Oh, I hate traveling. I really hate it. Partly because I have insomnia :(
Anyway, you do sometimes have to travel. Either it's bussiness, or simply because someone pay for your trip :D
Here's what I bring when I'm traveling:
SMALL CROSS-BODY BAG
Mine is Elizabeth (made in Indonesia). This is where I keep my ticket/passport, important medication (paracetamol and Diatabs, hehehe), lipbalm, pocket tissue, wallet, cell phone, ballpoint, hand sanitizer (in mini size) and small folding hair comb.
MEDIUM SIZE BACKPACK.
Traveling isn't time for cute backpacks, so I bring my green Delsey. It's where I put anything that can't be stored in my luggage or something I want to use later in flight. I put my sweater coat (I'm a hot person. I mean, I can't stand the cold), personal medication (won't put them in baggage), a hat (something to keep my head warm during flight), cell phone charger and 1 pair of clean underwear.
I always afraid that the luggage would lost somewhere, or something bad happen such as bad weather and stranded in airport for hours with low battery and dirty underwear :D
Always travel with wheels! Carrying regular travel bags would be exhausting.