2. Coach Court Bag
Price: $258.00 at coach.com
This is my own favorite classic Coach handbag, with its top handle and removable, adjustable shoulder strap. I have it in black, though right now it’s only available in Mahogany. I like to wear it cross-body, but the carrying possibilities are endless… I’ve even used it as a clutch! It’s a little smaller than the City bag, but it’s still big enough to carry my A4 sized day planner and checkbook.