Smart gesturing may facilitate smart shopping and other contactless experiences by enabling a user to perform a natural gesture toward one or more desired items with or while wearing a wearable or non-wearable electronic device. The electronic device may identify the smart gesture, and determine the one or more desired items are indicated by the smart gesture. The electronic device may identify the desired items by receiving location data of multiple items, determining a vector based on a first position a second position of the smart gesture, extending the vector to a location, and using the location data to determine which item or items correspond to the location. If more than one item is indicated by the smart gesture, the electronic device may enable selection of the items and, if at least one item is selected, provide information on the selected items or enable additional interaction with the selected items.