I do about a moderate amount of traveling - usually four times a year for work, for no more than a week at a time, and two or three times a year with Stephen or my family. This means that I am awesome at packing for short trips, and not so awesome at packing for longer ones (once, I went to Europe for two weeks and brought practically my whole house along with me. Then I used my hair dryer in the hotel and accidentally blew out the power. And I DID HAVE AN ADAPTER so I don't know what happened. Anyway).
This is how I normally roll.
1. Go carry on and don't look back
If you can, don't check a bag when you fly. It is HASSLES. And you know it's hassles because it involves waiting, separate lines, additional fees, stress if the bag is too heavy and all kinds of bullshit that you don't have time for. Also, I have THE FEAR that my luggage will get lost if it's out of my sight, or that someone will go through my stuff and steal my makeup (yes, I fear that the baggage handlers want my used makeup. I didn't say it was rational). Most airlines let you do one carry-on item and one personal article (like a purse), so that's my thing. For years, I used these babies:
They're easy to find, you can get decent ones that are very affordable (this one is $30 at Bentley's website) and they come in fun patterns and stuff. I like them, but once I bought my beloved Zuca bag, my brief affair with the 19" carry-on was over. Observe:
You like my sweet-ass luggage tag that Stephen made? Aw, yeah.
This thing is 10" wide, 20" tall and 14" deep. It's tiny and mighty and will last forever! If I can cram a week's worth of clothes and makeup and all the other shit I have in there, and still have room to bring back souvenirs, then you know anyone can. AND YOU CAN SIT ON THE TOP! Make everyone jealous while you sit on your luggage, waiting to board and everyone else is standing like a chump. Watch the video on the website, it will blow your mind.
In my purse, I usually keep the stuff that I need for the actual flight, like my Kindle and my iPod and snacks (bring snacks. Don't get hosed into that Buy-on-Board shit where they swindle you into a sandwich and some carrot sticks for TEN DAMN DOLLARS).
When I get on the plane, I throw my Zuca bag in the overhead bin, put my purse under the seat in front of me, get out my snacks and what the fuck. Easy-peasy!
2. If you're going to do carry-on only, you have to commit to solid products.
LUSH is your best friend for travel. We make EVERYTHING in solid form. Shampoo, conditioner, body butter, hand cream, cleanser, toner, face moisturizer - all of it. Solid and preservative-free. The only stuff that goes in my clear zip-top bag is sunblock, lip gloss and tiny containers of stuff like eye cream and foundation. For toner, I usually bring an empty toner spray bottle and a Token to the Forest Gods toner tab. Once I get there, I throw the tab into the bottle, add hot water and shake it up. Instant toner, good for up to two weeks!
3. Make a list of everything you're bringing.
I make a packing list every time I go anywhere. It keeps me from forgetting stuff, and helps me minimize (when I see it written down, I'm like, "Eh, do I really need to bring a blush, contour and highlight?"). Also, I bring the list with me and then use it to double-check that I have everything when I pack up to come home. I am a crazy person and I itemize it by category.
Yes. Your eyes are not deceiving you, I also write down exactly which bra and underwear I am going to wear on which day. Don't judge.
4. Give yourself prep time and recovery time.
If I can swing it, I usually take off the day before I travel, and at least one day after I travel. I need the day before to wash my makeup brushes and do laundry, and I need the day after to deal with jet lag. This doesn't always work out, but I do try. Nothing is worse than coming home, sleeping for two hours and then working a full day. Blech!
Aaaand those are my best travel tips. Hope that helps!