This laid-back combination of a black hoodie and a crew-neck t-shirt couldn't possibly come across as anything other than ridiculously dapper. Play down the casualness of your outfit by finishing with a pair of grey canvas desert boots. As the weather starts to cool down, you'll discover that an outfit like this is ideal for autumn. Those who are curious whether you can still pull off modern off-duty outfits as you slip into your 60s, you have your answer.