Our latest take on a boyfriend fit was inspired by the kind of

old-school cowboy jeans we always wish we could find at a thrift store. With a tall rise that can be worn high at the natural waist or low and slouchy (hello, options), this bootcut style has a cool look, for sure.

We recommend getting these in your usual size—they'll feel tight at first but stretch out juuuuuuust enough after a couple of wears.
Monogramming available for US customers: To have this item embroidered with up to nine letters for $10 (free for Madewell Insiders), please call 866 544 1937.
Premium 100% cotton ringspun denim.
An authentic worn-in dark wash with a cool frayed edge on on the waistband, knee rips and cutoff hems.
Copper hardware; contrast stitching.
Fitted through hip and thigh with a flare leg.
Front rise: 11"; inseam: 25"; leg opening for size 25: 16".
Machine wash.
Import.
Select stores.