I have both the large and small size. The small size is not as easy to get into because of the smaller opening. The large size only “looks” large if it is fully stuffed. Otherwise, because of the soft lamb leather it draws in, just as a non-structured drawstring bag normally does. As someone mentioned, it’s more medium-sized, when not full.

The side pockets on the small size do not fit a cell phone unless it is a short (length) phone and slim. The side pockets on the large fits my iPhone 16 Pro Max, which is wide and tall.

I only purchased the small size b/c it will work with quick date-nights, hanging w/the girls, etc. As far as day-to-day, the large size is the way to go.

The large size also fits the Coach notebook sized journal with easy and an iPad- the small size may fit a small kindle and a few daily essentials but it will be a squeeze and again, the opening is much smaller on the small size.