I often use a Burberry nylon tote as a carry-on and for rainy and carry-a-ton days, and then pack one or two premier crossbody bags to use on good weather days when I don't have to carry a lot.
For fall/winter, I usually pack a Proenza Schouler PS13 crossbody bag in black or a Tom Ford Alix shoulder bag in wine. Spring/summer options include a Celine trio in light yellow, a Maison Martin Margiela bag in blue and white snake print, and a Mark Cross mini Madison in burnt orange. My
Gucci 1973 black chain crossbody is a great day-to-night option.
Having one or two bags I love with me makes me enjoy my trip a little more

.