It's ideal to break in raw denim throughout the winter season, the thick fabric keeps you warm, and they'll break in by the time the mercury drops for spring. However, they're not exactly the most comfortable thing to travel in. That's why we applaud Kevin's choice of khaki chinos. They're not as proper as trousers, but still look dressy enough without requiring an iron. Plus, they look great with a navy Aran sweater and plaid shirt.