Instead, take the time and effort to find something both appropriate for the occasion AND suited to your personality and taste

Agreed. I do that too: I've never shown up to a wedding, funeral, first date, whatever in a suit or something. I just wear something that's as neat and appropriate as possible and no one has ever complained to me about what I wear. So that goes for women as well. Just wear something that feels comfortable but is also appropriate enough. Esp. with things like weddings and first dates, it shouldn't be hard, even if it feels unlike you. I mean: it's not like weddings and first dates last for days on end, so you're back in your regular clothes sooner than later.