No matter where the day takes you, you can always rely on this off-duty combination of a blue long sleeve shirt and blue ripped jeans. And if you wish to instantly up the ante of your outfit with a pair of shoes, why not add a pair of derby shoes to the equation? This one is a savvy pick when it comes to a comfortable transition look. Gents who are curious how to pull off edgy casual looks as you move into your 30s, you have your answer.