Dress in a waistcoat and light blue ripped jeans to be the epitome of manly refinement. A trendy pair of derby shoes is an effective way to transform this ensemble. So if you're in search of an outfit that's on-trend but also totally season-appropriate, this one fits the task well. As a 30-something Millennial man, you want to start dressing like a grown-up. In this case, combinations like this are a safe option.