To put together a casual ensemble with an edgy spin, consider teaming a white and red plaid long sleeve shirt with navy jeans. To add a laid-back feel to this look, complete your outfit with tan snow boots. Keep this outfit in your front hall wardrobe come warmer weather, and rest assured, you'll save time getting dressed on more than one occasion. Guys who wonder how to pull off cool casual dressing as you move into your 30s, you have your answer.