I found this thread to be so entertaining and right on! I am exclusively a shoulder bag wearer. I wear my bags slung toward the back and both arms are free. I am carefree even when I wear an occasional suit although I prefer t shirt and cardigan with skirt and good ole jeans! Lately, I am viewing and purchasing a more tailored style hobo rather than my usual hobo bags where I throw everything in, Other than that, while Iove the look of a finely coiffed woman wearing a handheld on the crook of the arm, I've come to the conclusion it is not for me.