I must admit that I was not always such a light packer. My family can attest to my over packing tendencies in the past. My flight attendant days definitely taught me a new way to travel. I feel like packing is a science and I have spent tons of $$$ trying new bags, inserts, cosmetic cases, etc. My intent is to save you some $$$ and help you take the plunge to try carry on bags only for any length of trip. I have found it is so much easier and enjoyable to have fewer choices and cart less stuff around. Plus if you need anything you can always buy it.
Of course weather is determining factor so we are going to have two lists- one for cold weather and one for warm.
For a warm weather trip of any duration this is what I pack:
Flip Flops, flat black sandals, another pair of black flats and I wear comfy shoes that I can walk all day in, like loafers.
I wear stretchy black pants that look like jeans (NYDJ) that I get at Nordstrom. They can be dressed up or down. I wear my heaviest shoes that I am taking and I wear a tee shirt and wear a cardigan sweater over it all.
I have my two Flight 001 Space Pak underwear bags and all my clothes are divided into them. I pack skinny jeans, yoga pants, 2-3 stretchy dresses, skirt, bathing suit, underwear (only 3 pair), shorts, 2 tee shirts in black and 2 white tees. If I am going on a cruise I add a long dress that is stretchy. (I never do the fancy, dress up nights.) I also take a black button up sweater that goes with everything. I throw in a scarf or two to add some color.
I also pack a sun shirt (REI has great ones). I wear this as a bathing suit cover and also for coverage going to visit churches.
Everything can be mixed and matched and I do end up wearing the same combos a lot but I am usually not in the same place twice.
For Cold Weather- I take pretty much the same, but instead of sandals I wear boots and skinny jeans and pack loafers and another pair of black shoes. I add a Northface down jacket that squishes into the front pocket of my carry on bag. I wear a blazer or jacket that I can wear with the black pants or jeans