Bags and Baggage

Apparently in recognition of the fact that one really can’t travel internationally on the contents of a carry on (even though some of the “carry on” luggage I’ve seen looked like wheeled steamer trunks) most of the airlines don’t charge for the first checked bag internationally, although I believe there is a 45 lb weight limit.
I have – since the luggage meltdown in NY – purchased a small rolling suitcase made by Lucas which behaved admirably on its first outing on a business trip to Philadelphia. It came with a matching sort of purse and I was fortunate enough to find a small wheeled carryon from the same line on sale on eBay. I think those three items should be sufficient.
I’m trying to construct a packing list that will allow me to dress for comfort, warmth and reasonable neatness so that I do not cut the brutta figura that most Americans seem to do overseas in badly fitted khakis, tight jeans or shorts with t-shirts and fanny packs. One lesson that was brought home to me in England in 1995 was that dressing unlike the tourist hordes meant getting treated, in general, more like a traveler than a tourist. Now I am a tourist, I see no shame in the phrase, but all of my early indoctrination as a military dependent not to offend one’s host country makes me want to be taken as a respectful traveler. What didn’t matter in my teens and 20s matters a bit more now that I’m in my creaky mid-50s.
The clever little rolling carryon arrived today and includes a document case, a pair of slippers for the filthy floors at the TSA checkin, and a hanger bag for toiletries. Very nice and it looks as though I can strap it on top of the larger Lucas rollie once I collect it at the end of the flight.
Now to start constructing a packing list and see if it all fits. I'm thinking wool trousers (average high in February is 55F) light sweaters and turtlenecks for layering, one good plain sweater for outwear and my good coat (which will be a wear on, not a packable), plus one calf length skirt and one dress. I figure the bottoms are good for 3 wearings assuming I don't spill anything on myself - it's tops that will be the issue - pack enough, hopefully to only need two wearings? That would mean 5 shirts or sweaters. Plus underwear and shoes. Probably 2 pair of shoes above and beyond the pair I wear on the plane - two pair of walking shoes and one pair of nice flats. Heels, me and the cobblestones of Rome? Not something I'm willing to chance.
As for the rest, I'll buy things like soap and toothpaste and shampoo there, just bring the minimum of cosmetics and then my various allergy and fibromyalgia medications.
Hopefully that will leave room and poundage for the 3 guidebooks I plan to bring, one Italian-English dictionary, the wee Dell netbook, power supply and a converter. Only one of the guidebooks is bigger than a very slim paperback, the other two are quite small and one has a pocket with an excellent map. My little Nikon Coolpix, its sync cord and some extra memory cards. I particularly want to bring the computer because it will allow me to download the camera and to stay in touch with family via email, as well as ease of making museum or train reservations online vs on the phone. I also plan to download a few e-books from the public library onto it, so that I'll have my nightly reading material without lugging books or buying expensive English language books there.