It helps to know how to break the rules:
The crucial factor [in being cool], says a forthcoming study in the Journal of Consumer Research, is the demonstration of autonomy. Refusal to comply with established norms signals that you have confidence and independence, that you’re not concerned with the expectations of others. But this only works if autonomy is considered appropriate—if the norm being defied seems unnecessary, illegitimate, or repressive. Being cool isn’t just about breaking rules. It’s about breaking the right rules in the right context.
In one experiment, participants were asked to evaluate an advertisement for a brand that advocated either breaking or following a dress code. When the participants were told that the dress code existed for an “illegitimate” reason—to honor a corrupt dictator—breaking it was perceived as cool. Conversely, when it existed for a “legitimate” reason—to honor war veterans—breaking the code wasn’t cool anymore. Rule-breaking is cool, researchers hypothesized, when it hits a sweet spot of moderate, but not extreme, unconventionality.