For example, if you're 30, and dress like you're 15, you'll look like you're trying to recapture your youth, not like you're a trendy 15-year-old. The same is true for any style—if it doesn't accurately reflect who you are, it will be seen as either clueless or fake. Neither impression will suggest "handsome" to anybody. Men typically have far fewer options than women do when it comes to style, so the details are what count. For example, instead of a basic plaid button-down and cargo shorts, opt for a modern pattern or contrasting color to your skin tone and chino shorts.