark. Never usually a fan of second hand but you speak of it often so I’m giving it another try. Thanks for the great posts each week.

  12. Leslir says

    Love this post! I don’t buy much as I’ve been trying to use what I already have or buy second hand. But I think I just may try the JJill boyfriend jeans. Too bad they closed the store near me. I agree with you that mixing a fresh new fun pair of jeans and mixing them with things we already have is a great way to have a fun wardrobe! Thank you for the effort to make this post. I loved Kim’s point of view but yours is more in sync with my age and body type! Way to go!

    • Cindy Hattersley says

      Hi Lesli

      Thank you so much! Kim and I are a great team. She gives a younger fresher outlook and keeps me on my toes!!

    • Cindy Hattersley says

      Hi Leslie

      I really like those J Jill boyfriend jeans particularly in the summer. I have found a couple pairs on eBay and poshmark as well. I hope you like them!!

  13. Lori says

    I’ve no problem with your posing..ha! what a comment! I love your candid, fun, honest blog..especially this one about jeans. What size did you get on the H&M wider leg jean? I bought but boy the comments on the sizing are all over the place. They didn’t have a 6 so I ordered an 8 and will have a seamstress adjust them after I wash them as some say they shrunk up quite a bit. I am built like you and stand 5’3″..if I haven’t shrunk at 59 that is…my weight is 118 most days… I hate the jean gaping at the waist but love the boyfriend jeans. I want light weight denim so I hope the commenting on these being light weight is right. I just hope the size I bought can be adjusted easily. Some were buying 2 sizes up…oh goodness!…and we are loving Loudermilk btw..thanks!

    • Cindy Hattersley says

      Hi Lori

      I actually bought two pairs both size 6. I normally wear a 4 but my weight is on the high side currently.Loudermilk is so fun isn’t he?

  14. Lynn Anne says

    I don’t think I have found the perfect jeans until I discovered Mott & Bow. They have an amazing assortment for women and men. Mine are high waisted, fit nicely over the hip and are straight legs. Thank you again for a great article. . .ps not a fan of distressed anymore.

    • Cindy Hattersley says

      Hi Lynne Anne

      Thanks for the recommendation. Jeans can be so difficult. I am going to check them out.

  15. Joanna says

    Jeans are definitely my uniform. Unlike some, I find them comfortable and ease of dressing. I just feel more like myself in them. Perhaps, it’s from being a teenager in the late 60s, early 70s when everyone wore jeans.
    I love the high waisted jeans. I hear that mid rise is trending again andI’m not here for that.
    I love dark wash and black jeans. You can dress them up easier and I think they look classier. But then, in the warmer months, I gravitate to a lighter wash. I guess I’m fickle. .

    • Cindy Hattersley says

      Hi Joanna

      I gravitate to a lighter wash in summer as well. Lighter seems more in tune with summer!

  16. Gray says

    Such a great article. Thanks! I have never thought jeans were comfortable. It’s just always been my uniform.
    Then when leggings became popular with the long tops, I was in heaven.
    I HATED low-moderate rise jeans – muffin-top city.
    Now that high rise is back, I am much happier. I have saved them all though and have every jean iteration there is. Also I have some really pretty knit leggings from when I sold Etcetera. I am saving them – they will be cool again one day! 😉

    • Cindy Hattersley says

      Hi Gray

      I agree some jeans are not. I find in my “old age” I have gravitated to stylish jeans that are also comfortable. I think that is why I have not found many pricey jeans that I love. Some can be stiff. Oh god, those low-rise jeans were flattering on so few. You are right everything comes back.

      • Judy Christensen says

        Hi Cindy,
        I thoroughly enjoy your posts and have shared your insights with many of my friends. I always tell them is I am wearing my” Cindy Hattersley look”. Since I follow you regularly I feel like we are friends, most of your ideas I like, some I adopt, some I appreciate for others and a very few I think you miss the mark. I do have a suggestion, most of your poses are adorable but please stop turning your foot inward like you are pigeon toed! You look like you are feeling awkward or trying to distract attention from something! One last request, I love your Native American silver jewelry, especially the large pendant crosses. I have been looking for them on line with no luck, do you have any suggestions? That’ all for now, until later. Have a beautiful day.
        Judy Anderson Christensen

        • Cindy Hattersley says

          Hi Judy

          I will try to correct my posing, ha ha. I am definitely not a natural. I never intended on doing fashion on the blog, especially being a model, so bear with me. I am actually doing a post next week on native american jewelry and where to find it, so I hope you will tune in!

      • Gray says

        So I’m back again on this year’s post, with a big THANK YOU! Going to try the H&M and the Rolla – both cute. I already have boot cuts and flares and straights.
        I have been trying to figure out how to wear a wider, shorter jean and it you are so right – IT AIN’T EASY!
        I saw some from Faherty last week on a woman while I was traveling, and they were very cute. Cut off hem, somewhat wide, but not the short cropped flare, which makes me look 4′ tall. I am going to try them. She said they were magic – they are not actually denim – they are some type of terry, but you cannot tell – stay tuned……😉

  17. Nancy Brantley says

    All the outfits look good but my favorite is with jacket and scarf and the cashmere and jeans. Love wearing jeans in unexpected ways…there’s no age for wearing jeans if they have the right look!

    • Cindy Hattersley says

      Hi Nancy

      I love jeans and can’t imagine not wearing them. I am so glad you like that look. I almost pulled that one. Sometimes I get a little too creative!

  18. Téa says

    I am not “brand loyal”, and the the higher waist styles (current) are the style that work the best on my petite, curvy frame. I have a short torso, so wear a regular length…Kut From the Kloth, NYDJ, Madewell, JCrew, Old Navy, LOFT and Wit & Wisdom from Nordstroms have all worked for me. I need to purchase them to fit my hips, and sometimes have alter them at the waist to make a bit smaller. I usually do this myself, or any tailor can do it. If I need denim hemmed, I usually pay the extra for “original hem” – …

    • Cindy Hattersley says

      Hi Tea

      I am not brand loyal either. If I find one that works for my body I share. Thanks for sharing yours…so helpful to others that have the same body type

  19. Jan Finger says

    I love the chico’s leather jacket!! The whole outfit is very good looking. Love your blog. Thanks for all your work.
    Jan Finger

  20. Barb L says

    Love jeans and wear always wear them (or leggings) since covid. All the info on the various brands is so helpful. These days there isn’t consistency with sizes (or brands). I’ve also lost an inch in my height so now I have to hem (or fray since i don’t sew). Love the way you accessorize each outfit!

  21. Karen B. says

    Cindy,
    You look great in all styles, but I am a straight leg, skinny jeans person. I don’t think I can go back to flared slacks or jeans having lived through the last trend (years ago). I always like the ways you use scarves to finish the look.
    Karen B.

  22. eileen chadwick says

    I love jeans and moto pants. My feeling is go with a dark wash, no distress or crop. You always want your legs to look longer..even if they are not. Also tops in the same color as jeans gives a long lean..non stop look. I buy in a resale shop for high end brans that are lived in. Frame…..DL1961….citizens of Humanity….Gloria V..is good. too. Go longer!

  23. Lynn McClain says

    Cindy, you always look fabulous! At 79, jeans are all I wear – like low to mid-rise skinnies. I’ve been lucky – can wear any jean in any store even though I’m only 5’5″ and 115 lbs. I don’t wear flares since I didn’t like them even in the 60s. What I can’t wear are skirts and dresses – look matronly and just plain old! Jeans, white and chambray shirts, tees and blazers – my forever look.

  24. Tess Matthews says

    Hi Cindy,
    I also like the Kut jeans. Just wanted to mention they are available in San Luis Obispo
    Downtown at Pippa & Ky on Higuera.
    Thanks,
    Tess

  25. Lisa H says

    Cindy, I am always so pleased to see that you link to EBay and Poshmark! I love that you show how to shop creatively with brand name bargains, and one of a kind treasures on Etsy too.
    In 2021, I decided I wanted a new pair of off white jeans. I searched all of the options on line, and ordered well over $1000 dollars worth to try on! I only ordered from stores that had an excellent return policy. Nordstrom, J Crew, Madewell, Gap. When they all arrived, I tried them in one at a time while trying to ignore the size label, and price tag. (I ordered two sizes in each.)
    The winner was AG The Ex-Boyfriend Slim. It was, of course the most expensive…. Anyway, I now have a blue wash too, know what size I take, and can always search on EBay if I need a replacement.
    I recently helped my Daughter, who is a plus size shop for jeans. She came up with two winners. The Catherine Boyfriend from Kut From the Cloth, and a skinny style from NYDJ. Both work well for her curvy hourglass shape.

    • Martha Powell says

      I agree with resale sites! Overall I have found my best jeans at consignment and resale shops. I can try on different styles and brands. I really miss all cotton denim. I will hold on to my old Levi’s bootcuts as long as possible!

  26. Bonnie White says

    Kut from the Kluth is one of the most forgiving brand of jeans out there. Many many styles to choose from and if you investigate their inseam lengths, you even find those styles for shorter and taller women. I’m tall and wear Catherine and Diana styles. Catherine in do not cuff up. It’s a great ankle length on me, very comfy and come is casual washes (lighter) darker washes to polish with few tailored pieces. I’ve finally gotten my 34 yr old to try them and she loves them too. Nordstrom has them and in the fall I bought every color of their corduroy pant/jeans. Just a comfy as the denim, I go up a size in the cords. They have a flattering white jean in spring summer with a fabric that is not too thin and not too thick. Some white jeans highlight a not so flattering skin texture if the fabric is not just right. Not a fan! I’m so glad you shared your experience with Kut. I’m in my late 60’s and love them and feel current, polished, comfortable and styled with them.

  27. Joan says

    I prefer a jean with a waist that I don’t have to worry about exposing too much when I sit down. My biggest issue with jeans is that they fit when I put them on, but after wearing them twice they are too baggy and stretched out. I find this across all brands. Similar to the comment above re: NYDJ.

  28. Jennifer says

    Your style is just so fun! I love the way you put things together. Ditto with the skinny jeans and duster! I need that extra coverage. I wear jeans 90% of the time and expect I always will. This was fun but I always feel underdressed when I see what you’re wearing 🤣 You’re inspiring!

    • Penelope says

      You look so chic in all these looks. I am kind of an apple shape and find most jeans uncomfortable. Sometimes they slide down as the day goes on. I recommend Madewell brand for anyone with similar concerns. They seem to fit comfortably even through weight variations. They use a light material in the summer months that are particularly good. I will give some of your recommended brands a try too.

      • Cindy Hattersley says

        Hi Penelope

        I think Madewell does a great job with their jeans. I do not have a store near me anymore so I have not been checking them out. Thanks for sharing!!

  29. Joanna says

    I love jeans and wear them every day, except when going out with friends to lunch or shopping. I’m pear shape so the trending straight leg suits my frame. Being tall, I prefer the higher trending waist and hope low waisted doesn’t take over again. I prefer a dark wash, medium wash or black, never light wash. I find the light, like white, tends to make me look heavier. When I downsized and moved into my new home a neighbour noted that a women over 60 shouldn’t wear jeans. What? Apparently, her husband was of that opinion. Well here I am, almost 70 and still wearing and loving my jeans.
    You wear yours well and with style.

    • Annie says

      >>a neighbour noted that a women over 60 shouldn’t wear jeans

      hahaha

      this makes me laugh, even hours later 😉

    • Marcie says

      When I was in my 60s I thought it was time to “grow up” and stop wearing jeans. I had been wearing them since I was a kid and had to buy them in the boys department because you couldn’t find jeans made for girls. Well, at that age, it didn’t matter so much. Now in my late 70s I am living in jeans again, mostly from Talbots because they are local and make a nice variety of styles and colors.

      • Cindy Hattersley says

        Hi Marcie

        I love your comment. I think there are many that share your experience. I love my jeans. I hope I am never too old to wear them!

  30. Lelsey says

    Cindy thank you for this post. I do wear jeans, though I find it very difficult to find a pair that I really like. I live in a rural area so everyone wears jeans, but not looking as stylish as you ! I hav snot ordered jeans on line but maybe I will give it a try, as the nearest good retail city is a days drive away. I follow your blog and just love your style, you always look so good.

    • Cindy Hattersley says

      Hi Leslie

      Order them from someone who provides free returns. We don’t have department stores here either that is how I discovered Kut from the Kloth. It is so hard to find jeans that work. Last year I could not find a single pair I liked. The boyfriend from J Jill (with rolled cuffs) really works for me as well.

  31. Barb says

    Thanks for the great styling ideas! I am a long-waisted petite apple, and flattering jeans are definitely a challenge. I need a mid rise for my long waist, and those are getting harder to find. The current high-waisted styles are uncomfortable and don’t stay up, with my straight hips and flat butt. I’ve had good luck with the modern slim ankle from Talbots, although now I’m thinking I look a little better with a straight leg to balance out my heavier top. I have a pair of NYDJ bootcuts on order to try as well. I’ve also learned that taking a mirror selfie of an outfit can be very enlightening (and sometimes shocking!) I’m off to see what Jennifer is wearing. You two (and Mary Ann) are among my favorite, relatable bloggers. Thanks for all you do!

    • Cindy Hattersley says

      Hi Barb

      I am probably the only person that hasn’t tried the NYDJ jeans recently. I did take a look at them before this post. I probably need to again when I can get to a department store! We have none here. We have fabulous boutiques but no department store. Great point about the mirror selfie. Trust me, it takes a lot of pictures for me to find one that works as well. I now have a large mirror in my office that really helps. Thanks so much for sharing and the kind words. Jennifer and Mary Ann do a great job.

      • Joanna says

        Keep in mind NYDJ stretch out quite a bit. I have bought them in the past and had to go down two sizes. Try on the size that fits, then try on one size smaller knowing they will stretch.

      • Barb says

        I get my petite NYDJ jeans from Nordstrom. Free shipping and free returns. I live in a rural area with few shopping options and am forced to do a lot of online buying (and returning!)

  32. cynthia willis says

    Cindy, you hit it out of the park today! I love jeans and favor the AG brand. The AG washes are very modern and their boyfriend jeans are unparrelled. The last image with the camel colored blazer was exquisite! I appreciate you.

    • Cindy Hattersley says

      Hi Cynthia

      I almost left that pic off. I wasn’t sure if it was a little too out of the box. I do wear scarves like that often. Even if you don’t have a waist, it creates the illusion of a waist. Thank you so much for your kind words. I have heard many good things about AG. Of course I need to try them, and I don’t think they have them anywhere locally. I will keep my eyes open!!

  33. Annie says

    I gave up on finding jeans several years ago. I need a Tall inseam, which is apparently relegated to the dustbin of history. And, as an apple-shaped tall person, it becomes even harder/impossible. Needing Talls means I must order online, and even if I find a regular inseam that fits well in a store and order the exact same style in Tall, it is never the same when it arrives. A disastrous suggestion often given to apple-shaped women to try maternity styles led to a meltdown in the trying-on room and several Amazon pairs that I would need suspenders to keep up. Etc. I hate that I can’t wear jeans because I love the look.

    • Cindy Hattersley says

      Hi Annie

      You are sharing exactly what is so frustrating about jeans for women our age or any age for that matter! I would give the Kut from the Kloth a try. I was in the store yesterday and some of the styles are very long. I have the opposite problem as you (long torso short legs). Now that the frayed hems are popular I can trim them myself!

      • Annie says

        Your very kind reply to my mini-rant encouraged me to try again. Just ordered a wide variety of Kut from the Kloth jeans (open mind!) and have high hopes one might work. Thank you!

    • Karen says

      Try White House Black Market. They carry lots of jeans and other pants in tall sizes. I’m 5’8″ and depending on the style, their regular inseams are sometimes long enough without ordering the tall size.

      • Cindy Hattersley says

        Hi Karen

        Thanks for the tip! Being on the short side I have the opposite problem. Usually cropped are not on me!

  34. dianne says

    I LOVE the last outfit with the camel blazer and that fabulous scarf and that sassy hat!
    Jeans – love/hate relationship for sure. I do know when I feel fit and confident I am happy in jeans.
    A have always been a rebel and tend to wear jeans that are slouchy with a beautiful cashmere sweater.
    In any event, jeans are yto have fun in and to feel good in.
    All these photos of you inspire just that – have fun, feel good and add just the right amount of sassy

    • Cindy Hattersley says

      Hi Diane

      Good point about feeling confident in jeans. They can either look really good or really bad. I was there last year. I could not find a single pair that was flattering on me. Luckily the J Jill and Kut from the Kloth save me. As I mentioned above I almost didn’t post the pic with the hat & scarf. I wasn’t sure if it was too outside the box!

      • dianne says

        Outside the box is exactly why I love that outfit so much!!! You look stunning and happy and, no doubt, turn heads when you troll by! I haven’t tried Kut from the Kloth – if they are somewhere in Paso I might just pop up and try them on. Happy Day!

  35. Anna Bifano says

    Thank you for this Friday inspiration! I just donated six pairs of jeans – when I find a pair that fit well – I buy them! (Ugh!,) Love how you pull an outfit together – we all have these pieces – your incredible style and suggestions truly make it happen! Anna

    • Cindy Hattersley says

      Hi Anna

      That is my hope that you all can find pieces in your wardrobe that are similar and will work. It is not my m.o to just keep buying and returning things. I try to use what I have for a new look. I know some get frustrated that I don’t offer new pieces every post. I want all of you to look at what you have in new ways. You all inspire me to do that. That is why I love this community so much.

  36. Deborah Monroe says

    Hi Cindy,
    I love how you can throw together an outfit. I am so jealous. The one with the scarf, hat, and blazer is my favorite. Your fashion style is amazing.

  37. Valerie Shafer says

    I took your advice and purchased Kit from the Kloth jeans. They are a good fit for me as well. They always have several styles at Nordstrom Rack- store and online. Love your style!

  38. Elizabeth@pineconesandacorns says

    Jeans are my least favorite think to buy, the jeans that I like do not look good. I am like you, a pear with hips. If I wear pants, jeans I like them to be ankle length and a little baggy. I will have to check out a few of your suggestions.
    As always Cindy, you look beautiful, stylish and exude happiness!
    Have a wonderful weekend. Hope Summer is feeling better.

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