Messy Updo. This is where you just pile it all up on top of your head for a bedhead look that is sexy and elegant. Imperfection is the runway look this season when it comes to messy hair. You can do this with a ponytail, bun, or a chignon, and for any flyaways or strays, run the strands around your curling iron for a sexy messy look. Spritz some extra hold spray and your messy look will last all night long.