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The Worst Jeans Mistakes for Women Over 50

Our fashion expert solves your biggest denim dilemmas


jeans and people wearing jeans, with 'x' marks to note the undesirable qualities of some pairs
(From left) Do sport straight-leg jeans like actress Naomi Watts but don't wear faded, ripped or whiskered denim.
AARP (Getty Images, 5; Gap Factory)

You’re never too old to wear jeans. They make mature women of every size and shape feel sexy, cool, edgy and even comfy. At their best, jeans are the secret to making any outfit sizzle, day or night. They can be chic, polished or casual, whether you pair them with a fancy blouse, ballet flats, a blazer and loafers, or a striped tee and sneakers. What’s not to love?

These days there’s a much more extensive range of classic and trendy jeans, so there’s no reason for women to hang on to their skinny jeans or wear an old, distressed default pair. You’re not alone. Here are the top mistakes to avoid — and solutions for wearing your denim best.

models wearing wide-leg jeans
(From left) Find flattering wide-leg jeans: Old Navy Women High-Waisted Wow Crop Wide-Leg Jeans in Faded Medium Wash; Gap Women High Rise Stride Wide-Leg Ankle Jeans in Medium Wash; Sonoma Goods For Life Women’s Relaxed-Fit Wide-Leg Ankle Jeans in Dark Wash.
AARP (Old Navy, Gap, Kohl’s)

Mistake #1: Choosing the wrong wide-leg jeans.

For the first time in years, grownup women are swaggering around in “big jeans.” The styles range from wide legs to an overall baggy look, plus “barrel” and “horseshoe” shapes that curve out at the hips and thighs. Many women say their thighs, calves and ankles finally have wiggle room, and they can slip their jeans on and off without a struggle. Not all pairs are flattering, however.

I’m a fashion editor, stylist and personal shopper for women over 50 who are asking, “Are wide-leg jeans a good look for me?” Here’s the short answer: If you love the roominess of midi or maxi skirts, you can wear wide-leg jeans. But skip the bendy comma shapes and baggies (they help no one!), and opt for a style that mimics an A-line midi skirt.

Choose a wide-leg jean — cropped or ankle length — that starts out trim at the waist and hip and gradually flows to its widest point at the hem. You can’t miss with styles like the Old Navy Women High-Waisted Wow Crop Wide-Leg Jeans in Faded Medium Wash, Black Mambo or White Wash ($35, oldnavy.gap.com), Sonoma Goods For Life Women’s Relaxed-Fit Wide-Leg Ankle Jeans in Dark Wash ($34, kohls.com) and Gap Women High Rise Stride Wide-Leg Ankle Jeans in Medium Wash or Black ($90, gap.com). 

models wearing straight-leg-jeans
(From left) Opt for straight-leg jeans: Venus Women’s Audrey Straight Leg Jeans in Medium Wash; Lee Women’s Relaxed Fit Straight-Leg Jeans in Meridian; Gap Factory Women Mid Rise Classic Straight Jeans in Dark Nieves
AARP (Target, Kohl’s, Gap Factory)

Mistake #2: Staying loyal to skintight skinny jeans.

If wide-leg jeans hold no appeal for you, bootcut styles are too been-there-done-that, and your closet is filled with old faithful skinny jeans … pause. The allure of skinny jeans is the practically painted-on fit that reveals as much about your shape as a swimsuit. Is that always a good idea? No. The extreme definition can also reveal every bump, bulge and extra pound. How can skinny jeans be comfy when the circulation in your legs is being squeezed, compressed and compromised? Fans of skinnies think the tight look streamlines their body like shapewear, but who are we kidding? We’re revealing more than necessary.

It’s time to move on to straight-leg jeans like the Venus Women’s Audrey Straight Leg Jeans in Medium Wash ($50, target.com), Lee Women’s Relaxed Fit Straight-Leg Jeans in Meridian, Bewitched or Jaded ($35, kohls.com) and Gap Factory Women Mid Rise Classic Straight Jeans in Dark Nieves, Black Wash or Medium Masco ($36, gapfactory.com). The snug fit from waist to hip and consistent width from top to bottom will provide a slim feel, a sleek line, and a much classier look. Yes, jeans pros predict that skinnies are coming back, but ignore them. Still skeptical? Know that “straights” are always stylish regardless of trends. Plus, they come in a range of widths, from slim to relaxed, and fits, from regular to curvy, for more room at the hips and rear.

jeans in appropriate lengths
(From left) Pick the correct inseam: Mother Petites The Lil’ Hustler High Rise Ankle Jeans in Fairest of Them All; Madewell Women’s Petite Kick Out Crop Jeans in Lenoir Wash.
AARP (Bloomingdale’s, Madewell)

Mistake #3: Not taking the inseam length seriously.

As a personal shopper who spends a lot of time watching clients try on jeans, I see plenty of inseam mistakes. They think the regular store-bought length is “good enough,” and they don’t want to spend extra on tailoring. The most common tip-offs are getting a pant hem stuck in the back of your shoe as you walk (typical for ankle jeans), tripping over the hem (standard in full-length jeans worn with flats), and sloppy puddling at the vamp of your shoes (often seen in full-length jeans worn with low heels or wedges).

Here’s my take: Tweaking the hem length at the tailor or at home is almost always necessary. Decide whether you prefer a neat straight hem, which looks more polished, or a frayed hem, which adds a subtle edge to jeans. (You can DIY a trim and get a frayed effect without sewing.) A tailor can convert frays to neat in minutes, and vice versa.

Say no to cuffs as a zero-tailoring length solution. I know it’s easy to roll up a cuff on jeans, and trendy to turn up large cuffs on wide-leg pants, but … don’t. It shortens the leg.

If you’re 5 foot 3 or under, take advantage of petite sizing in jeans, which gets the length and knee “indent” (where they hit on the knee) right. Great petite styles include the Banana Republic High-Rise Straight Ankle Jean in Medium Wash or White, Petite ($100, bananarepublic.gap.com), Madewell Women’s Petite Kick Out Crop Jeans in Lenoir Wash or Pure White ($138, madewell.com) and Mother Petites The Lil’ Hustler High Rise Ankle Jeans in Fairest of Them All ($228, bloomingdales.com).

models wearing jeans in fashionable colors
(From left) Wear the right denim wash: Levi’s Women’s High-Rise Wedgie Straight Cropped Jeans in Max Effort; June + Vie Plus Size Curvie Fit Wide-Leg Jeans in Dark Blue; Everlane Women The Way-High Sailor Jean in Coal.
AARP (Target, Macy’s, Everlane)

Mistake #4: Wearing ripped jeans and outdated washes.

Remember pre-distressed jeans with rips, holes at the knee, extreme fades and a shredded look? Gone! Whiskering? No more! Coated jeans? History! The cycle of trendy washes keeps changing, and wearing outdated colors and finishes is a major mistake. A classic, even-toned, medium-to-dark-blue jean, like the Levi’s Women’s High-Rise Wedgie Straight Cropped Jeans in Max Effort ($70, target.com) and June + Vie Plus Size Curvie Fit Wide-Leg Jeans in Dark Blue ($58, macys.com), never goes out of style.

Are you over buying another pair of blue jeans? Try a solid white — no worries, these days they’re opaque, not see-through — like Loft High Rise Wide Leg Crop Jeans in White ($48, loft.com), or a black jean like Everlane Women The Way-High Sailor Jean in Coal ($148, everlane.com). Both have a sophisticated look, especially when paired with more black or white or other neutrals like tan, gray or camel, and they work year-round. Try white jeans with a black V-neck and loafer mules for an elegant effect, or black jeans with a crisp white shirt and black sandals for a summer outfit that’s easy yet pulled together.

Mistake #5: Sorry, your jeans are a bad fit.

It’s easy to pinpoint a bad fit on other women, but it’s harder to do so on yourself. Those jeans you loved at first glance may be awful in the real world. Remember, others see you from all angles! Standing in front of a mirror before removing the tags isn’t enough. Wear the jeans while you watch TV or work from home. Walk around the house, squat, bend, twist, reach, sit and stretch. Only then can you get a proper evaluation.

  • Do your jeans need a belt to stay put? Do you need to tug the waistband up whenever you sit and stand? The rise is too low or the size is wrong for you.
  • Is your muffin top spilling over the tops of your hi-rise jeans? Look for a lower hi-rise rather an extra hi-rise style.
  • Are your jeans sagging or too tight in the crotch? You need a bigger size or another style.
  • Are the back pockets placed high or low? Higher is better — it makes your legs look longer and gives your rear end a lifted, firm look.
  • Does the zipper gape or not close fully? You need a different rise or a pull with a wide stretch waistband.
  • Do the back of your jeans feature horizontal pulling (also known as “drag lines”) across the backs of your thighs? The waistband of your jeans may be too loose, or the thighs may be too tight.

Don’t settle and say, “I’ll wear an oversized shirt.” You deserve a better jean.

models wearing jeans that fit
(From left) Choose flat-front pull-ons: Gloria Vanderbilt Women’s Amanda Pull-On Straight Jeans in Murray; Croft & Barrow Women’s Classic Pull-On Jeans in Medium Wash.
AARP (Kohl’s, 2)

Mistake #6: Wearing jeans that are not in sync with your tops.

Here’s a fashion chicken-and-egg dilemma: When deciding what to wear, which comes first, your jeans or your top? Most women pick the top and then the jeans. That brings up two mistakes: wearing untucked tops and tunics with hi-rise jeans, and shorter tops with medium rises. It should be the other way around.

Here’s why. Medium-rise jeans sit lower on the torso, right at or just below the belly button. It’s an ideal rise for relaxed tops, longer untucked tees, semi-tucks and tunics. Hi-rise jeans sit just above the belly button or higher. Waist definition is a key part of the look, and this rise works best with tucked-in tops, bodysuits, cropped tops, and jackets that hover just over the waistband and emphasize the waist.

Some women who only wear long, untucked tops buy high-waist jeans because “it holds me in better.” My advice? You don’t need the extra bulk of a working zip-front placket, belt loops and pockets with longer tops. Instead, choose a pull-on style like the Woman Within Women’s Plus Size Flex-Fit Pull On Denim Capri in Medium Stonewash, Indigo or Black ($34, target.com), Croft & Barrow Women’s Classic Pull-On Jeans in Medium Wash or Dark Wash ($35, kohls.com)

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