How To Wear Cropped Wide-Leg Pants Now and Later

Truth be told, I didn’t buy into this cropped, wide-leg thing for a long time. When they first arrived on the scene, most of my clients felt dumpy and not at all stylish wearing them. The only shoes I felt looked decent with them was a pair of low-contrast, pointy-toe heels. Fast forward a couple of years and the trend has worn me down. I attribute it to skinny denim fatigue. Now, I wear them myself (oh, it’s so amazing to have pants on that don’t squeeze my legs!) and have many of my clients give them a day in court.

They aren’t as easily versatile as some other denim silhouettes out there, but they are more versatile than you would think. They key is selecting a pair that is high-waisted, tucking your top or wearing with a shorter/more cropped top, and styling it with the right shoe. Here are a three ways to do this trend where it feels purposeful and chic and…dare I say…flattering?


Go sporty.

Wear with a great pair of kicks and a casual top….

But keep the kicks a light color — white, taupe, etc. Avoid black or dark sneakers. Black/dark colors cause the area of your body you wear it on to recede/look smaller. Because the pants have volume, your feet in dark shoes will look disproportionately small. Try it. It’s weird. And sorry, no socks. Some people can rock socks with the wide-leg crops, but it can go so wrong so I generally don’t recommend doing it. #coldankles #sufferforfashion

Jeans from TSALT | The rest from The Hive and The Shoe Hive


French chic it up.

This look is with boots, but you need a specific type of boot to pull the look off: a sock bootie. These are boots that have a dressier vibe. They have a pointy toe, block or stiletto heel, and look like a pump that has a sock attached to the top part of the shoe. The shoe hugs your ankle all the way up your ankle like a sock.

Layer this look with a jacket and accessorize with a scarf. Perfect for the the transition from winter to spring.

Jeans from TSALT | The rest from The Hive and The Shoe Hive


Go classic.

Wear with a low-contrast pair of flats (pointy toe, please!) to lengthen your leg line. This is a shoe that blends with your skin instead of contrasting with it.

Keep the rest of your look tailored, classic, and pretty. Don’t forget to tuck in that top!

Jeans from TSALT | The rest from The Hive and The Shoe Hive


📸 :: Emma McAlary


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Founder, Chief Stylist | DC Style Factory
Rosana has 18 years of fashion and retail experience. Her team has worked on more than 1,500 closets and wardrobes since she launched DC Style Factory 10 years ago. She has been featured by the New York Times, The Washington Post, NPR, Washingtonian Magazine, Northern Virginia Magazine, and more. Her clients include U.S. politicians, lobbyists, authors, lawyers, and corporate executives.

DC Style Factory is a personal shopping and styling service for men and women looking to add polish and individuality to their wardrobes. We believe personal style is for anyone who wants it — regardless of age, size or budget.

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