You know what I always think looks really chic? When someone is dressed timelessly, but with just one element that brings the outfit bang up to date. A look that is 90% personal style, 10% zeitgeist. That is such a good formula.
Being head-to-toe in new trends is not cool these days. It can look a little overeager, and your clothes end up wearing you rather than the other way around. But a look that plays it completely classic can feel a little safe.