For something more on the off-duty side, wear this combo of a blue biker jacket and navy chinos. A trendy pair of chelsea boots is the most effective way to give a hint of polish to this outfit. There's no nicer way to cheer up a dull fall day than a seriously stylish getup like this one. Gents wondering how to pull off classic and casual dressing in your late 20s, this pairing should answer your question.