How to Dress in Tuscany in Late September Early October and Venice in October

I like your plan. Should get you through everything, although I personally would not bother with a skirt or capris. I stick to three bottoms, max. I would take 2 jeans and one dressier, lighter pant (as I am traveling with that combo now). Don't forget your Smartwool socks!

Be ready for rain. Yesterday a sudden storm poured over Livorno in four hours the same amount of rain usually expected in three months. Six casualties. This is completely unseasonal - when people say you can't divine weather, they mean it.

Dressing questions in cooler months really depend on age. When I was much younger, I could be warm naked in the winter. Those days are gone.

Early mornings and late evenings can dip a bit chilly in late September. Sunny afternoons can still be quite warm. Venice can get windy, and those are winds off the Adriatic. Soft cotton layers and cashmere work best for me. I'm never without gloves and favorite sciarpe. I find rain coats too impractical. I have a fabulous German umbrella made for professional film photographers.

Early mornings and late evenings in October in Tuscany can get cold, like 48º. In recent years, Acqua Alta has arrived in Venice by mid-October. That's a beast that requires some preparation research.

I remember our first trip to Italy in late October. I traveled with a carryon and lightweight daypack.
For clothes I had black and tan microfiber pants. Every shirt/overshirt/vest had to go with both.
I brought the colors in with the tops so that it wasn't completely boring. I don't travel in or bring jeans,
they take a lot of space and a lot of time to dry. I find with long pants, in those two colors, I don't have to bring extra shoes to wear with skirts/dresses. It did rain some, mostly quick showers so I had a very lightweight rain coverup with rollout hood. Worked well and didn't take up much room.

Have a Great Trip and please do a trip report so we will know how it went and learn from it!

I'm packing today for my trip leaving September 13th - I like your plan and it does mirror my own. I like raincoats over umbrellas as they serve a layering purpose for those chilly mornings.

Thank you I'll be happy to trip report. We've been traveling with the kids in June and July. This will be the first fall trip since the 1980s--also the first us only trip since then.