Pretty soon, you'll find that a certain item or specific outfit will simply work. Don't be afraid to repeat this way of dressing. Pharrell has been rocking this BBC Bee Line cap at every single appearance and video cameo since Mark McNairy put it out, and nobody's mad at it. If you love something or like the way it looks, own that feeling and rock it as often as you want. Congrats, you just unlocked your first "don't give a fuck" achievement.