For a look that's classic and gasp-worthy, consider pairing a blazer with charcoal dress pants. If you're hesitant about how to round off, introduce a pair of tobacco double monks to the equation. Keep this outfit in your front hall wardrobe come warmer days, and rest assured, you'll save a lot of time trying to pick out what to wear on more than one occasion. So if you're in search of outfit ideas on how to dress in your forties, this combo is perfect.