I had to delete my account due to a scary and unrelated stalking issue. :-/
Anyway, I want to clarify a few things. Honestly, if I would have known how nasty one particular response I would have received here would be, I wouldn't have even bothered. It's really easy to forget there is a person behind a computer screen, right?
Of course there are frumpy dressers in Italy. Italy has tens of millions of people. Not everyone is a perfect dresser who wears only the most impeccable garments and turns their nose up at everything else all of the time. It would be impossible and, frankly, it's not the message I want to put forth in this guide. It is simply not possible to always look your best (and you shouldn't always have to!), but there is the "bella figura" that still reigns supreme in all aspects of life in Italy.
There is truth in saying that Italian women are known for being "stereotypically" feminine. Without going into details, Italy's Mediterranean culture is part of a larger culture of countries where "men are men and women are women." Whether or not this is right (I, myself, rebel against these stereotypes in almost every aspect of my life) is up to you to decide. I didn't post this to get into a nasty, vitriolic debate about what it means to be a woman. If you feel your best in Chukka boots and a trench coat or with your hair in a mohawk... do you! That is wonderful. Femininity doesn't always mean putting on heels, but in the traditional Italian context, it is not incorrect to say that thee is a certain idea of "what a woman looks like." Whether or not this interpretation of femininity within the Italian context is wrong is not the debate here. It simply is.
This is not an actual, word for word guide. This is not the gospel. It's about aspirational dressing. It's about taking a rule (say, mix rich fabrics with lesser ones) and using it to your advantage to fit your lifestyle and your budget. I am not claiming to be an expert by any means. I am just Italian, and a product of that.
This guide isn't so serious! There is no reason to be insulting, and this forum should be a safe space for all of us to contribute. Otherwise you scare away other people who would like to contribute.
I am not a professional. I don't know how to put "real" guides together. I just wanted to share my observations as someone who is a product of this culture and this idea when it comes to dressing your best. I am not telling anyone they are wrong if they don't dress like this.