This semi-casual pairing of a brown houndstooth wool blazer and a white and red check dress shirt is super easy to put together without a second thought, helping you look amazing and prepared for anything without spending too much time digging through your wardrobe. Add brown suede desert boots to the equation to immediately up the street cred of your outfit. With an ensemble like this, any over-40 man is bound to put many a younger man to shame.