This pairing of a field jacket and charcoal wool dress pants is a tested option when you need to look like a true gent. Bring a laid-back touch to your ensemble by finishing with work boots. As the temperatures dive into single digits, you'll see that an outfit like this is perfect for the season. As you get into your 30s, you probably want to start dressing maturely. That's when looks like this are a fail-safe option.