Let’s face it Jean shopping can be a nightmare. All Jeans are not created equal. Finding a pair of jeans that we can feel comfortable in and feel stylish is not easy. Can we be honest? Most of us probably never looked all that great in skinny’s, right? It is always hard to embrace a new trend, I know. Today I am joining my pal Jennifer fro A Well Styled Life for our monthly Style after 50 Edit for a little jean styling. Let’s take a look at some of the new styles and chat about How to Look Chic in Jeans Over 50.
When shopping for jeans you need to know your body type. If you are shopping online you need to know your measurements as well.
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.
Here I am wearing white jeans (requested by my IG readers). To be honest, I don’t wear white jeans in the winter. I know they are in. I just don’t. I thought it might be fun to put together a white jean outfit that you could wear for travel. Here I am wearing a sweater by Dylan (bought locally at Roux Collective, a Michael stars tee, my favorite cuffed jeans from J Jill, a great bag from Athleta (great for travel and walking), and super comfy Gelato sneaks purchased locally at Sole Tree. All items or similar will be linked at the bottom of the post.
In this photo, I am wearing one of my favorite pieces from Johnny Was (you can find it on eBay here), American Indian jewelry from my collection, and skinny jeans. I only wear skinny jeans with long dusters or coats now.
Currently, Kut from the Kloth are my favorite jeans. The Rachel is my favorite. This one is ripped. I know many of you don’t like that but they were on sale. They have many styles in this cut that aren’t ripped. If you have my body type, I highly recommend this brand. I buy them locally at Hayley and Co. but you can buy them online. They are linked at the bottom of the post. The scarf is from Echo and the shoes from Artemis Design Co.
Here I am wearing a long cashmere duster with (skinnies again), birdies and a horn necklace from IBU no longer available similar here but similar linked at the bottom of the post.
These jeans are also the Rachel from Kut from the Kloth. I am wearing them with simple cashmere from J Crew and Birdies. You can find the J Crew crossbody bag on eBay here.
These jeans are also Kut from the Kloth (the Meg). I did trim the hems. They are cropped but not this cropped. I am wearing them with the great blazer I have owned for years from Peruvian Connection and my combat boots.
I don’t normally wear a lot of Chicos (not for any reason) but this metallic leather jacket I love. I have linked some on ebay at the bottom of the post. These jeans are old from J Crew
These jeans are another version of the Kut from the Kloth Rachel. I am wearing them with a J Crew blazer, a lulla scarf, that you can find on Poshmark here, and vintage Helen Kaminski hat & birdies loafers. FYI Kut from the Kloth has many styles on sale on their website here. The sale styles are an extra 20% off. This is a great deal if you want to give them a try.
SHOP THE POST
You might find the articles below helpful and or humorous.
How to Wear Boyfriend Jeans for Every Occasion
People Magazine Best Jeans for Curvy Women
Jeans Guide for Pear-shaped Women
Is shopping for jeans difficult for you? Do you have trouble finding ones that you think are flattering? I would love to hear your favorites. Thank you for reading How to Look Chic in Jeans Over 50. Now let’s pop over and visit Jennifer for her ideas. I know she won’t disappoint. By the way, if you have ideas for Jennifer and I for our monthly style edits drop a comment below.
A WELL STYLED LIFE
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! 😉
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.
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
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!
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!
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!
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” – …
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
I love the chico’s leather jacket!! The whole outfit is very good looking. Love your blog. Thanks for all your work.
Jan Finger
Hi Jan
Isn’t that Chico’s jacket great? I found mine on eBay.
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!
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.
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!
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.
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
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.
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!
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.
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.
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!
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.
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!!
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.
>>a neighbour noted that a women over 60 shouldn’t wear jeans
hahaha
this makes me laugh, even hours later 😉
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.
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.
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!
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.
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.
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!)
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.
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!!
Love this post, I actually found jeans from Walmart that fit perfectly and I love them.
Hi Kathy
Way to go! Would you care to share the style? I know others might want to give them a try!
They were the Lee brand, heritage, with frayed edge.
Will try to post a pic. 😊
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.
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!
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!
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
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!
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!
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
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.
Your amazing talented with content creation. Thank you!
Hi Lynn
Thank you so very much. I work hard!!
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.
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!
So many great looks. As someone who wears them all the time…I appreciate this.
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.