the jess edit

How to Style Baggy Jeans

Photo: Clément Pascal

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Never underestimate the power of good denim. The Cut’s fashion director, Jessica Willis builds many of her outfits around it. The key? Proportions. Think of these jeans as a relaxed pair of trousers, just in jean form, she says.

Willis would describe her approach to style as three things: timeless, functional, and edgy. So a good outfit needs to include an element of each. In this week’s installment of “The Jess Edit,” Willis we breaks down the anatomy of how to style a baggy jean.


Start With a Hero Piece: The Baggy Jean

“Wearing baggy jeans is the most comfortable thing you can do,” says Willis. And for her, comfort also means low rise. “You can eat, expand, and still feel good in your clothes,” Willis says. But not too low rise; we aren’t talking about Paris Hilton in the early aughts — we mean pants that sit right on the hip.


Don’t be afraid of tailoring

There’s an art to wearing the baggy jean, and if you have shorter legs, it starts with tailoring. “Don’t be afraid to get your clothes tailored,” Willis explains. It’s quite easy. You can trust your neighborhood dry cleaners for a simple hem. If you need suggestions, head right this way. If you’re not sure what length to hem them, Willis suggests the back of the jeans should just kiss the floor but not drag. That way, they will show off your shoes as well.


Play with proportions but always highlight your waist

“If you prefer to wear a baggy shirt, make sure you tuck it in so you can see your waist,” she explains. “If the shirt is too long and the jeans are baggy, it will make your legs look short and throw off the proportions.”

Tuck your shirt into your waistband, and if you need a little extra hold, Willis suggests adding a belt: “You don’t want the look to swallow your body.”


When in doubt, oversize

In this case, the oversize blazer keeps you warm in the office AC and the sharp shoulders will frame the outfit. Plus this oversize bag will hold everything you need for casual Fridays, Willis’s is from Loewe.


Don’t be afraid of flip-flops

We know what you are going to say, and we normally would agree: As New Yorkers, we typically wouldn’t be caught dead in flip-flops without a beach in sight. But these are from the Row and are a way to make any outfit look cool. They are also made of leather and have a slight platform, which is kind of like a heel. Remember Rocketdogs from the ’90s? That, but chic.

Get the look

Made from 100 percent cotton, these jeans will not only check off the ideal baggy silhouette you’re coveting but also have the certification of the Global Organic Textile Standard (GOTS).

Available in sizes 22–32.

Just because a jean is baggy doesn’t mean your butt will disappear under the fabric. Still Here purposely designed these jeans to be baggy and flattering on your derriere.

Available in sizes 22–32. .

If you want to see if the baggy trend is a good fit for your aesthetic and lifestyle, try out this under $55 option from Asos. Affordable and gets the job done.

Available in sizes 14–24.

How to Style Baggy Jeans