How many berets do I have? Five. You already know I am obsessed with hats and I think the beret is the most wearable of all. From classic black to sequins to knit to topped with a pom pom, the beret love is in full force for Fall. What's great is the beret spans decades; wear with wide-legged jeans for a sassy '70s look, top off a sexy pencil skirt with one for a demure '50s vibe, ...