A long sleeve shirt and a red plaid long sleeve shirt? It's easily a wearable outfit that you can wear on a day-to-day basis. In the footwear department, go for something on the more elegant end of the spectrum and complete your ensemble with tan chelsea boots. A practical illustration of comfortable fashion, this getup must be in your wardrobe this winter. This outfit demonstrates that maturing from your 20s to your 30s is no reason to stop dressing casually.