Madewell Jeans for Women Over 50: Are They Worth It?
I’ve posted a lot about jeans through the years, but what can I say? I love them! I think our needs are pretty simple. We all want jeans that actually fit our bodies, feel comfortable, and still look modern. Is that too much to ask? Madewell has built a reputation for making denim with great fabrics, stylish cuts, and sizes that include petite, tall, and curvy options. But are they worth the price tag if you’re over 50? Let’s break down some of their most popular styles so you can decide if these jeans deserve a spot in your closet.
Madewell Superwide Leg Drawstring Jeans

I linked these Superwide Leg Drawstring Jeans earlier this year and talked myself into ordering them. Lol! They were slightly too big for me through the hips, so I recommend sizing down. Otherwise, I think they are so cute!
The Longline Straight Jean in Greendale Wash
Love a good straight leg jean? These Straight Jeans are for you! They are cut with extra length, which makes them perfect if you’re taller or like to wear a little heel. The straight silhouette is modern without being too trendy, and the Greendale wash is that versatile mid-blue we all reach for again and again. They’re polished enough to wear with a blazer, but still casual with sneakers.
- Long inseam for taller women
- Straight cut that flatters many body types
- Versatile medium-blue wash
- Great dressed up or down
The Cleo Straight Jean
The Cleo is another straight-leg option, but with a slightly cropped hem that shows off your shoes. If you love ankle boots or loafers, this jean lets them shine. The straight leg is forgiving through the thighs, so it’s comfortable without feeling sloppy. LOVE the front pockets
- Cropped straight leg for showing off shoes
- Comfortable through the hips and thighs
- Works well with ankle boots and flats
- Clean, modern silhouette
The Superwide Leg Jean
Now, I know that wide-legs aren’t for everyone, but these Superwide Leg Jeans make a statement. The superwide cut is dramatic and flowy, almost trouser-like, which can actually elongate the legs if styled right. Pair them with a fitted top or blazer to balance out the volume.
- Extra-wide silhouette
- Flowy and elongating
- Great option if you like dramatic styles
- Looks best with a fitted top
The Perfect Vintage Wide-Leg Jean
These Wide-Leg Jeans give you the wide-leg trend in a more wearable way. The high-rise and vintage-inspired shape flatter the waist and smooth the tummy area, while the wide leg makes them modern and on-trend. They’re easier to style than the superwide version, but still give you that relaxed, fashion-forward vibe.
- High-rise waist for a flattering fit
- Wide leg with vintage inspiration
- Easier to style than dramatic wide cuts
- Trendy yet wearable
The Pencil Jean
Some of you were excited to hear skinny jeans are back! Think of this one as the grown-up skinny. The Pencil Jean is slim through the leg but not skin-tight, which makes it a great choice if you’ve been missing the structure of skinnies without the squeeze. Easy to tuck into boots and flattering on just about every body type.
- Slim but not super tight
- Great alternative to skinny jeans
- Easy to tuck into tall boots
- Structured, flattering fit
The Relaxed Bootcut Jean
Bootcut jeans are back, and this relaxed version is perfect if you like a little flare without going full-on retro. The leg opening balances out hips and thighs beautifully, which is why bootcut styles have always been so flattering. Pair them with boots or sneakers for everyday wear.
- Relaxed bootcut silhouette
- Balances out curves at the hip
- Comfortable fit
- Great for everyday styling
The Vintage Flare Jean
If you like a true 70s-inspired look, these vintage flares are for you! They have a high waist and fitted hip that flow into a fuller flare, giving you long legs for days. A little dramatic, but so fun with platform shoes or heeled boots.
- True flare silhouette
- High-rise waist flatters the tummy
- Retro-inspired style
- Best with heels or platforms
The Curvy Perfect Vintage Wide-Leg Jean
Madewell’s curvy fit line is a lifesaver if you struggle with gapping at the waist. These wide-leg jeans are cut to fit fuller hips and thighs, but with a snugger waist so you don’t have to constantly tug them up. These would be a flattering choice if you’ve got curves and still want to try the wide-leg trend.
- Designed for curvy body types
- No waist gapping
- Wide-leg style with a vintage feel
- Comfortable and flattering
The Flared Wide-Leg Crop Jean
These are one of my faves. Cropped wide-legs are fun if you want something different. These give you a flared, wide-leg look but with a shorter hem that shows off ankle boots or sneakers. They’re trendy and playful, best for casual days when you don’t want basic blue jeans.
- Cropped length shows off your shoes
- Wide-leg with flare for drama
- Playful and trendy style
- Great for casual outfits
So, are Madewell jeans worth it for women over 50? I’d say yes if you’re looking for stylish denim that’s modern but still wearable. The cuts are flattering, the fabrics have enough stretch to be comfortable, and the size options (including curvy, petite, and tall) make them more versatile than some brands. What do you think?
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☺️ Lots of styles, but I guess they really like wide-leg styles!
:} Lots of good options!
=) I have never met a Madewell jean I did not like. lol They are my favorites.