I debated between the large and small. The small is the ‘medium’ on most other retailer sites. So it is still a ‘tote’, and can fit an iPad, wallet, makeup purse, and hats/ gloves, etc. Being petite and 5’2 I went with the small and it’s perfect for my needs: an everyday purse. I’ve had many friends comment on the size being perfect and what they’ve been looking for as many totes are simply too big for everyday activities. If you would like a true carry on size/ school bag / diaper bag then go with the large. If you’d like an everyday oversized purse (and I still am able to carry snacks and two water bottles, in addition to the above items mentioned, for my very young children) then you’d be happy with the small. The gunmetal threw me for a loop a bit because it is not as obviously gray like in the photo. It can pass as black with many outfits. I debated exchanging it for the khaki, but decided to keep it thinking would be slightly more timeless.