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Love all these great packing tips! I am what the kids today call an "EMO" dresser, meaning I like to be able to dress according to mood (at least to a small degree) as well as climate and activity. So if it's a city getaway, I'm likely to bring too much, just in case I have an unexpected sartorial "feel." On the other hand, I've managed to pack in a 7kg duffle for a trip to Singapore and a similarly-sized duffel for two weeks in Africa, so when the chips are down I can do it! I agree that it is no fun to feel weighed down by one's stuff, literally or psychologically, when on vacay.
Since I need options (unlike the admirable Genie, there is no way I could plan every outfit in advance), I try to pack so pretty much every item can be paired with pretty much any other item, and in layers, to allow me to "build" my OOTD. But I do bring a selection of good jewelry, because frankly my at-home lifestyle doesn't allow me to wear it much, so by golly Ima gonna swan about a bit on holiday! :p
I used to pack a lot of clothes as well as shoes. And always ended up with pieces unworn but having the options made me feel assured! Am I the only one who finds shoes take so much space! I hate bringing them! I used to bring PJs for long haul business class too. But now I change into yoga pants and hoodies on the plane.
 
The jacket selection can be problematic. These days I feel I have to make that decision the day before I leave. For example I went to Roland Garros this year. Before the trip, I assumed unpredictable weather, but definitely cold (for me, anything below 80 is cold) and possibly rainy. I purchased a black jacket (functional justification) ideal for what I thought would be the most likely weather scenario. Two days before I left, I looked at the weather and major heat wave in Paris. I had to rethink everything and ditch the jacket I planned to wear (which I still havent had a chance to wear yet). Not that I am complaining, I was very lucky in that it only rained during one match and they were back on the court within the hour. It could have easily rained the entire time i was there!

On the subject of bags, I just remembered that on one trip, I used a King Power Duty Free carrier bag as my day bag. It was awesome, it snapped shut at the top, was plastic and therefore water proof, and quite sturdy.
 
I always save my samples for travel I even transfer hair gel to a tiny bottle. I usually take too much makeup and this time have been more intelligent about by remembering past things I did not use. I have already gone to a smaller makeup bag.

So true about weather and clothes. Sometimes you hit it right and sometimes not
 
I find I have to bring all kinds of shoes. And XX is right -- sometimes I think it takes up half of the suitcase.

Yoga pants or leggings for long haul trips, even when I am in business class (if I am lucky but a must for trips to Asia).
Funny, the one place I don't have a big problem is which shoes to take, however, I am now second guessing myself regarding the possibility of swollen feet with the elevated humidity. The last thing I want is a big fat blister!
 
Funny, the one place I don't have a big problem is which shoes to take, however, I am now second guessing myself regarding the possibility of swollen feet with the elevated humidity. The last thing I want is a big fat blister!

Easy space saving solution: pack a box of special blister bandaids regardless. They've been life savers for me.
 
@lulilu, I've tried those sticks but they don't work for me. Obviously you don't want to have a blister in the first place, but these really are great for protection and healing as well. (No, I don't work for Band-Aid Brand! LOL!)
 
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