This laid-back combination of a navy plaid shirt jacket and navy jeans is super easy to put together without a second thought, helping you look seriously stylish and prepared for anything without spending a ton of time going through your closet. Brown leather work boots add edginess to an otherwise sober outfit. When spring is in the air, you'll love this combo as your uniform for transeasonal weather. Off-duty combinations for middle-aged gentlemen aren't actually that hard, as you see here.