Kids (1995)

Director: Larry Clark

The '90s was arguably one of the more shambolic era for trends. Wide-leg pants, slouchy shirts, and burgeoning streetwear brands reigned "supreme," but the titular kids in this film made not giving a shit look cool. These urban urchins threw on whatever was near them when they woke up, then went out to cause more ruckus. It also didn't hurt to roll with dearly departed skater Harold Hunter.