A windbreaker and a navy gilet are a great combination worth integrating into your casual styling repertoire. Get a little creative when it comes to footwear and add a pair of dark green athletic shoes to your look. If it's one of those bleak autumn days, what better to spice it up than a dapper outfit like this one? Guys who are curious how to wear edgy casual outfits well into your 30s, this outfit should answer your question.