Travel well by packing two bags, not five.
For the journey
A roomy tote or weekender with a zip top keeps passport, headphones, a layer and a water bottle within reach. Slide it over the handle of your carry-on and your hands stay free.
For arrival
Fold a compact crossbody or clutch inside the larger bag. Once you land, it becomes your city bag for dinners and evenings without unpacking everything.
Colour strategy
Choose one dark and one light piece — black and cream, or cognac and ivory — so either works with everything else in the suitcase.