This is what I usually carry and they fit easily in the Calista:
Medium or large wallet
Checkbook
Small cosmetic case
Maui Jim sunglasses in Maui Jim case
Reading glasses in case(sometimes)
Rolled up reusable shopping bag
Business card case
Two phones-personal and work
Work keys on a long chain key ring
Personal keys
Clipa purse ring
Other miscellaneous small items-eye drops, mints, pen, and a small pill case
Medium or large wallet
Checkbook
Small cosmetic case
Maui Jim sunglasses in Maui Jim case
Reading glasses in case(sometimes)
Rolled up reusable shopping bag
Business card case
Two phones-personal and work
Work keys on a long chain key ring
Personal keys
Clipa purse ring
Other miscellaneous small items-eye drops, mints, pen, and a small pill case