I just came back from my Germany and Florence trip.
Florence street fashion surprised me:
Skinnies everywhere, the only straight leg pants and jeans were worn by older women and I did not see any flares except a couple in a store window. Those were white and embellished with crystals.
Not much hem-rolling either.
A lot of dark colored, sheer hose worn by women of all ages, but especially young women, with skirts, dresses and shorts.
Quite a few knee-high and over-the-knee boots in lighter weights with skirts and dresses (and dark hose).
Dark Sneakers were also worn a lot.
Dresses and skirts were short, not a midi in sight.

A few young men were wearing dropped-crotch jeans.
My favorite was a guy who wore loafers with large metal buckles with his cropped dropped-crotch jeans and sported a Samurai hair-do.
The Samurai hairstyle seems quite popular with younger men.

Shopping was a disappointment. My friend was looking for a flowy below-the-knee skirt and I wasn't looking for anything specific, but thought I might see something I can't live without.
At first, we had no luck finding a longer skirt anywhere. Then we found a couple, but the largest sizes that store carries is a US 8 equivalent. My friend is a 12. We ran into that problem a lot. Many stores don't seem to carry inventory larger than size US 8 at best.
I saw a dress I liked at Louis Vuitton, but a 6000 Euro price tag was a bit of a turn-off
I bought a pair of black Gucci flats and a white Missoni knit blazer

But the company, food and wine were good, so it doesn't really matter that I came home almost empty handed