Britney Spears Hits Teddy’s in Hollywood for 2006 Night Out

Britney Spears emerged from her car like a tabloid fever dream—half rockstar, half rebellious prep. The outfit? A loose checkered shirt, striped tie, and micro black skirt, all anchored by black high-heeled sandals that clicked against the pavement with paparazzi-prompted urgency. It was the kind of look that didn’t ask for attention—it demanded it.

The styling was pure mid-2000s chaos: part post-divorce liberation, part pop princess off-duty. Her hair, tousled and unstyled, added to the rawness of the moment. No glam squad polish, no red carpet restraint—just Britney, unfiltered, stepping into the night.