I have the same problem with DW, who has passed that gene on to DD (aged 5). We did a 4 day in October and my DS (age 3) and I each had 3 pairs of shoes -- "dress" shoes, sneakers and sandals. DW had 11 pairs of shoes (mostly sandals) and DD had 9 pairs.
Toiletries are the same -- she has her own carryon for hair stuff, makeup, curling iron, etc. etc. etc. I have comb, razor, shave cream, deodorant, toothbrush and toothpaste. All of her cosmetics must be carried on. Both plane rides. By me.
We spread things out among our checked bags so that if any single bag is lost or delayed, we could still survive. Life is much simpler now that both kids are potty trained.
We went to Target and bought a couple boxes of the largest Zip-loc bags that they had (2 gal. I think) and packed our clothes in them. You can squeeze the air out of the bags and pack more efficiently. Dirt from the soles of the shoes aren't a problem because the bags protect the clothes. You have to be careful, though, because you can get alot more in the bags and you could go over the airline weight limits.