Hardly ever. I live in Winter Wonderland and can rarely go outside in heels without freezing my toes off or falling flat on my *** on the ice. When I get to wear heels outside maybe once or twice a year if I try real hard, and both those times I end up in the middle of a field or running down a dirt road, it's very hard to justify the price tag on designer shoes
I love wearing heels, though, and would wear them around the house until I got a new puppy (it's hard not to step on her, she hasn't learnt to watch out yet) If I lived somewhere warm I'd wear heels every day, I'd never take them off