A dark brown leather bomber jacket and a blue polo are wonderful menswear must-haves that will integrate really well within your off-duty styling lineup. Don't know how to finish off your getup? Wear black leather derby shoes to spruce it up. Seeing as temps are dropping, this getup seems a savvy choice for the time in between seasons. This getup illustrates that looking fashionable as you move into your 30s is totally doable.