Women only have to worry if they look pretty when focusing on style, while men must focus more on capturing and projecting their individual comfort level to the world. It is similar to the fashion for little girls--Toddler fashions focus on pretty colors, designs and complete outfits and the same approach hasn't varied with mature females. The key to both is to highlight the beauty of the woman's figure and visual canvas. Women try to make men adopt this same precept when they shop for their boyfriend or husband, i.e., what makes him look cute to me? In reality, men can't look pretty and don't have a need to feel handsome. A man is handsome, sexy or adorable through his personality and how he carries himself around others. His wardrobe choice is secondary and should complement his approach to the rest of society.
Obviously women feel a need to have to wear things that make them "feel pretty" because a woman is such a beautiful being. She has curves, long hair, breasts and a beautiful face. Those are some things that separate a woman from other woman and from other people. A man doesn't have those things and therefore doesn't need to focus on that. This presents a dilemma for men: So what are a man's style needs? Minus all the different influences (skater, surfer, hip hop, grunge, goth), a man must be comfortable with himself. He must show this in every way through every effort in what he does during the day, week, month and year. A man must let himself be on display to everyone else in the world 24/7 and be prepared for anything. His clothes and their fit and function must accentuate this fact.