For manly sophistication with a twist, consider teaming a crew-neck sweater with black dress pants. With footwear, go for something on the relaxed end of the spectrum by rocking work boots. During the colder months, when warmth is crucial, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble is a practical illustration that you totally can stay comfy and remain stylish in the colder months. This outfit is the perfect answer to the question of how to dress your age as you slip into your 30s.