As others have already mentioned, I'm a big fan of Eagle Creek packing cubes. I use one of the zippered pouches for my toiletries. It's soft-sided and the pouch will efficiently fill in the nooks and crannies of the bottom of the bag. I have a set of travel sized containers for toiletries that I refill as needed. I double bag everything in case of leaks, or if TSA pre-check lane isn't open and I need to pull these out. I.e., I put the liquids in a clear ziplock bag, then in the Eagle creek pouch.
I count out vitamins & medicines and put them into a daily pill box. I duplicated make up and comb and brush and other items, so my toiletry bag is always packed and ready to go. The brush I bring is bulky -- I put it together with my flat iron and wrap a Turbie Towel around it to protect both, then put it into an Eagle Creek sleeve.
I have a set of silk pajamas & robe specifically for traveling, because silk takes up very little room in my luggage and is just right for hot OR cold weather. Silk camisole and leggings are very useful for layering for warmth. And silk washes and dries quickly. What's more, I pack my jewelry in the same travel pouch with the silk items to protect the jewelry.
For longer trips, I bring synthetic underwear which can be washed out in the sink and dried over night.
I start my packing strategy with shoes, aiming for no more than 3 pairs, one on my feet and two in the bag. Exception is that I can easily fit an extra pair of thong sandals into the bag since they don't take up much room. I have found that black shoes tend to work best and provide the most versatility, but sometimes I can manage a travel capsule that revolves around more interesting shoes, like on my last couple of trips, I planned around a pair of turquoise suede loafers.
I never take more than 1 pair of jeans, because jeans are bulky. (And no, I do not like to wear them on the plane). I usually bring a pair of black pants as well, and one more pair of pants OR a dress. (Although there have been some trips where all I packed were dresses). Then I choose tops and accessories. I do find a neutral black, white & 3rd color palette goes far. I always bring at least one extra top just in case. I usually bring at least two scarves, one that I wear on the plane and one packed in the bag. I usually have room for 2-3 toppers. I wear the bulkiest one on the plane, put one in the luggage, and one in my laptop bag.
I always bring a reuseable shopping bag that rolls up small (works as a beach tote), and I like simple flat clutches because they pack well.
I lay things out virtually on a powerpoint first, and to keep a record for future trips. I then lay things out on the bed before packing to ensure I have everything I need (including the right bra & underwear for an outfit), and will often do a try-on before packing it all.
Items get packed in a specific order:
1) Belts line the interior of the bag
2) The two shoe bags and flatiron/hairbrush go on the bottom between the handles
3) Toiletry bag next, filling in the nooks and crannies
On the next layer:
4) Small pouch with silk items & jewelry next
5) Small compressible pouch with underwear
6) Medium compressible pouch with rolled tees and knits
7) Eagle creek folder goes on top of it all; I fold items like this -- blouses / tops on bottom, then a topper, then pants, then jeans, and finally, a scarf
Then I have a laptop bag that fits over the handles. In it, I pack another topper and scarf (in it's own pouch to keep it clean), laptop, electronic chargers and headphones (I have an extra set that is kept packed), book to read, and a small handbag / extra clutch. I can get a lot in this one bag, so if needed, I can fit another eagle creek pouch that has swimsuit, cover up, hat for the beach.
I can pack quite a bit in my carry-on plus the laptop bag. I've not checked a bag in a long time.
