Pair a black print dress shirt with black dress pants and you'll look like a true fashion connoisseur. Add black leather double monks to the equation for maximum style. This one is an obvious option if you're searching for an awesome transition outfit. This is a nice and age-appropriate combination for maturing gentlemen.
Pairing a black print dress shirt and black dress pants is a fail-safe way to inject your styling rotation with some masculine sophistication. If in doubt as to what to wear in the shoe department, go with a pair of black leather dress boots. As you can see here, this combo is a really nice option, especially for unpredictable fall weather, when the mercury is getting lower. Guys who wonder how to dress fashionably as you move into your 30s, you have your answer.