This morning, before the start of the last day of this weeklong workshop I've been attending this week, the people at my table were talking about their luggage packing practices. One woman was planning to go on a cruise that apparently stopped on at least one island; she talked about bringing five swimsuits, extra shoes (and by that she meant heels), plus more formal wear for evening activities. She was really stressing out.
I was relieved that Ed and I have enough practice traveling that packing has become a non-issue. We don't bring formal clothing because we choose to forgo more formal activities (for my part, I simply don't like getting dressed up - not my thing); formal clothing takes up a lot of space for minimal use; t-shirts and jeans we would wear many times throughout a trip, while formal clothing we might wear for part of one day. Plus, you know, we haven't traveled anywhere yet that doesn't have laundromats somewhere.
In terms of shoes, whatever we have on our feet is what we bring, most often just sneakers or boots, which are good for walking over uneven terrains, through grass and fields, that won't lead to soggy feat if it rains a lot. (On occasion I've been known to bring flat sandals - something akin to Tevas - that can be placed against the sides of luggage.)
Ed and I pack and bring carry-on luggage; if it doesn't fit, it doesn't come. We also tend to pack fairly quickly, and don't find packing especially stressful (probably the result of having done enough traveling to know what we need). How or why people feel the need to pack multiple bags with multiple pairs of shoes - unless you're moving or traveling for months at a time. Most of our packing mentality is the result of nearly always flying standby. If we check our luggage, there can be a good chance that our luggage will travel interesting places without us. (Plus we don't have to wait for our luggage at baggage claim.)
I think people make travel harder on themselves than it needs to be. There are certainly stressful aspects of travel, and one can't control everything, but packing does not need to be the difficult part.