I was recently exploring the Massai Cut, as well...hoping to add a true shoulder bag to my collection. The 40cm works better for me...but I have a bit of trouble with the pricepoint given that it's lined in toile...much prefer leather lining in spite of the added weight. S'mom, have you considered the 37cm Paris Bombay (High)? It holds so much, is lined in VN and fits over the shoulder nicely.