Marilyn Monroe is remembered for a lot of things—a signature platinum coif, an illustrious love life, an infamous scene with a subway grate—but it’s often forgotten that the blonde siren was actually an early pioneer of the boyfriend jean trend. She was spotted wearing them on the set of the 1961 film The Misfits, and since then, various iterations of loose-fitting, slouchy jeans have drifted on and off fashion’s radar. A whopping 47 years later, Katie Holmes notably brought the style back to the forefront when she sported a pair of Tom Cruise’s blues on the streets of NYC in 2008.
The boyfriend jeans of the early aughts were inspired by literally borrowing your boyfriend’s jeans—they were oversized, slouchy and often required a belt. Now, you can find everything from this menswear-inspired style to the more-fitted “girlfriend” silhouette to the latest slouchy slim jean that features a longer, roomier inseam with a tapered leg. All three are totally on-trend, so feel free to go with whatever suits you. Ready to find your new favorite boyfriend blues? Click through the slideshow above to shop our favorite styles of the season.