For a cool and relaxed outfit, opt for a burgundy satin bomber jacket and dark brown chinos — these pieces go beautifully together. A pair of black leather casual boots will add a smarter twist to an otherwise utilitarian look. When leaves change color and autumn takes over, you'll love this getup as your go-to for unpredictable fall weather. Laid-back getups for 30-something Millennial men aren't actually that hard, as you see.