I’ve seen a couple of those in the street myself; they seem cute, and I’d be tempted to buy one except that they don’t seem heavy/supportive enough for me. (I tend toward medium-sized leather bags with a longer strap so that I can tote along a small umbrella/book/assorted crapola.)
My theory about the pit bags is that they’re actually meant to be carried in the hand or in the crook of the elbow, as are the chintzy little evening bags you’d carry for a night out on the town. But once women realize how inconvenient that is for long distances/tempting to theives, they resort to tucking it up in the pit…