Best J.Jill and Chico’s Jeans for Women Over 50 in 2025

Gurls, can we all agree that finding the right pair of jeans after 50 is a bit of a treasure hunt? That’s one of the main reasons I decided on this jeans series. Some are too low, some are too tight, and don’t even get me started on fabrics that feel like cardboard. The good news is that both J.Jill and Chico’s have stepped up with jeans designed for real women’s bodies. These aren’t the trendy pairs you regret buying; they’re jeans you’ll actually reach for in your wardrobe again and again.

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J.Jill and Chico’s Jeans – In Real Life

More J.Jill Jeans for Women Over 50

J.Jill Curvy Fit Straight-Leg Jeans

If you have fuller hips or a smaller waist, these curvy fit jeans will be your new best friend. The straight leg gives a clean silhouette, while the cotton blend fabric has just enough spandex to move with you. Perfect with boots in the fall but they’ll also work with sandals when the weather is warm.

• Curvy-friendly fit with room through the hips
• Straight-leg style that works with any outfit
• Comfortable cotton blend with stretch
• Versatile for year-round wear

J.Jill Boyfriend Jeans

I never had a boyfriend this small, lol. Maybe in middle school! These “boyfriend” jeans are slightly relaxed without looking sloppy. The fit is looser through the thighs with a slightly tapered leg, so they look great cuffed with sneakers or dressed up with a denim jacket and scarf.

• Relaxed fit for everyday comfort
• Tapered leg that flatters without clinging
• Easy to pair with tees, shirts, or sweaters
• Roll up the hem for a casual vibe

J.Jill Curvy Fit Authentic Slim-Leg Jeans

For days when you want a more tailored look, these slim-leg jeans fit the bill. They’re slimmer than a straight cut but not skin-tight, which makes them great with tunics or longer shirts. The curvy fit keeps them comfortable at the waist and hips.

• Slim-leg style for a polished look
• Curvy fit gives comfort at the waist
• Works with longer tops or blouses
• Stretchy cotton blend fabric

J.Jill High-Rise Wide-Leg Ankle Jeans

These wide leg jeans are right on trend without feeling too young. The high rise smooths the waist, and the ankle length is perfect for showing off a cute pair of shoes. Wear them with loafers, sneakers, or ankle boots. They all work!

• High-rise waist gives a smooth fit
• Wide leg jeans that look modern and chic
• Ankle length works for showing off footwear
• Great with tucked-in shirts or cardigans

J.Jill High-Rise Curved Pocket Flare Jeans

Flares are back, and this pair makes them easy to wear. The curved pockets add a nice, subtle detail, and the cotton-spandex blend fabric means you’ll stay comfy all day. Pair with heels or wedges to elongate the legs.

• Flattering high-rise fit
• Flared leg balances curves
• Curved pockets add subtle style
• Stretchy fabrics for comfort

J.Jill Relaxed Boyfriend Jeans

Finally, boyfriend jeans that actually look like a boy might be able to wear them, lol. These are relaxed, which means they’re looser through the legs. These would be easy to wear with sneakers, sandals, or even a chunky cardigan layered on top.

• Relaxed fit with extra comfort
• Looser leg opening for a laid-back feel
• Works well with casual shirts and sweaters
• Perfect for weekends or vacation days

More Chico’s Jeans for Women Over 50

Chico’s Embellished Frayed Flared-Leg Jeans

Chico’s knows gurls need a little fun. The frayed hem and embellishments make them stand out without feeling over the top. They’re a great choice for a night out when you want jeans that don’t feel too basic.

• Embellished detail for a touch of sparkle
• Flared leg adds movement
• Frayed hem for on-trend style
• Dress them up with a blouse or blazer

Chico’s Coated Girlfriend Cropped Flared Jeans

Okay, Fancy! These coated jeans give a leather-like finish, which feels edgy but still wearable. The cropped flare cut makes them easy to pair with boots or heels. They’ll add instant style to your fall outfits without much effort

• Coated finish with a leather look
• Cropped flare silhouette
• Great for dressy casual outfits
• Works with boots or heels

Chico’s Pull-On Cropped Wide-Leg Frayed Jeans

Pull-on jeans are my secret weapon for comfort! No zippers, no fuss, just slip them on and head out the door. The wide leg keeps them modern, and the frayed hem makes them feel fresh. Pair with a blouse or denim jacket for a relaxed but polished outfit.

• Pull-on style for ease and comfort
• Cropped wide leg silhouette
• Frayed hem detail
• Pairs well with shirts or cardigans

Finding jeans that look good and feel good in our 50s, 60s, and beyond doesn’t have to be a struggle. J.Jill and Chico’s both have great collections made with soft fabrics, flattering fits, and plenty of stretch so you can stay comfortable without giving up style!

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