Been awhile since someone put up a suitsupply pic just because, so here is what I'm wearing today. Napoli that I bought in spring 2012. (excuse the slightly fuzzy pic, I am teaching my 3.5yo girls to hold the camera steady). Yes, I know that I need to pull my pants up. Cheers.
I'd put the crazy socks in the love-it-or-hate-it category, along with PS's (for some), wrist bands, suspenders, lapel pins, and hats. I like some color on my ankles from time to time, but I stick to standard colors if I have an important client meeting. All about environment, IMO.
Depends on if you would rather wear a herringbone coat or a textured coat. FWIW, I have a brown herringbone tweed SC , and I feel like I have to wear only solid shirts underneath. I also have a grey tweed SC that is just rough textured like the Lazio you quote, and it's a little easier to change up the shirts.