Verdant hills, chilled chianti and endless people watching make the Italian Camino the Via Francigena a holiday to remember.

Diamond patches on backpacks allow wearers to lash their gear to the outside and are a holdover from outdoor-focused mountaineering backpacks.

Enter the bucket bag—a favorite of fashion insiders and A-listers like Taylor Swift, Selena Gomez, and Katie Holmes. Named for their bucket-like shape—think: deep interiors, tall sides—these bags come ...