Cloud Carry-On Bag

I have this Baggu bag in black and it's perfect. Great size with a squared flat bottom, two outside pockets, and it fits over rolling luggage with their trolley sleeve. Super lightweight so you can roll it up as an extra bag in case you plan on bringing things home from your trip. The detachable pouch doubles as a clutch, which is nice. Comes in lots of colors. I really love this stripe one from Ruby Press.

photo from Ruby Press