Supermodel Heidi Klum is the queen of messy updos. Though her hair is loose, it isn't sloppy or unruly -- Klum keeps it under control with simple, strategically placed pins.

It may sound counterintuitive, but perfecting the messy updo is an art best left to an experienced stylist. Homemade messy updos can fall out or look too messy to be dressy.