In my attempt to refine my wardrobe and hone my personal style into something more cohesive and less manic, I'm starting to realize I'll probably end up repeating things more often than I might have been comfortable with before. The fact that they will be in different outfits with other pieces doesn't seem to fully allay my anxiety about it, so I'd really like to know what is typical for others. Certain things like a black pencil skirt, black trousers, or a button down in any color are naturally less conspicuous and not likely to be noticed. But other items like a leather Moto or red skinny pants seem like they would stand out if I wore them too often. But how often is too often? What are your thoughts on this?