This combo of an olive check wool blazer and black dress pants is a lifesaver when you need to look refined and extra sharp. When not sure as to the footwear, go with a pair of tobacco leather derby shoes. When it comes to dressing for fall, nothing beats a knockout getup that transitions easily between seasons. As you're heading into your 30s, you probably want to start dressing maturely. That's when outfits like this are a never-failing option.