Make a black double breasted blazer and jeans your outfit choice and you'll achieve a neat and classy outfit. To introduce a little flair to this ensemble, add a pair of black leather double monks to the equation. Seeing as the weather is getting chillier with each day, this ensemble appears a savvy option for the time in between seasons. As a 30-something Millennial gent, you want to start dressing more professionally. If that's the case, outfits like this are a goofproof option.