A black and white plaid flannel long sleeve shirt and black cargo pants are the ideal way to introduce effortless cool into your casual lineup. You can get a bit experimental on the shoe front and opt for a pair of tan suede casual boots. This outfit is a viable choice if you're figuring out a killer summer-to-fall look. If you often wonder how to dress as a gent in his 20s, this ensemble is a fail-safe option.