Loaded heels almost always occur when you are wearing jeans and it is wet and/or raining outside. The bottom of each pant leg becomes damp, causing discomfort in the heel and ankle area, and causing the dampened areas of you jeans to rip over time.
-Aaron walked to school in the rain, and got loaded heels along the way.
Child 1: 'Did you walk to the sockhop last night?'
Child 2: 'Yeah, I did.'
Child 1: 'But it was raining, were your heels loaded?'
Child 2: 'Yeah bro, fully loaded. It was mad annoying.'