I agree wholeheartedly with Gaylene's latest comments. I think I come closest to this when I'm wearing something that fits me really well that I feel physically, emotionally and mentally comfortable in. My DVF wrap dress and the Rockstuds come to mind. Or that outfit the other day with the Amber Sun sweater and the tall Frye boots. Or my blue leather moto with just about anything (seriously, that thing makes me feel like a rock star every time).
I'm learning to trust the feel of an item as well as the appearance in the mirror. Some things lie on a person's body just so and contribute to that effortless look. Some *types* of items are particularly well suited to certain people and certain body types. For me, it's structured jackets, and that's why I have so many of them. For other ladies here, it's trousers, or slim jeans, or pencil skirts, or button-front blouses, or drapey knits. When we throw on one of these magical items, it meshes with our personality and style persona and looks effortless.
Very little that looks effortless is truly effortless, and pictures show only a frozen microsecond in time, and they can be endlessly manipulated. It's alllll an illuuuusion!