The Best Ways to Look Stylish in Jeans After 60

ByCindy Hattersley Hours Posted on Hours Updated on
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Let’s face it shopping for jeans can be a love hate relationship. They’re a wardrobe staple for women of all ages, but finding the perfect pair of jeans can be a challenge, especially as we age. As women over 60, we want jeans that are comfortable, stylish, and flattering. We want to feel confident and look our best, no matter what our body shape or personal style. I am going to be 70 in about a month, and I still wear jeans all the time. There’s no reason we can’t wear jeans in our 60’s and beyond. Lets concentrate today on the current styles that are available and which ones work, which don’t, and which styles are age-friendly (don’t pay any attention to anyone that says age-appropriate I hate that term). It all depends on your body type and what you feel stylish and comfortable in. Let’s chat about The Best Ways to Look Stylish in Jeans After 60.

The Best Ways to Look Stylish in Jeans After 60

The best jeans flatter, fit comfortably, and make you feel amazing. Whether you’re after a polished look for dinner out, a pair for running errands, or something in between, there’s a style out there made just for you. The trick is finding them!

Look for Timeless Styles

We like to stay current but I would avoid trends that that won’t stand the test of time. I happen to like my jeans slightly distressed but try to steer clear of overly destroyed styles. Avoid those wide leg jeans with the big cuffs (too me they look like they need to go to the tailor). If you are on the short side (like me) they will make your legs look even shorter. I can’t imagine that style will be in for long but who knows. If you want to try something trendy, get an inexpensive pair. I have yet to find a high-quality designer pair of jeans that I am willing to spend the extra dollars on. If I find the pair, I will let you know. There is nothing wrong with investing in a great pair of jeans. Think of cost per wear.

Opt for a High or Middle Rise

Mid to high rise jeans provide a smooth flattering silhouette (translation covers the muffin top). There is nothing worse than spillage over the top! High waisted jeans look better on petites, as they elongate the legs.

Know your Body Shape

I explained this in more detail in my post The Absolute Besty Ways to Wear Jeans Over 50 and Feel Confident. You might want to check it out for more details. There are plenty of options available whether you are curvy, pear-shaped, athletic, or apple. If you love flares, wide-leg, or straight, the elusive perfect fit can be yours with a little research.

The Best Ways to Look Stylish in Jeans After 60

Add Some Polish with a Blazer

The best way to dress up a pair of jeans is to add your favorite blazer.

These Madewell vintage curvy wide leg were suggested to me by one of their sales people. She was right on with the size and fit. I am always impressed by how well Madewell does with their jeans and educating their salespeople. These jeans remind me of some I wore in the 70’s. They have a high waist and are very sturdy with no stretch. This style is also flattering if you have big thighs. I am wearing a favorite Rag and Bone blazer and denim shirt. I recently purchased the Emily boots from Gentle Souls and they are super comfortable. They actually have a slight heel.

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These jeans are from the h&m and similar to the Madewell pair. They are all cotton, fit snug through the tummy & hips with a wider leg. I purchased this military jacket from Rag and Bone on sale last year and love it. It is discontinued but I found one on eBay. A fitted jacket looks nice with a looser jean.

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This jacket is vintage Ralph Lauren (size up by the way when shopping vintage Ralph), the polka dot blouse is from Aunti Oti (no longer available but similar below)I am very fond of her block print shirts. I found the jacket on Etsy. I am wearing it with distressed Kut straight leg jeans (they also come in a dark wash) and those great suede booties from Gentle Souls.

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I am pairing my Kut ( straight-leg jeans with a high-rise waist) with a wool slade blazer from Rag and Bone (size down they run small), (there are several on eBay here, and poshmark here) a simple turtleneck, a feed bag that is discontinued but in canvas it is still available, and camo birdies (some on ebay here) also discontinued.I have linked similar below.

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The Best Ways to Look Stylish in Jeans After 60

Sweaters Always Work

Who doesn’t love a sweater with a great pair of jeans?

This great leopard sweater from Zara I paired with my Frank and Eileen jeans. These jeans are magic. They have a double closure at the waist with just enough stretch for a slimming effect. For my accessories, a beautiful reversible bag from Michino Paris (gifted), and the comfy Gentle Souls ankle boot. The fabric of these jeans have a bit of stretch for comfort, so don’t order too small. I am wearing a 26.

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Mersea sweater and jeans

Here I am wearing my Kut from the Kloth jeans and the fabulous Mersea Catalina turtleneck.

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Cos Red Cashmere Turtleneck Cindy Hattersley

I purchased this COS sweater (pricey but worth it). It’s sold out but available in camel and black. It is soft and super cozy. I am pairing it with my Frank and Eileen jeans and my Artemis slippers.

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leopard sweater and jeans

Another great sweater from COS. I should have ordered a small. I am overweight currently and I have been ordering mediums. Sometimes they work and sometimes they don’t. For an oversized sweater like this a more streamlined jean looks best.

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Cos Raggy Sweater & Jeans

This COS sweater is so much fun. It is hard to tell but it is a shaggy brown and black combo. I like to pair a looser sweater with more fitted jeans. I am pairing it with my Frank and Eileen jeans.

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The Best Ways to Look Stylish in Jeans After 60

Style Them in Unexpected Ways

Boyfriend jeans, belted scarf and long coat

I love a belted scarf under a long sweater or jacket for interest. The scarf is from BR and sold out.

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Wide Leg Jeans with Eileen Fisher tee and wrap

Add a belt to define the waist. This ensemble features a great sweater and wrap from Eileen Fisher, a leopard belt, and velvet birdies.

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Grab your cashmere throw and repurpose it. I am wearing my Quince cashmere throw with a favorite pair of Artemis Design Co slippers and a favorite hat.

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An all denim look can be slimming. Here I accessorized my shirt and jeans with kilim shoes and a bag.

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There you have it ladies! With the right jeans, you can look and feel fabulous at any age. Don’t be afraid to experiment with different styles and colors. I like a high waist (that is not overly high so that it is uncomfortable) that slims the midsection. The most important thing is to feel confident and comfortable. I hope you found this post, The Best Ways to Look Stylish in Jeans After 60 helpful if you are on the hunt for a pair of jeans. Do you have a pair of jeans that you are loving? If so please share!

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96 Comments

  1. I’m like you Pamela, I’m inspired, I love the way she wears that hat just above her glasses. That will absolutely be my new look. I was never a jeans girl, but I fell in love with the cargo pants that are jeans about 3 weeks ago. I’m very, very fortunate that at 66 years old, I weigh the same as I did in high school. So the junior section in department stores has every type of cargo pants. Didnt pay more than 20 bucks per pair either !!!. Jones new york has a really nice quality cargo jeans. They were pricey, but well worth it.

    2. I liked a few of your put together stylings. Most were too trendy for my taste. I am 84, have a cared for figure, and dress more classic/trend (my adaptation). I get compliments everywhere I go on my looks and style – even being asked if I am in a movie? It is amazing what even one item one is wearing can complete the look or turn it into a train wreck. I like clothes and admit I go for pieces that I can pair with at least 4 others in my closet if possible. Not a big spender either. Have fun with it ladies and always look your best to feel your best❣️

      1. Hi Leslie

        You sound like you know your own style and know what looks best! Classics always work. I try to put an artistic spin on the classics because that is what I love.

  2. You have such a classy look in the way you wear your jeans. I’m 55 years old, and I am starting to rethink the way I wear mine. Loving the unfinished hemline, and I have a couple of jeans I’m going to experiment with in doing that instead of hemming. You’ve given me many ideas, thank you for that.

  3. You only know 1 model to model 60? If she even is. I know your article is meant to be positive & inspiring. But, all women are NOT shaped like her.

    1. Hi Brenda

      The model is me and I will be 70 in about a month. I can only model clothes that fit my physique. It is my aim to inspire women of any size, shape or color to wear what makes them feel comfortable and stylish.If you like the looks, hopefully you can find things in your own closet that you already own that you can style similarly for your size. On Sundays I share outfits of the week. After the holidays are over, I am going to feature an extended size option as well.

  4. Oh No!!!
    I recently read skinny jeans are OUT which I purchased a few this past summer and now wide leg is in? Talk about behind the trends.
    Anyway, I did purchase one pair of wide leg and Thank You for giving examples to style them up for my 60+ self👍

    1. Hi Mila

      Don’t pay too much attention to trends, but don’t be afraid to try new styles that make you feel and look your best. I am not a fashion expert. I just enjoy fashion and hope by sharing my ideas others will be inspired as well.

        1. Hi Viv

          It’s hard to make the change sometimes, isn’t it? You should wear what makes you feel good!

  5. I’m 68 and love to wear the super baggy jeans currently on trend with a pair of patent loafers. The next day Levi 501s, these remind of my youth when I wore them then.
    You are as young as you feel.

    1. Hi Christine

      I am on the hunt for a pair. I am going to check our your levi suggestion!!

  6. Our grandmothers never looked this great! Jeans look good on just about everyone and I love how dusters, denim jackets, belts, cute loafers or boots, a little bling and the right bag can make us look 40 all over again.

  7. There are several different body types! I am.the to heavier, full waistline type and have slimmer legs and look good in narrow leg jeans. The problem I have is that you basically have put a jacket with everything. This will not work on a hot day! If the jeans flatter your body type, then you can use an ironed tee, or sweater or blouse- ANY top which looks good on you! FOR my buxom, slim leg figure, I like narrow jeans and a somewhat loose top of any type correct for the weather.

    1. Tunics works well for those of us who want to wear longer tops. In summer, linen tunics or swing type tunics.

  8. I loved all the styles and ideas for wearing jeans. Hope to never retire denim from my wardrobe always been a staple. I am 76 years old NYDJ Marylin is my go to now. I have always accepted my body changes as I have aged.

    2. I love all the outfits shown here, but I live in SW Florida! I would roast in the blazers. I miss the fall weather and the autumn color clothes. It’s hard to find a stylish way to do fall in 80 degree weather! Maybe this could be the next challenge for clothing stylists! Nancy.

  9. I live in the Sacramento area and would melt in most of these looks – even in January. Any non- sweltering looks that work with jeans? RK

    1. Hi Rach

      Wow my kids both went to Davis and found their winter climate to be similar to ours here. The problem is it starts out cold, warms by midday and by the end of the day it is cold again!!

  10. I’m 72 and West jeans ask the time. I like Rag & Bone and still wear True Religion which for so well I can buy them without even trying them on.

  11. Thank-you for this refreshingly honest, real and lovely article that clearly addresses an article of clothing that is truly important for today. I, as well, wear jeans as an almost uniform and pair them with blazers (Theory, Max Mara, J Crew) and cashmere sweaters, crew neck with my favorite being turtleneck. Seasonally, sandals, loafers and boots (my favorite look!) I am 74 years, slender and 5’4 “ in height. I wear high-rise as well as mid-rise and have found Madewell to be good fitting and the place I always gravitate. However, I recently had a pleasant surprise at J Crew in finding Slim Wide Leg jeans (full length) that are gloriously non-stretch and fit perfectly! Victory! Thank-you again for your entry and I have enjoyed the review comments from ‘women who wear jeans’!

    1. Hi Yvonne

      Thanks for the J Crew recommendation. I wore their jeans for years and found they weren’t fitting me properly the last few. I am going to take a look the slim wide leg.

    1. Hi Mary

      Are you speaking of the simple black one, or the green and black? The black is form Rag and Bone (old from eBay) I linked one. The black and olive green is from Feed (my favorite bag). They no longer make the leather version.

  13. I wear high waisted straight denim jeans by Ralph Lauren. They are ankle length. I wear these with blazers by Ralph Lauren or Brooks Brothers.

    1. Hi Shearie

      I have never tried Ralph’s. What style do you like? I am a huge Ralph fan.

  14. I’ve bought two pairs so far of Sidefeel Womens Jeans Trendy 2024…on Amazon. I anticipate living in these all winter.

  15. Finally! I’m 72, size 4, 5’5″ and I love high waisted jeans with a little flare and a bit of stretch. I’ve bought two pairs so far of Sidefeel Womens Jeans Trendy 2024…on Amazon. I anticipate living in these all winter.

    1. Not a fan of short length Jean’s at all. They are freezing and unflattering. Fit is key and a style you love, yes you can rock any style you love.!

  16. The last time I looked good in jeans was in 1990 and they were Trussardi. These days, I weigh more and of course it settles on my thighs, so jeans have become my nemesis. Did splurge on some Max Mara jeans in Rome last year, but only because I had lost 3kgs (from gastro that week) of course I put the weight back on and couldn’t zip the wretched things up – so they went off to the charity shop. I envy women who look good in jeans, but prefer skirts these days

    1. OMG I agree with you and I too wear skirts . I love the wide leg jeans and wear those when I need to put on a pair. Skirts and boots are more my style because I have more freedom and movement. I am in my 60’s and no longer want my jeans or pants to to fit tight. Hats off to those who can still wear 👖.You Go Girl!!🙂

    2. Susan, you reminded me of my beloved Trussardi jeans. They fitted me so well and don’t believe I have ever found any that come close to them. Of course I was much slimmer then.

  17. Gosh, love your looks here. And we’re similar ages, I’ll be 71 this month! I have to hunt high and low for decent fitting jeans for my pear shaped figure. Finally, finally Democracy jeans seem to be the ticket. No gap in the waist band ( they have that hidden elastic sewn in) and a light bit of stretch. And come in a few washes and style types. And they have lasted for a few years, though when I see a color I’d like, I have got another pair. Keep showing us your great style. You’re inspiring me to try and look great!

    1. First time ever that I looked at an article showing me what to wear that I actually thought” I can do that!.” Love your combinations and different style jeans. We are same age and body type so finally I see myself. Thank you, I am inspired!

    2. Like you I have found democracy jeans to be the best fit for me. I am also in my seventies and I’m slim so I really can wear any jeans but democracy are so comfortable. Whenever I find them at Marshalls or TJ’s I grab them.

    3. Hi Kathleen

      Ugh! the gap in the waistband. That is why I never liked the ones that rested on the hip!!

  18. I’m not a fan of high rise jeans, ostensibly because they end up under my boobs and because I love belts, the high rise cuts me through the abdomen and emphasise the slightest potty tummy. Thus I settle for mid-rise which generally end at my natural waist anyway, so win-win. But trying to find mid-rise jeans at the moment is hard. Until last week when my dog was ill and I went online shopping to boost my mood. I found two mid-rise, mid-blue jeans, straight leg but slightly narrower for $A99 for the two. They’ve arrived and fit perfectly but I’m having them shortened. Very happy.
    Must tell you, one day I wore a denim shirt, denim jeans, leopard skin belt and some Vivaia’s and two cheeky young chaps outside the supermarket said, ‘Love how you’re rocking the double denim!’ Still trying to work out if they were mocking or not but would prefer to think it a compliment at 73.

    1. I think the young chaps were being honest. The know their fashion. I also need a mid rise jean. Can you share the brand or store? Tx.

  19. Cindy I was at a major department store about 15 years ago and carrying a pile of jeans..must have looked discouraged. Another customer asked if I had tried Diane Gilman and I wrote that down. Now her petite jeans are my only jean brand since then. I prefer slim leg ones and straight leg styles and have white, midwest and black. As I am 5 foot tall I still have to have them shortened but am happy. These last forever and I can style them all year round. Today I did see a site that showed beige jeans so this could work all year also depending on the other parts of the outfit. Older women can wear jeans! it’s all in how you do it in my opinion. My ‘house’ and garden’ jeans are whatever pair is on its last moments. Overall I. like the look with loafers for colder months plus low heeled boots or ballet flats for warmer days…also sandals in the summer. The one style of jeans I won’t wear are torn or ragged ones..never low waist. I am 81. thank you, Cindy for your research and commentary.

    1. Hi , I’m Gayle and love your looks im 5 ft 9 in tall just turned 80 years old my idea is you like something you wear it do your own thing love my jeans and love hats but being tall mabe I shouldn’t wear them not a perfect 80 body but if I’m comfortable and feel good with something I’m happy keep up good work look great .🙏🏼

    2. I agree, no ragged washed out look! I’m 89, 5ft tall and weigh 107. I wear jeans every day. I look for dark wash, straight leg and mid waist. Price is a problem, I will not pay $65.00 and up for my jeans! I modestly say I look about 70 yrs. old.

  20. Quince offers a stand-collar blazer (both in ponte and Italian wool) very similar to the Slade.

    Thanks for the many stylish ideas! I’ve had the best luck, honestly, with Old Navy jeans. I recently made a concerted effort to find a pair of pricey jeans that lived up to the hype, but I walked out of Nordstrom with an $80 pair of Wit and Wisdom. It really comes down to personal preference and comfort. And of course body type.

  21. I read many years ago that when trying on jeans take in 3 pair of the same size and style due to the cutting and sewing discrepancies. Yesterday I did just that at Old Navy. Their OG loose high waist have nice pockets in the back that don’t minimize my already small booty. Each pair did fit “a little differently “ BTW I’m short 5’4” and I tried on the petite, perfect length but too short in the rise…I’ll need to hem or cut off for a frayed edge. All in I’m happy with a pair or $25 casual jeans !!

  22. I am coming to terms with some weight gain in the past five years. I’ve had some life changes. I’m healthy though, and my doctor confirms. So jeans have been a much thought about subject, since I’ve had to replaced my collection!
    I am 5’7”. 164lb…there I’ve said it! Coming from years of wearing a size 8-10 to now size 12-14. I have a short waist and an hourglass shape.
    My very best fitting and feeling jeans are the AG Ex Boyfriend. They fit very much like Levi’s 501, and come in lots of washes. I have both 31 and 32. Both blue and off white.
    I also bought a pair on eBay, and cut them off for Bermuda length shorts, following instructions from a YouTube video. Turned out perfectly! Wore them all summer.
    My bargain recommendation for people with an hourglass shape is Gap jeans. That brand seems to always fit me well. My biggest issue with many jeans is a gappy waist. I bought some really cute wide leg jeans there recently!

    1. American Eagle stove pipe jeans fit my hour glass shape with the high waist making my legs looks lengthy(slim). Very comfortable and stylish.

  24. Great minds!!! Funny I did a YouTube video and said all you need it a white t-shirt and a pair of jean. Then go look into the depths of your closet and look for some vintage top to go with it. Funnily enough I needed jeans quickly and simply went to Chicos. Found some great jeans with easy waists that are actually comfortable.My tops all came from the depths of my closet. But now I’m on the hunt for wonderful white t-shirts. It should be easy, right? Nope but I’m getting there. I’m so impressed the way you shop on ebay. I shop there also but mainly costume jewelry. I’m going to try some of your links. You’re a pro at auction shopping. You always look fabulous. So much style!!

    1. I wear jeans nonstop. I love that denim came from Nimes, France to be called de Nimes. I look best in jeans, being long legged and apple shaped. What I do not get is the ragged edged ankles which could be improved it seems to me with low boots or even high top sneakers.

      1. Hi Sarah

        I love the raw hem as long as it isn’t too ragged. My legs are short (long torso) so most jeans are too long for me!

  26. You completely nailed this Cindy. I especially love the suggestion of a blazer. Sweaters are greater but can make one invisible. Im enjoying cooler weather to try out my new jeans. And I was very impressed with the service at Madewell. Hard to find a good pair of black jeans but found the perfect pair there.

  27. Love all the looks! My fave takeaway is the Alice Frindge sweater coat with belted scarf underneath! LOVE!
    You always look cute.

  28. I have multiple pairs of J Jill jeans. I bought the first ones in 2005. They were the original Tried and True staight jean. They have a wider leg all the way down. J Jill discontinued them and came out with a slim fit that doesn’t fit my knees! (!large bones in legs). Now I can’t find any jeans that fit. I wear petite size 2 but need the width and stretch for comfort.

      1. Perfect jean. I have a closet full of them. Wish the rise was lower again. I don’t like high rise at all.

        1. Hi Joleen

          I think the rise all depends on the body type. I like a mid rise best. I have a smallish waist (large butt) and the low slung ones always gap at the waist on me.

      2. I agree 100%. The waist and legs of NYDJ Marilyn jeans are proportioned and comfortable. Best I have found for my size: 5’9”” 170 lbs. and appropriate for my age of over 70 yrs.

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