A denim jacket and a yellow crew-neck t-shirt are an easy way to infuse extra cool into your off-duty rotation. With footwear, go for something on the laid-back end of the spectrum and finish your getup with brown leather work boots. This one is a good choice if you're crafting a cool outfit for transeasonal weather. Those who are dubious whether you can still wear modern off-duty dressing as you pass the big six-oh, you have your answer.