One Week Till Italy: What to Wear for Three Weeks in Shoulder Season?

Depending on where you will be, you might run into some rain - a waterproof windbreaker might be worth having, or a small folding umbrella (although the umbrella vendors will appear out of nowhere at the first raindrop). If you will be in hill towns, evenings can be a little chilly but your scarf and sweater should be sufficient. What about a money belt, or are you just concerned about clothing? Are you including what you will wear on the plane (1 bra/3 panties seems a little light, one more set won't take much room). I lived out of a 21" carryon and a daypack for 3 months, so I appreciate traveling light.

Are your Toms the only shoes you will have? I love my Toms, but they are definitely not the shoes I would take, especially as my only pair of shoes. I also agree that you might consider having two bras with you (your strap could break on one) and an additional pair of panties, as they don't take up much room.

Is this in addition to what you are wearing on the plane? What part of Italy are you visiting? We are leaving in 2 weeks for Rome/Umbria/Vietri and I am only planning on bringing 1 pair of pants (wearing on the plane) and bringing 2 skirts because temps are supposed to be high 70's or 80. What you are bringing would be too hot for me, but I am pretty warm blooded. I also prefer to bring knit tops (of varying sleeve-lengths and weights, depending on the weather) instead of blouses because I don't like to iron.

I'm going to Italy (Puglia) in October and will take at least one pair of capris, a tank top and some walking sandals, in addition to long pants & fleece and Privos (and a light rain jacket). I have heard of really hot spells in the middle of October, but I will also be prepared for cooler weather. I guess it depends on what part of Italy you will be visiting.

I am leaving in a week and temps seem to range from Mid 80's to lows in the high 40's for my Rome/Venice trip - I think you have a good start but like others HIGHLY suggest another pair of shoes for your poor feet on all of that uneven cobblestone. Personally - I have a pair of Sass sandals and Tsubos that are flats (really awesome leather shoes that have great grips, support and moisture barriers/antimicrobial protection).
As I am packing light as well - maybe least 2-3 bras (if one is drying from washing, one is wearing. Maybe a sports bra (would work under the sweater and does not take up as much space/ wear on the plane trip). Any thoughts on a long say black maxi skirt? Its versatile, cotton blend (for quick washing, rolls small and away and does not wrinkle horribly) and sounds like it would go well with your clothing choices, plus being long it would still allow you to get in to many of the sites/dining that have dress code requirements. Fun travels!

I have been in Verona and Venice for the last ten days and wish I would have brought cooler clothes for the warm (and humid) weather. Sundresses and cardigans are definitely getting more use than my cute jeans! I also love TOMS, but even my perfectly broken in shoes gave me blisters in Venice and I wish I had another pair with me. On that note, don't forget to pack the blister pad bandaid type things! They are about 7 euros here for 4, and at home a couple dollars for 6!