Bailey-Chaidez cites Meg Ryan’s bob—worn tousled, curled (think City of Angels), and ironed, depending on the occasion—as a quintessential ‘90s cut. This cut toes the line between shag and ...

but mostly by the short shag haircut made popular by the likes of Rachel Green and Meg Ryan in You've Got Mail. Jenner's ‘90s-inspired cut may have just been for the photoshoot, as other recent ...