I was a travel agent for many years, so I can PACK like crazy. I always roll, because it’s the most efficient use of space. Small items get poked into odd corners here and there, as well as into shoes. I’m not that worried about wrinkles, because I pretty much hang everything up right away and iron before I get dressed anyhow. I’m not much for roughing it, so I really don’t go anywhere I can’t use an iron. My idea of camping is no mint on my pillow! 
When my parents travel, she puts her shoes inside his, then puts socks inside her shoes. Oh, and if they fly and they have enough stuff for two suitcases, they put half of their clothes/shoes in each bag, so if one bag is lost, neither is without ALL their clothes.
Gah, the 3 oz. max liquids rule just chaps my ass, because it is nothing more than “security theater”. I NEVER checked a bag for any trip less than 10 days. Not anymore, alas. So the bare essentials go in carry-on – contact lens solution, face wash, face toner, moisturizers, deodorant, toothpaste, a few other things – and everything else goes in checked luggage, in Ziploc bags to ward off leakage.
I also always carry on my makeup, toothbrush, jewelry, and camera, plus at least one full change of clothes and several changes of undies/socks, a sleep shirt and/or robe, plus another pair of shoes, and my bathing suit if I’m going someplace where I might swim. I do this for two reasons. One, I think it sort of wards off Murphy’s Law and the travel gremlins, and two, if my entire wardrobe is gone, including shoes, I’m screwed. I’m a fat woman with big feet, and I can’t reliably find clothes or shoes that will fit just anywhere.