I'm not sure why traveling throws such a wrench in how I dress myself, but it does. I like to wear cozy stuff for the plane, be able to pack work- and weather-appropriate stuff and also have shoes that are comfortable enough to walk around in for longer distances in case we have a "that vegan restaurant is farther away than we thought" kind of field trip. Add in the weather variables of both the heavily air-conditioned meeting space and, well, any other climate, and it's a challenge for me to pack efficiently.
Thankfully I tend to wear something to death if I like it so I managed to wear the same necklace, jacket and shoes (mostly) for my last work trip. (I wore some fake vegan silver Birks in off hours sometimes.) When packing, I like to lay out what I can wear together day by day (so I don't forget to pack something, like, oh, pants when I have all shirts). But when you have so many dupes that you'll wear most days, you can't just lay them out flat as an outfit to make sure you didn't forget anything so I take photos of each day's clothes grouped together. Also, I never remember what I planned to wear on which day by the time I get to the destination and this makes it a brain cell-free endeavor.
Packing for personal trips is slightly better as I don't mind re-wearing the crap out of most things as long as the weather is decent.
^ the 3-day trip layout ^
top left - leggings & babydoll dress on plane
top right - first day of meetings
bottom left - first day of conference plus a change of logo gear
bottom middle - last day of conference and travel home w/leggings
bottom right - contingency dress
^ I thought I could swing a hotel outfit photo but... ^
the lighting was way too dark
I also have a standard packing list in my iphone Notes and copy it over to a new Note to customize it (legwarmers, bathing suits, sunhats, gloves, thermals, rice heat packs because I'm a baby in cold airbnbs) for each trip. Then I go through it, deleting what I've already packed. I think that's pretty standard -- we all have that, right? Before I started doing that, I would forget to pack contact solution (very bad) and pajamas...while I was staying at people's houses (very very bad).
I also roll my clothes for packing but not individually! Sorry Marie Kondo! I lay them out on top of each other and put the most wrinkle resistant thing at the "inside" and then roll the whole thing up like a burrito. I think this keeps most of my stuff wrinkle-free since it's not too sharply creased anywhere. Also, it takes like half a minute to do.
Oh, and my liquids and personal care items always always come with me in my carry-on. I am not getting stuck without moisturizer, contact solution, glasses or deodorant, ever.
I'm not sure how this ended up being a packing tips post - all I really wanted to share was the outfit-photograph-a-day thing, since I found it helpful, but found myself getting really self-righteous about my packing practices the more I thought about it. This is really more of a response to correcting the billion packing mistakes I've made prior than being an actual expert on packing -- but you got yet another packing advice blog post anyway!