The Oversized Cuffed Pants Trend: How to Wear It For Women Over 50

I’m noticing a trend in stores that I predict will be big this spring and summer: the oversized cuffed pants trend. We’ve already seen this look with denim jeans, where rolled up 5-6″ cuff creates a striking contrast.

Cinq à Sept Benji Topstitch Cuff Jeans, $295

Something like these Cinq à Sept Benji Topstitch Cuff Jeans can be tricky to pull off. If the oversized cuff sits too high or too low on your leg, it can end up cutting you off in the wrong place, making you appear shorter. In some cases, they just might not be flattering. Personally, I find them a bit flashy (and honestly, I don’t need any extra attention these days). I would feel like I’m trying too hard to look younger in these jeans. Of course, if you can pull them off, more power to you! I just think they can be difficult to wear.

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A More Subtle Approach to the Cuff Trend

That said, I’ve noticed a more subtle version of this cuff trend emerging, especially with solid-color jeans or trousers. In the case of these Veronica Beard Dylan Cuffed Herringbone High Waist Relaxed Straight Leg Pants, the rolled-up cuff blends seamlessly into the fabric, making it a more understated detail. This version of the trend feels much more refined and flattering, as the cuff doesn’t compete for attention but rather complements the overall look.

My Thoughts On The Trend

Do we really need someone else to roll up our pants for us? Personally, I’ve always been a bit skeptical of fashion that seems to force a casual look—like permanently rolled sleeves on shirts or boyfriend jackets. I feel the same way about fake rolls on pants. However, I do find that a neatly ironed cuff works much better than trying to roll them up yourself. When it comes to cuffed pants, it’s best not to go the DIY route. A perfectly placed or stitched-down cuff gives a cleaner, more polished look.

Frances Valentine Smarty Cuffed Jeans

Frances Valentine Smarty Cuffed Jeans (available in pink, white or green), $278

The Cuffed Pants Trend for Women Over 50

One of the best styles for women over 50 is a pair of pants that are fitted through the waist and cropped, like this pair from Frances Valentine. These pants are a welcome alternative to shorts or skirts during spring and summer and are easy to style. They pair well with nearly any shoe, whether it’s high heels, block heels, or flats. Wide leg pants can be difficult to wear because sometimes you need to wear a higher heel, but cropped versions resolve that dilemma. And your styling options are easy and practically endless. You can tuck in a top, tee or blouse or layer a sweater or jacket over the flat waistband of these pants.

Use code FVLAUREN17 to save 17% at Frances Valentine.

Shop the Trend

Here are some of the best cuffed pants I found for women over 50, at a variety of prices ranging from $4,000 to only $49!

Valentino Garavani Toute La V Metallic Jacquard Pants

Valentino Garavani Toute La V Metallic Jacquard Pants, $4,000

You could spend $4000 on a pair of cuffed pants! I’m only showing you these because some of the top designers are offering them this season.

Cinq à Sept Winona Double Belt Stretch Brushed Cotton Twill Pants, $345

You can get a little trendy with the look. Try these lightweight utilitarian cuffed pants with multiple belts to add (or subtract) to give you styling options.

Joe’s The Trixie Cuff High Waist Wide Leg Trouser, $198

These more moderately priced Joe’s jeans in Creme Brulee are a perfect combination of denim with trouser-style pockets in front. These can be your go-to pants for spring and summer.

1.STATE Women’s Denim Roll-Cuff Wide-Leg Jeans, now $55.59

Or get a very similar look for less with these Macy’s 1.STATE pair that are currently on sale.

Halogen® Cuff Wide Leg Pants, now $49.50

The oversized cuff pant can go to the office, too. This pair in grey are a very subtle way to wear the trend this season.

Do you like the oversized cuff pants trend? Or are you wondering what is the purpose? We’d love to hear your thoughts!

Carol Calacci

You may also like to read 5 Fabulous Looks for Women Over 50 from NYFW Fall 2025 and The Best Denim Styles for Women Over 50: Perfect Jeans for Every Shape.

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