Stackable does not always mean easy to reach
The bottom box should still be worth using after everything else has been placed above it.

Count the lifts
Imagine retrieving the item you use most often. If it lives in the bottom box, how many other containers must move first? A tall stack can use vertical space efficiently while making daily access tedious. Put frequently used contents near the top or choose a system with suitable front access.
Stackable means something specific to the product's design. Check whether lids are required, which sizes are compatible and what load limits apply. A flat-looking top is not enough evidence. Do not create a mixed tower of unrelated boxes simply because their footprints are similar.
Keep the weight predictable
Place heavy contents where you can lift them safely and follow the storage system's instructions. A light-looking box can become a substantial load when filled with papers or tools. Avoid lifting a stack as one unit unless the design explicitly permits that handling.
Think about the surface below. A soft carpet, uneven shelf or narrow support can change stability. Do not solve a wobble by pushing the stack into a wall and assuming it will stay there. Use suitable furniture, observe its load and anchoring requirements, and keep the arrangement stable.
Label the accessible face
Labels on lids disappear once boxes are stacked. Put identification on the front you will see, and make it specific enough to choose the right box. Spare cables and winter accessories are more useful descriptions than storage one and storage two.
If containers need to be moved frequently, handles should remain accessible. A close-fitting shelf can hide the grip behind an adjacent box. Leave room for your fingers and for the movement required to remove a lid without levering it against another container.
Keep stacks short where access is frequent
Two accessible stacks may work better than one tall one, even if the footprint is larger. Alternatively, separate the daily collection from long-term storage. The occasional box can sit farther back without slowing every routine task.
Before buying a large set, fill a small number and use them normally. Notice whether lids flex, labels disappear or the lower boxes remain unopened because retrieval is awkward. Those are reasons to change the arrangement, not to add another layer. Storage should reduce the work of finding things, rather than hide that work in a taller pile.