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28 Best Jeans for Women Over 50 That Are Stylish and Comfortable

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There’s no denying that a good pair of jeans is essential to any wardrobe. Finding a pair that are stylish, comfortable, and fit well, however, can be a tall order — especially as we get older. Thanks to changes in our body shape that come with age, sussing out the best jeans for women over 50 can be a bit like finding a needle in a haystack. But fear not, friends — we’ve found plenty of pairs of denim that will not only fit you perfectly, they’ll be versatile enough to wear with everything from sweaters and fall boots to tees and tanks. Read on for our best tips on how — and where — to find the best jeans for older women!

Deals on the Best Jeans for Women Over 50

What are the best jeans for women over 50?

What type of jeans should an older woman wear?

First things first: What type of denim is right for you? From trendy styles, like boyfriend jeans and distressed denim, to classic boot cuts or straight legs, the choices can seem daunting. 

The good news is that outdated rules about choosing the best jeans for women over 50 solely based on your body type are long gone. Shorter women look just as good in bootcut denim as they do in slimmer cuts, and anyone can rock a pair of gray or even velvet (!) jeans.

Ultimately, the best jeans for you are the ones you feel the most comfortable and confident in. They won’t ride up or slide down, bunch up at the bottoms, or restrict you. They’ll feel like a second skin (almost as cozy as your go-to pair of leggings), and they’ll look great whether they’re dressed up with a blazer and heels, or down with your favorite tee and sneakers.

Can a woman over 50 wear skinny jeans?

The answer to this question is a resounding “Yes!” Skinny jeans aren’t reserved for any particular age group, or body type, for that matter. In fact, the term “skinny jeans” is a bit misleading, as it’s not referring to the type of body the jeans are for, but rather the body-hugging fit of the jean. If you’re looking for the best jeans for women over 50 that’ll give you a sleeker look, a pair of skinny jeans in black, or a dark wash like an indigo, are hard to beat. In reality, the only “rule” we have when it comes to wearing jeans is to choose a pair that feels great on you.

Speaking of comfort, most women find that mid-rise or high-rise styles work best — particularly when it comes to preventing any unwanted exposure when you sit. Low-rise jeans can also lead to that uncomfortable “muffin top” feeling we all do our best to avoid, in which the sides of our waist begin to spill over the sides of our jeans. (No thank you!)

Sizing jeans: finding your perfect fit

Finding the right fit may require taking a few specific measurements, such as your inseam (aka the distance from the inside crotch seam to the bottom of the leg), your waist (which should be taken slightly above your belly button), your hips at their widest point, and the circumference of your thigh. 

When it comes to size, however, even the best jeans for women over 50 may vary greatly by retailer, so if you’re ordering online and are unsure of your size, it might be helpful to check the reviews to determine if the specific pair you’re eyeing fit more true to size or if they run small or large. Reviews can also tell you if they tend to stretch out over time or get overly baggy. In-person, you can avoid fitting room frustration by bringing multiple sizes into the dressing room, which will reduce the amount of time you spend searching for your best fit. 

Once you’ve found the best pair of jeans for women over 50 that feel great on you, having an extra pair that are a size larger than your normal size on hand is never a bad idea, either — especially on days when you’re feeling bloated or simply plan to enjoy a big meal. Always remember, the clothes should fit you, you don’t have to fit the clothes! 

Best way to wash denim jeans

It might seem like a no-brainer, but when it comes to how to wash your jeans, there are a few things to keep in mind. First, you’ll want to wash your jeans inside out separately before your first wear, as some dyes tend to bleed onto other clothing items. After that, you might want to continue washing them inside out in order to best preserve their color: The more you wash them, the faster the color can fade, so sometimes less is more!

As for how often you wash them, it’s really a matter of personal preference. Some women prefer to launder after each wear, while others wash them only when they become stained or start to smell. Others still opt to hand wash their jeans by soaking them in water for 15 to 30 minutes and rinsing well. 

Tumble-drying your denim is where things get tricky. Not only can high heat fade your denim, it might lead to shrinkage over time, so line-drying your denim isn’t a bad idea — even if it means your favorite pairs are out of commission for a day or two. 

Shop the Best Jeans for Women Over 50

J. Crew 9″ High-Rise Toothpick Jean

Best distressed jeans for women over 50
Great deal!

Buy from J. Crew, starting at $65

Why we like them:

  • Available in classic, petite, and tall sizes
  • Very light distressing
  • Made with premium Italian denim

The right amount of distressing can give a pair of the best jeans for women over 50 a cool, carefree vibe, and a little really does go a long way. Too many rips and holes, and the next thing you know, you’re in shipwreck territory! That’s why we love these tastefully-distressed jeans in the Charcoal Wash shade from J. Crew, which have minimal detailing that proves less is more. Like many of J. Crew’s jeans, they’re available in a wide range of sizes, including classic, petite, and tall lengths, and have a relaxed, cozy look. They have flattering Perfecting Pockets™ too!

One reviewer raved, “I’ve been looking for dark grey jeans for a long time, and I am thrilled to have found these! The wash is not too distressed and it looks better on me than lighter grey jeans. The fit is really good for me, and for some reason J. Crew and J Crew factory jeans fit better than most of the $$$ designer jeans I have tried in the last few years.”

Spanx Flare Jeans

Best sailor jeans for women over 50
Best Jeans For Women Over 50

Buy from Spanx, $148

Why we like it:

  • Beautiful indigo wash
  • Hidden core-shaping technology
  • Goes up to size 3X

Sailor jeans is a denim trend we’re loving, and these may be one of our favorite pairs. The Spanx Flare Jeans feature a slimming high-waist, and have shaping in the mid-section to smooth any tummy bulging. This makes for a very comfortable and flattering fit, sort of like the best shapewear leggings, but with the cool factor only denim can give. The pull-on style is great — why fiddle with a button and zipper if you don’t have to? The back pockets are high (gives the illusion of a tighter tush) and have deep pockets — perfect for your phone or to stash a debit card. Available in tall, petite, regular, and going up to six 3x, we think every lady needs to own these. Regardless if worn with a blouse, bodysuit, sweater or blazer, this modern take on the retro-style is going to turn heads.

Here’s what one happy customer had to say: “I love these jeans. I am 5-foot-7, and I’ve been ordering the regular length but need to wear heels with them. This time I ordered petite, so I can wear flats. It works. The jeans are extremely comfortable and stay in place unlike other brands that I have to pull up all day. I highly recommend them.”

Amazon Essentials Women’s High-Rise Skinny Jean

Best Amazon Essentials jeans for women
Best Jeans For Women Over 50

Buy from Amazon, starting at $20

Why we like it:

  • Available in four different washes
  • 3,000 5 star ratings!
  • 79 percent cotton

Jeans can be pricey but not these! Amazon Essentials are definitely worth checking out if you’re on a budget. They have great reviews, mainly praising them for their stretch and fit. They are made of mostly cotton but have a bit of spandex to smooth over curves just right. The skinnies hit right at the ankle, making them perfect for booties, heels, or flip flops (while the warm weather is still with us). Wear to work, a casual date, or when loafing around the house. They’ll make you feel amazing!

One happy customer had this to say: “These jeans are as good as jeans I’ve paid a lot more for. Quality is exceptional. I would definitely buy again.”

Gloria Vanderbilt Amanda Classic Madison Jeans

Best slim fit jeans for women over 50
Best Jeans For Women Over 50
52% off!

Buy from QVC, $48

Why we like it:

  • Goes up to 24W
  • High-rise
  • Lifted back pockets

We all need that pair of jeans that can be turned to no matter how we’re feeling style-wise. These Gloria Vanderbilt Amanda Classic Madison’s may be them. They’re high-waisted, which creates a streamlined look, and the contour material brings extra shape to the leg without making one feeling stuffed in. Made from a blend of cotton, polyester and spandex, these dark denim beauties look great with a variety of footwear, including one of the best boots for fall, heels or lightweight running shoes.

GRAPENT Womens Flare Jeans

Best Jeans for Women Over 50

Buy from Amazon, $23

Why we like it:

  • Available in 12 different colors
  • Fun y2k style
  • Good for short and/or pear shaped

What’s great about these y2k style jeans is that they’re not too baggy, so they can still be worn to meetings and semi-dressy events. They’re high-waisted, slimming the mid-section, and then opening like classic wide-legs beyond the thigh. They come in a variety of lovely colors, including brown, green, and white, plus look very sophisticated when paired with a tailored blazer. According to some happy customers on Amazon, they’re great if you’re on the petite side or have a small waist and fuller hips. Hitting right at the ankle, they shouldn’t drag on the street, and they have some stretch too!

Promising review: “I decided to give these jeans a try after reading the reviews and must say, I am positively surprised. I am short 5-feet-2 and 125 pounds with narrower hips but a lot of butt and big thighs. Usually, jeans will be loose on my waist and tight in the thighs. I ordered size S and think the chart is [accurate]. The jeans fit like a 4-6. They are roomy in all the right places, and most of all, perfect for shorter women like me. In fact, I am considering ordering them a size smaller, since they are roomier than expected. If you are living in a size 0 or 2, I’d recommend ordering an XS.”

NYDJ Marilyn Straight Jeans

Best stretch jeans for women over 50
Best Jeans For Women Over 50

Buy from QVC, $99

Why we like them:

  • Available in a variety of washes
  • Regular, plus, and petite sizing
  • Made with Sure Stretch denim technology so they keep their shape

Commerce editor Elizabeth has these Marilyn NYDJ jeans, and says they’re some of her go-tos all fall and winter long. “I’ve always struggled to find jeans that fit my small waist, big booty, and thick thighs. Straight-leg jeans used to be an automatic ‘no’ for me, but these are amazing. I love the classic fit, and how they hug my curves without feeling tight. Plus, the rise is high enough, even on my long waist, that I don’t get the dreaded ‘muffin top’.” A hint of stretch makes them feel super comfy, and helps them keep their shape season after season. Some of the more popular washes sell out fast, but with six stylish shades available, you’ll be able to find one in your size. Another tip from Elizabeth? “I have these in two sizes, so I can still wear a pair on the days I’m feeling a little heavier or more bloated. I highly recommend making room in your closet for this technique!”

Good American Good Legs Flare Never Fade Jeans

Best bestselling jeans for women over 50

Buy from Good American, $139

Why we like it:

  • No waist gapping!
  • Flat-tummy tech
  • Made with recycled materials

Flares are back in style and we’re so glad. The flattering cut works great on everyone, and looks exceptional with a pair of heels. Our current favorite pair? The Good Legs Flare Never Fade Jean from Good American. They have a high-waist (also universally flattering), and super stretchy fabric that can fit up to four sizes. The waistband is gap-proof and includes tummy smoothing technology, so you feel tight without feeling tight — if you catch our drift. Good American is a size-inclusive brand, so no matter if you’re a 00 or 30, you’ll find something that makes you feel incredible. We also love that they’re dedicated to reducing their carbon footprint and use eco-friendly washes and recycled materials in their clothing.

J Brand Darted High-Rise Flared Trouser Jeans

Best dark denim jeans for women over 50
Best Jeans for Women Over 50
70% off!

Buy from The Outnet, $75

Why we like them:

  • Stretch denim
  • Slimming
  • Dark wash

If you’ve always wanted to look like a Charlie’s Angel, here’s your chance. We’re obsessed with these dark denim trousers for their vintage look and flattering fit. The high-waisted jeans flare at the bottom, elongating the legs, and the material is stretchy. The fits tailored enough to work for the office, but also stylish enough for night’s on the town. I’d pair with a cropped sweater, but these jeans would also look great with a blouse and blazer, or simple tee. Switch up the vibe of the outfit by selecting different style of shoes, and don’t forget to curl your hair like Farrah. If you’re petite you may need to have them taken in, but if your statuesque you may have just found your perfect pair.

Levi’s Women’s 311 Shaping Skinny Jeans

Best Levi's shaping jeans for women
Best Jeans For Women Over 50
30% off!

Buy from Amazon, starting at $21

Why we like it:

  • Variety of different washes
  • Light
  • A little spandex

If you love the look of skinny jeans but dislike the thick spandex some contain, you’ll dig these. They’re ultra lightweight, and conform to your body’s curves. That being said, they don’t have a lot of stretch, so you may want to size up a bit if wiggle room is important to you. They come in lots of different washes, sit at the waist, and look amazing with booties or heels. They’re available in plus size, as well as standard. When washing, it’s recommended that a liquid detergent is used instead of powder.

One Amazon customer said she had a “tough time finding jeans” because of her petite but athletic build. For her, the shaping skinny jeans have been “a lifesaver,” and she loves how “feminine” she looks in them.

River Island Blue High Waisted Wide Leg Jeans

Best split leg jeans for women over 50
Best Jeans for Women Over 50
River Island

Buy from River Island, $71

Why we like them:

  • Relaxed fit
  • Small side slit
  • Soft

Baggy jeans are one of the biggest denim trends for 2023, and the good news is you don’t have to go too baggy to take part. Take these jeans, for example. They sit high on the waist but skim your hips and legs, similar to your favorite pair of work slacks. In fact, they even have a small slit at the bottom, so your cute heels can peep through. They don’t have stretch, but you don’t need it with jeans like this. They’re relaxed enough to make you look casual cool, but still fitted enough to stay clear of looking sloppy — that’s never stylish.

NYDJ Women’s Marilyn Straight Leg Velvet Jeans

Best velvet jeans for women over 50
Best Jeans For Women Over 50

Buy from Amazon, starting at $77

Why we like them:

  • Can be dressed up or down
  • Soft, comfortable material
  • Cotton-blend fabric has a bit of stretch

If you’re looking for a dressy pant that’s as comfortable as your favorite denim pair, this high-rise velvet skinny jean from NYDJ is a great bet. The high-rise waist has an elongating effect, while the cotton-blend black velvet offers a bit of comfy stretch. Dress them up with heels or down with a classic white tee — they might just become your new go-to pair of pants!

7 For All Mankind Alexa High Waist Crop Wide Leg Jeans

Best cropped jeans for women over 50

Buy from Zappos, $198

Why we like them:

  • Can be worn with practically any shoe
  • Slightly flared hems
  • Cotton-blend material includes spandex for a bit of stretch

Cropped jeans are a must-have in warmer climates, and 7 For All Mankind has crafted the perfect pair. The wide-leg style is comfortable and chic, rather than baggy, and the slightly flared hems and broken-in denim give off a somewhat vintage feel. These jeans are the perfect pants to pair with sandals or tennis shoes, but would look equally cute with a great pair of boots come fall.

At first, one skeptical shopper “wasn’t so sure how these would look and fit on my middle-aged thicker thighs,” but was surprised to find that “they’re very comfortable” and “look cute with just about any shoe or boot.” She also called them “forgiving,” and says she wants them in more colors now!

NYDJ Alina Pull-On Skinny Ankle Jeans

Best pull-On Jeans for women over 50

Buy from Amazon, starting at $61

Why we like it:

  • Lift Tuck technology
  • Super stretchy
  • Button and zipper free

There’s no “sucking it in” when owning a pair of the Alina Pull-On Jeans from NYDJ. They’re comfy like leggings but far more chic. They hug curves and slim without making you feel suffocated. Their magical contouring abilities comes from their Lift Tuck technology that smooths your front while raising your bum. You’ll love them so much, you’ll want to wear them every day!

Promising review: “Love, love, love these jeans. Quality denim and amazing fit. Long enough, too, as I’m 5ft 9in tall. Might buy another pair in another colour…”

Lee Relaxed Fit Tapered Jean

Best tapered jeans for women over 50
Best Jeans For Women Over 50

Buy from Amazon, starting at $31

Why we like it:

  • Side elastic waistband
  • 99 percent cotton
  • Classic look

Do you pray to the denim gods to kill the skinny jean trend? They may have heard you. The Lee Tapered Jeans slightly remind us of the jeans of the 80s and are a far cry from the leg-clinging denim that’s been circulating. They’re relaxed but not baggy, becoming more tailored toward the ankle for a more mature look. They’re very comfortable, work wonderfully for daily wear, and can be paired with boots, heels, or your favorite sneakers. More than 2,000 people on Amazon love them for their comfiness.

Good Legs High Rise Skinny Jeans

Best Good American jeans for women over 50
Best jeans for women over 50

Buy from Good American, $139

Why we like it:

  • Slimming
  • Breathable
  • No gapping

Remember when we all rediscovered how comfortable (and flattering) leggings were? Well, these jeans from Good American are the next best thing. The stretchy cotton blend keeps you from getting sweaty, even though these things hug every gorgeous curve. Bumps, lumps, and jiggly bits are smoothed away by the slimming design. Contouring in the waist keeps you free of gapping. These jeans are classic enough to wear every day, but also work for date night. Also available at Nordstrom.

Levi’s 721 High Rise Skinny Jeans

Best high-waisted jeans for women over 50
best jeans for women over 50

Buy from Levi’s, $70

Why we like them:

  • Made with super-soft stretch denim
  • Classic blue wash
  • Keep their shape

Levi’s is one of the most beloved denim brands for a reason — their jeans are the perfect blend of comfort and style! This high-waisted pair is no exception, thanks to the timelessness of the classic blue wash, which complements the modern, leg-lengthening silhouette. Best of all, these jeans will keep you comfortable all day, thanks to the super-soft stretch denim that actually keeps its shape with continued wear! These are hand-wash only, but we think it’s well worth it for a pair that could very well become your new favorite pants.

One happy reviewer wrote, “Love these jeans!” and called this pair her “new favorite go-to.” Keep in mind that reviews said these jeans run small, so you might want to size up.

J. Crew 8″ Toothpick Jean

Best white jeans for women over 50
best jeans for women over 50
J. Crew

Buy from J. Crew, $90

Why we like them:

  • Available in classic, petite, and tall sizes
  • Stretchy cotton-blend fabric
  • Cropped length

It’s hard to imagine an article of clothing more clean and crisp than a white pant, and while they might not be for everyone, we’d be remiss not to include a great pair of white jeans on our list of the best jeans for women over 50. This skinny pair from J. Crew is made with a special cotton-blend fabric that keeps its elasticity, so it stays stretchy enough to keep you comfortable without sagging over time. The cropped length makes these jeans perfect for cool spring and summer days, and they come in a range of lengths to suit classic, petite, and tall sizes. We can probably all agree that the whole “no white after Labor Day” adage is outdated, and it’s a good thing, because these pants would also look super cute with some ankle boots in the fall!

One relieved J. Crew shopper called these her “white jean soulmate,” saying she could “happily rock these year-round, but for summertime — perfection.” She appreciates that they’re not “too gape-y at the waist, or too stretchy, baggy, and saggy once you wear them for a few hours,” and that “they hug my waist and hips in a flattering way” and “aren’t see-through, bless ’em.”

Lee Women’s Flex Motion Straight Leg Jean

Best affordable jeans for women over 50
10% off!

Buy from Amazon, $29

Why we like them:

  • Nine washes to choose from
  • Elastic waistband technology
  • 69% cotton

Remember Lee jeans from when you were younger? Well, they’re back and better than ever. The budget-friendly brand makes jeans in a range of stylish cuts and washes, and we’re fans of this straight leg design. Comfortable, versatile, and available in basically any shade of blue (or black!), these jeans will likely become an everyday go-to right away!

J. Crew Curvy Toothpick Jean

Best dark wash jeans for women over 50
best jeans for women over 50
J. Crew

Buy from J. Crew, $45

Why we like them:

  • Available in sizes 23-37
  • Come in classic, petite, and tall lengths
  • Sleek indigo wash

The right pair of dark jeans can effortlessly take you from day to night, making them a true staple for every wardrobe. These toothpick jeans from J. Crew are even more special, thanks to their curve-friendly design, which features a narrower waist to avoid that oh-so-annoying gap that those of us with fuller hips and thighs are all too familiar with. That said, there’s also ample room for your legs and butt, making these jeans a rare breed. As if that weren’t enough, they’re made with J. Crew’s stretchiest denim for all-day comfort, and are available in classic, petite, and tall lengths in sizes 23-37. What’s not to love?

One fan of these jeans, who is “short and very pear-shaped,” said she often has trouble finding jeans that fit well, but that “these are the ones that are truly made for people like us.” She appreciates that “the quality is excellent in that there’s stretch, but the jean doesn’t look and feel like a cheap jegging,” and that “the jeans are naturally ankle-length, so regardless of the size you wear, they aren’t too long at the bottom.” She even said she ended up buying all three pairs she tried on!

Lee Relaxed Fit Straight Leg Jean

Best colorful jeans for women over 50
Best Jeans For Women Over 50

Buy from Amazon, $39

Why we like them:

  • More than 17,400 reviews on Amazon
  • Come in more than a dozen colors
  • Comfortable

If the term “colorful jeans” conjures up thoughts of bubblegum pink pants, let this pretty pair by Lee assure you that there is, in fact, a happy medium! These super comfortable relaxed jeans come in a variety of bright colors that will liven up your closet. Falling a little below the natural waist, they’re a stylish alternative to high-rise, and still offer clean, slimming lines. More than 10,000 folks on Amazon love them enough to give five-stars.

Promising review:I’m in my fifties and these are really working well. I have full thighs, behind and a belly. These are hugging me in a flattering way, without being tight at all.”

J. Crew Curvy Vintage Slim Straight Jean

Best plus-size jeans for women over 50
best jeans for women over 50
J. Crew
22% off!

Buy from J. Crew, $65

Why we like them:

  • Inclusive sizing options
  • Stylish high waist
  • Medium wash fabric

Every woman needs a good straight-leg jean in her wardrobe, and this curve-hugging pair from J. Crew are as comfy as they are classic. Inclusive sizing options — including regular, petite, and tall lengths in sizes up to 35 — make these jeans best-sellers, and we’re huge fans of the chic high waist and medium wash fabric, which you can easily dress up or down. We love the way these look styled with a breezy button-down, as pictured, but these would be equally as cute paired with a cute tee in the summer or chunky knit sweaters come fall.

One J. Crew customer purchased these in a size 32 and said, “I have never once put a pair of jeans on my body and liked everything about them the first time I put them on. Never. UNTIL I bought these.” She went on to say, “the cut of these jeans is so flattering,” and “a little stretch helps to make them fit oh so comfortably.” She even added, “I feel like I’ve found a denim unicorn!”

Rag & Bone Dre Slim Ankle Boyfriend Jeans

Best boyfriend jeans for women over 50
best clothing stores

Buy from Neiman Marcus, $225

Why we like them:

  • Chic medium-light wash
  • Slightly loose fit
  • Ankle-cut

In addition to boasting a cheeky name, boyfriend jeans are insanely comfy for all body types and look perfect whether you’re enjoying a casual lunch out or running errands on a weekend afternoon. With their hallmark loose fit and ankle crop (which also looks great rolled up), it’s no surprise that this jean style — a favorite of 50-year-old Jennifer Aniston’s — has been trending for years. 

We love this pair by Rag & Bone, which are comfy yet chic, and make the perfect match for your sneakers, loafers, and slides. Their ever-so-slightly loose fit is also a plus for those days when our weight fluctuates — something that can be more common for older women, who may see a change in their body shape with age. 

No reviews yet — yours could be the first!

Good American Always Fits Good Jeans

Best black jeans for women over 50
Best Jeans for Women Over 50
Good American

Buy from Good American, $159

Why we like them:

  • Limitless four-way stretch
  • Go with everything
  • Gap-proof waist

Similar to a black dress, a solid pair of black jeans can be a girl’s best friend. We’re enamoured with this pair from Good American, partially because of the gap-proof waistband but also because they’re extra stretchy. Hitting right at the ankle, the high-rise style is exactly what we want to throw on when the weekend hits and we need to look cute but casual. Since they’re in a black wash, they can go with all types of tops, and depending on what shoe you wear, you can dress them up or down.

One happy customer said they, “live up to their name” and are “flattering.” We couldn’t agree more!

Spanx Jean-ish Leggings

Best jean leggings for women over 50
best leggings

Buy from Nordstrom, $98

Why we like them:

  • Come in a dark rinse or black
  • Available in regular and plus sizes
  • Washer and dryer safe

Designed with skinny jeans in mind, these jeggings by Spanx will give you that same sleek look, but with much more freedom of movement. Choose from a dark denim wash or black — both options really look like actual pants! The faux front and back pockets add to the illusion, though the stretchy elastic waist will remind you that these were crafted for comfort. Pair with a tunic and flats as shown in the photo, or with a chunky sweater and ankle boots when the cooler weather strikes.

One fan called these jeggings “the most comfortable work appropriate pants EVER,” and said they “look like jeans with the comfort of leggings.”

Pilcro The Skipper Wide-Leg Jeans

Best wide-leg jeans for women over 50
best jeans for women over 50

Buy from Anthropologie, $130

Why we like them:

  • Available in standard, plus, tall, and petite sizes
  • Come in dark and medium washes
  • Relaxed fit

Skinny jeans are great, but for days when your legs want a bit more breathability, a wide-leg jean is the way to go. Relaxed, yet stylish, this pair by Pilcro is our pick when it comes to a comfortable, swingy jean that’s just begging to be worn with both billowy blouses and fitted tanks, along with basically any shoe in your closet. The fitted waist and hip-hugging thighs keep them looking tailored, while the knee-level flare gives them that signature carefree vibe. The best part about these jeans? They come in standard, plus, tall, and petite sizes, and in both dark and medium washes.

One fan called these jeans “stretchy and PERFECT!,” saying they’re “versatile for dressing up or down” and that she “cannot wait to wear with booties and a sweater out to do fall things.” Most importantly, she said they make her feel “super confident!”

7 For All Mankind High Waist Ankle Skinny Jeans

Best gray jeans for women over 50
best jeans for women over 50

Buy from ShopBop, $189

Why we like them:

  • Neutral gray color
  • High waist
  • Comfortable, lived-in feel

When you want a neutral that isn’t the traditional blue or black, a cool gray jean is a great alternative. You really can’t go wrong with these beauties by 7 For All Mankind, which have a comfy high waist and whiskered detailing for a bit of texture. More than that, however, they have a lived-in feel that’s still elegant, making them a perfect choice for women over 50 who want to avoid skewing too juvenile with their fashion choices. 

One happy Nordstrom shopper said she ordered them because “they seemed extremely stretchy, and they are!” She went on to say they’re made from a “very soft, good quality material” and are “very high-rise, but flattering.”

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