Ashlee Simpson’s hair was getting downright scraggly in the last few months. It was a hodgepodge of sad, brown and blonde that often seemed to be in a state of disarray. Instead of getting a trim or some fancy hair treatments, Simpson did something drastic two days ago – she chopped off all her hair!

Though it’s a drastic change that a lot of women regret, Ashlee has the perfect face shape to pull it off, and she looks absolutely adorable. We caught up with the singer/actress returning to the Ritz Carlton with 23-month-old son Bronx last night. Mom and son look so cute with their matching hair!

Ashlee’s husband Pete Wentz also aproves; last night he tweeted, “Yah fam headed out tonight stoked! Cute hair mama!” Check out Pete’s cute picture of Ashlee and Bronx at the hair salon!

Long-haired photos were taken in August and September 2010.