Sasha Pleated Hobo Crossbody

One that closes at the top and goes across your body, so your hands stay free and nothing can be lifted out of it while you are looking at something else. The closure matters more than people expect on a day like that, because an open-top or snap-top bag spends hours facing outward in a crowd. Look for roomy enough that you are not digging, but not so large that you fill it and end up carrying the weight all afternoon. This one zips all the way shut across the top and wears crossbody, with a back zip pocket for the few things you want to reach without stopping.

Stand it upright on a shelf with a little soft stuffing inside, tissue paper or a spare scarf, and do not hang it by the strap. Hanging stretches the strap and slowly pulls the top of the bag out of line, which is the damage people notice a year later and cannot explain. Keep it out of direct sun and leave it some room rather than wedging it between other bags. A soft, pleated hobo like this one wants less stuffing than a structured bag, just enough to hold the shape, because packing it out round is what flattens the pleats.

A short shoulder strap with a 13-inch drop and a longer adjustable one that runs 18 to 29 inches, and you swap them yourself. The brass rings on the bag open up, so you unhook one strap and hook the other one on without any tools. At 13 inches the bag tucks up under your arm, which is the dressier way to wear it; let the long strap out toward 29 inches and it hangs at your hip and stays out of your way. The bag is 9.5 inches tall, 12.5 wide and only 3.5 deep, so even at its widest it stays flat against you rather than sticking out.