Last year prior to my first trip to Paris, I obsessed for months about what to wear and pack. Between mon mari, who is a chronic over-packer, and my own desire to have whatever just-in-case items available for this most stylish of destinations, we ended up shlepping an oversized duffel and another wheeled bag both of which we checked, in addition to a wheeled carry-on bag. I wore probably half of what I'd packed, and getting all of that luggage through customs (especially on the way home where we were trying to make--and ultimately missed--a connecting flight), made me vow that a) I'd pack much lighter next time and b) we'd invest in some luggage that was better designed.
For a start, being able to survive for two weeks with nothing but a pair of trousers, two tops, one dress, a pair of flip-flops, a receptacle to purify your urine and a spool of twine (or whatever) all squashed into a handbag is nothing to boast about.
...And moreover, would you wear the same shirt (or anything else) four times in a week at home? Of course you wouldn't. So why, in the name of all that is fragrant and sanitary, would you do so on holiday?
The development of my own packing modus operandi owes a great deal to the fear of having to wear dirty clothes. So I've erred in the past on the side of too much rather than too little. But the last two trips I've taken have helped me figure out which items are the essentials and which should be left at home. Strategies I've developed from my recent sojourns (and these apply mostly to visiting a single locale/climate per trip):
1. Pick one neutral for basics (pants, jackets, shoes, bag) and work around it. No surprise here, but black is my choice for all but tropical destinations.
2. Bring multiples of black and white t-shirts that are light enough to be used as layering pieces. (Banana Republic makes an excellent one.) A black t-shirt under a jacket can also look dressy enough for most venues with some jewelry or a scarf.
3. Bring scarves to accent and change the look of your neutral ensembles. (But you knew I was going to say that, didn't you?)
4. Bring 2-3 bags maximum - one for day, a small one for evening, and (optional) a bigger, lighter bag to be used for a personal carry-on item (for airlines that allow in addition to a carry-on bag).
5. Carry cell phone and laptop chargers with you. Lost luggage + dead cell phone = Extremely Grumpy Traveler.
6. If you've followed #1, you should be able to get by with two or three pair of shoes (wear one, pack 2).
7. Rolling some clothes, packing clothes individually in dry cleaning bags, and underpacking will all help prevent wrinkling. I do usually pack a small travel steamer, just in case.
8. Bring a Tide spot removal pen, and some powdered handwashing soap to wash items in the sink. Bring a small sprayer full of Febreeze to get smoke or other scents out of otherwise clean-enough-to-wear-again clothes.
9. Bring no more than 1-2 pairs of denim jeans. They are bulky, heavy and you can usually get 3 wearings out from a single pair before they need washing.
For any trip longer than 2-3 days, I use a bag big enough that it has to be checked. Some airlines are starting to charge for checked bags. I know for some travellers it's a matter of pride to be able to get two weeks' worth of stuff in a carry-on bag, but I reside somewhere between that extreme and Hadley Freeman, whom I'm guessing travels with a team of sherpas.
What are your packing philosophies and tips?