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As far as the reason women can find a much wider range of male "looks" to be attractive, it's simple, but double-layered. First, what does success (money) look like? Well, it can be a lot of things. The nerd can be very successful and wealthy, or his nerdiness can make him incapable of functioning in a group and thus unable to climb a career ladder in any significant way.
But beyond that, there's a lot of evidence that women choose attractiveness based on pheromones and other genetic traits that have very little to do with how the man actually appears. In one study, they had groups of people mingle in a room after none were allowed to shower or use any body products for a day or so. Then they ranked who they found most to least attractive, and did some blood work... and by and large, people--moreso the women, but both sexes to a degree--were found to have ranked as the most attractive the ones who had the most opposite immune system from themselves. (I'm susceptible to bacterial infections, you're not; I have lots of flu antibodies, you have few--let's get it on!)
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