My trip to Rome is less than two weeks away and I'm a bit stumped what to pack. I'm going for seven days with just a carryon (my Osprey). I plan to take my Tom Bihn Daylight backpack for everyday, it will pack down to nothing in the big bag during the flight.

Normally I start my planning with shoes and outerwear, but I'm really unsure about temperatures and weather. It usually shouldn't rain that much, but years ago on a similar trip in February they had rain non-stop. I don't want to wear a rain jacket, I usually prefer my umbrella for just in case. Right now temperatures are predicted anywhere between 3ºC in the night and 19ºC during the day, with both rain and sun. Last year I took only my black boots and wool peacoat and it worked out well, but we were much farther north (highest temperature 12ºC).

I could take my Trippen boots which are lower than the black boots and don't need to be worn with thick socks. But I haven't really worn them for long stretches of time so far. Or I could take my rather dainty old black oxfords (probably fine for the temperatures but not good in the rain) and add my sneakers for rainy days. But then I'd need a new pair of jeans I could take, I hate wearing mine which are all worn out or too big in the waist. I could also just take the black boots which are super comfortable and wear them with socks on colder and rainy days and try if I can add the insoles of the Trippen boots to them to make them work with thin socks too.

I thought taking the wool coat which I can leave unbuttoned when it's warm, without a big scarf or anything. It might be too warm at times, but it is breathable and would probably transition best...

My clothing rather depends on my shoes and I would need to do some very targeted shopping (tights, jeans) soon, depending on what I'm going to take. It wouldn't be necessary at home, but with a small travel capsule...

What do you think? Any and all comments are appreciated.