The way I resist is that I handle my own stuff. Even at 70, if I can't manage it on my own, I shouldn't be traveling. My next trip will be solo, 6-weeks in the UK. I pack for a week and a day and do laundry in the sink, by myself in a self-serve laundry (lavanderia in Italian) or have it done for me. For our 4+ week trips, I cannot possibly carry enough to not have to do laundry. I don't have enough clothes to do that, even for for 2 weeks.
For me, taking a break to take care of laundry is not a big deal. I certainly prefer that local experience to taking so much stuff I can't carry it on. See those people with backpacks or roller bags on the street? They are not all people on a trip. Some are Europeans dealing with their laundry.
About the shoes. The person who said to take a look at the Walking Company was absolutely right. I've tried just about every brand of shoes you'll find mentioned in the Best Walking Shoes for Travel forum section. For casual shoes, my first choice after all the experimentation is Abeos. I'm taking these to the UK. They are light weight and perfect for me. You may find other brands or styles better for you. I could never wear sneakers because they typically are not supportive enough and the soles are too slippery in wet weather.
My "go anywhere, over cobbles and rough terrain, paved or not, in the wet, super supportive, I can wear them all day and my feet, legs, knees and back don't hurt" boots are these Ahnu lace-ups. I'm taking a pair of gray ones to the UK. You're probably rolling your eyes and wondering how anyone could wear those ugly shoes. One reason is that I never wear skirts, not at home and not on trips, so the tops are always covered up. One reason is that they actually make my feet look smaller. One reason is that they are water resistant. That came in handy when it poured and hailed in Italy the last time we were there -- the first week of November, 2014. I did wait to go out until the water receded a bit, but I still had to go through some fairly deep puddles at some corners. As someone else mentioned, sneakers would be soaked in that kind of weather.
About the clothes. I grew up in San Antonio. I live in Tucson. In-between, I've lived in OH, OR, WA and Germany. I much prefer just throwing a jacket or sweater over my normal hot-weather clothes. I hate layering, but it is absolutely the smartest thing for cold, wet and windy weather. Amazingly, I used the least clothes on a trip to the Netherlands and Belgium in April. It was mostly cold and windy with a little rain. I looked like an idiot getting on the plane in Tucson (and Atlanta) with my multi-layers and button-out lining trench coat. I felt like a genius when we arrived in Amsterdam to sideways wind and cold rain.
I did read a funny story here on the forum years ago. It was about a person like me who obsessed over what to take, how much, how to coordinate, etc. When she looked at her pictures from the trip, she realized that she looked the same in almost every one. Why? She always had the same coat on with no change in scarves or accessories that would show. Did it affect her trip? Only after the fact and only if she was more concerned about how she looked than what she saw and experienced. That was a good lesson for me.