Dress in a blazer and a sweater vest and you'll be the picture of classy men's fashion. When not sure about what to wear on the footwear front, stick to a pair of black chunky leather brogues. Seeing as it's roasting hot outside, this getup appears perfect and entirely season-appropriate. Those who are curious how to sport semi-casual outfits as you progress through your 20s, this pairing should answer your question.