If you need to feel confident in your outfit, dress in a white and red and navy plaid long sleeve shirt and a white crew-neck t-shirt. When in doubt as to what to wear on the shoe front, complete this outfit with black and white canvas low top sneakers. So if you're on the hunt for an awesome transition getup, you found it. Those who are dubious whether you can still wear cool casual dressing in your 40s, you have your answer.