Britney Spears Halloween Costumes | POPSUGAR Celebrity

Picture it: It’s August 2003, you’re sitting in your living room watching the MTV VMAs, and out comes Spears, chewing gum while belting out “Like a Virgin,” and then pow! Before you know it, she’s making out with Madonna.

What to wear: A semi-wedding dress — make sure the skirt and veil are detachable, so you can reveal the sexy white bustier and short-shorts that you’re wearing underneath. Layer lots of pearls and chains around your neck. Add a “boytoy” belt and white lace gloves. Carry a bouquet of flowers. No matter what you do or who you kiss, make sure you keep the gum in your mouth.