I wear mine on cold or rainy days when it's nice to have the bill of the cap keeping the crap out of your face/eyes. basically means I wore one in every single cyclocross race this year as well as throughout the year when conditions dictate.

I also wear one after every race/ride if I'm hanging out afterwards. It's what all the fat, wannabe racers/posing hipsters wear.

My team one gets worn the most now, but clashes with everything except the team kit....