1) Are you planning to use it for work, play, special occasions, all of the above?
2) Do you like shoulder carry totes, hand carry satchels, or cross-body bags?
3) Do you like embellishments like chains on the straps, hardware, locks?
4) Do you like to carry larger or smaller bags?
5) What are your favorite colors?
6) What is your preference between pebbled leather, calfskin leather, saffiano leather?
Take a look at the Hamilton, Sutton, and Selma in the luggage color that you like. They are all hand carried satchels with attached shoulder straps. The Hamilton has the most embellishments (chain on shoulder strap, hardware on belt, and lock) and comes in north/south (larger size) or east/west (smaller size). The Sutton and the Selma both come in medium and large sizes. Out of the three, the Sutton is the lightest when empty because it is made of a slightly thinner leather than the other two. You can view all of them on the MK website and then narrow down based on your preferences.