I see businesswomen all the time with purses+briefcases+roller bags, and have never seen an issue.

My mother, for example, has always flown with, and still today flies with the 3-- a 22" Tumi roller, a slim briefcase, and a normal sized purse. Never had a problem on Air Canada, United, US Airways, or Westjet. I've been with her where she takes the above mentioned luggage, plus a shoe box with full sized boots on a plane (That box was about 22"x5"x15"). She didn't even get a second look (Granted it was an express flight, she lost the roller at the door).

I think for the most part, if women make it look like a purse and a briefcase, there is no problem. I think the issue is some women bring two massive tote bags claiming one is a purse, and then stick them both is overheads, along with their full size roller suitcases. This annoys people, and with good reason. Any real businesswoman would keep her purse by her feet, and her briefcase right there as well--and with carry ons, thats no big deal. The problem is when bins fill.

Also, having a shiny elite tag on your bag never hurts