Try teaming a grey wool waistcoat with navy plaid dress pants to exude class and sophistication. A trendy pair of tobacco leather casual boots is an easy way to inject a dose of stylish nonchalance into this ensemble. During the colder months, when practicality is a must, it can be easy to settle for a less-than-stylish look in the name of convenience. But this look is a bright example that you totally can stay comfortable and remain stylish at the same time in the colder months.