When I first started teaching watercolor workshops in Italy, I tried to pack everything into a 21" carry-on bag plus one tote bag that fit under the seat in front of me. I searched the internet for any advice on how to look good while wearing only combinations of sink washed clothing. It wasn't pretty when the pictures came back from my first trip. My easy to wash cargo pants looked tacky and gues what? Like they had been washed in a hotel sink. Imagine that!
So I studied other women at the airport and some of my students who looked pleasant while traveling. The first thing I learned was that you could bring a huge purse to fit under the seat in front of you. Also I went out and bought a rolling tote that fits into the overhead and carries everything I need if my luggage gets delayed or lost. It was delayed 24hrs. on this last trip and I wasn't stressed. The huge purse fits on top of the rolling tote and rolls thru the airport easily so you don't have to schlep your tote and purse and get an aching back before your trip even starts. I also learned from Eileen Condon, experienced world traveler, to pack my clothing in huge zip lock bags that I bought at Target and squeeze the air out. That alone lets me bring 50% more clothing! Lastly, I bring an x-large folding bag that fits into the bottom of my suitcase. I open this up toward the end of my trip to bring home all my wonderful treasures I found during the trip if my suitcase is too full. Sometimes I bring home some extra pounds too especially when I have eaten delicious food in Italy and France, but fortunately the airlines don't weigh me too.