Charisma trumps looks any time, in my experience. People who are average looking but have great personalities and great self-confidence often do better in life than attractive people with no personality or confidence. It's amazing how much charisma can accomplish. Case in point is a woman I knew in college. She was far from attractive. Her nose was very prominent, she had a lazy eye, her breasts were so large that they sagged like a 50 year old's (she was 19), she had broad mannish shoulders, she was overweight, and she dyed her hair a very unnatrual shade of blonde that did not flatter her skin tone. Yet this woman had dozens of men wrapped around her little finger. At any given time she was dating at least 3 different guys, all whom were older (usually grad students) and were generally very good-looking. She could walk into a party or even the campus coffeeshop, strike up a few conversations, and soon have several men falling all over themselves to be with her. Some of these men did this despite the fact that it put their academic careers in jepoardy (they were her TA's). It was totally charisma on her part. She wasn't even nice to these men; she cheated on them and lied constantly. In general her personality was as ugly as her physical appearence. But her charisma just put a spell on everyone. Even I fell for it; when I first met her I thought she was just the most fascinating and friendly girl ever. It took me quite a few months to realize what a jerk she was.
Another example: Plain Lady Elizabeth Bowes-Lyon, who married the then Duke of York and later became queen of England. She was said to be incredibly charming. Wallis Simpson, who was well-dressed and slender but quite homely, managed to snag the future King Edward VIII. She was not exactly charismatic or charming, but she had confidence and style to burn.