Jenn - I understand wanting some variety when you'll be attending a wedding and other events, but I would pack light shoes for the wedding and shower...something strappy but comfy and LIGHT in your bag. Wear sneakers for your airport and travel days and other long walking days, and then maybe another good walking (but nicer) shoe. I found some nice mary jane black flats that were obviously much nicer than an athletic shoe but with a good sole and support for more walking. They came in handy for nights out in Ireland, and I plan to bring them with me to Austria for things like attending Mass and possibly the opera.
A dress for the wedding, of course, but possibly a skirt/top combo for the shower than can be recycled on another day, either together or as parts of another outfit? The key for me is accessorizing. Even if the dress and skirt are more casual materials to prevent wrinkles, you can throw on a big statement necklace, or buy a scarf in Italy as both an accessory for the wedding AND a souvenir for yourself.
And you don't have to spend a lot of time doing laundry. On my 10 day trip to Ireland we did laundry only once. We had finally landed in a town where we were staying two days and I just grabbed my items and my friends items. It was only one load, and I made my way to a laundromat where an older woman was working, with a heavy Irish accent that I could barely understand, and she just took my coins and put on all the correct settings for me. I got to sit with my guidebook and a coffee and take an hour to relax. That's the cheap way. Many hotels you can send out your laundry, but I liked mixing with other people. (Part of that "Europe through the back door" philosophy.)
Finally, consider packing an empty, light, backpack or tote bag in your suitcase. That's what I did for my first trip. I knew I wanted to carry on my suitcase, but checking it would have been free for an international flight (check with your carrier). My intention was that way on my way home I could have checked the suitcase and carried on the backpack (RS Civita daypack - now full with souvenirs) and my purse. As it was, I just rearranged things and fit more in my suitcase and carried home the backpack - with my purse in it, plus other items. This time I'm not even bringing that empty backpack. I just got a larger purse and plan to pack even lighter so there's room to bring home a few extra things.
Whew, ok, that was a lot, but I'm passionate about this because I am a chronic over-packer (especially for road trips) but I did SO WELL on my first trip abroad. I never would have guessed I could stick to one small convertible suitcase and one small personal bag, but it can be done! Also, souvenirs can be small...they don't have to take up that much space!