Dressing privately, or appearing to do so with fashion it’s always hard to tell what’s truly private and what’s a private look. Tailored clothes are hard to pull off—they look too aggressively status-hungry, too much like sartorial armor. You have to look like you’re dressing for yourself, like you dress like this at home. You can’t appear to be trying too hard. You have to seem swept up in the great experience of your great, original life.