The concept of “trying too hard” irks me. People are constantly being criticized for putting forth minimal effort, and yet we censure them for being overly enthusiastic, too. Talk about a lose-lose proposition.

And yet, I’ve gotten several reader questions about “trying too hard” stylistically, and I understand why. When I was 13, I felt certain that simply OWNING and WEARING cool clothes would make me cool … but when I got my hands on an entire Esprit ensemble and wore it to school, I was still shunned. And the feeling I had? Trying too hard. Specifically trying too hard to fit into a group that didn’t want me, trying too hard to adopt a style that had nothing to do with my own tastes, trying too hard to be someone I’d never be. read more