Cute bag but nothing special. I bought an insert to help with organization but it really helped hold its form and sit straight. The main shoulder strap is the only thing on the bag that feels "nice". I'd even consider buying another strap to swap out to change it up in the future.I'm not sure how some carry a laptop or even an iPad in their MEDIUM tote. doesn't seem like it would fit. I'm not even sure my calendar is going to make the cut and I'm super bummed about it.Edited to add that the calendar does fit but just barely. Your iPad will fit but it's going to cut it very close. Now I'm wondering how the large compares.