In fashion situations comfort is prized, this combination of a red and navy plaid long sleeve shirt and brown chinos is a no-brainer. Dark brown leather brogues will give an extra touch of refinement to an otherwise mostly casual outfit. When it comes to dressing for summer-to-fall weather, nothing beats a knockout ensemble that can take you from season to season. If you often fret about dressing your age, this getup is a fail-safe option.