A dark brown bomber jacket and skinny jeans are a modern casual pairing that every modern gentleman should have in his wardrobe. If you want to instantly dial up this getup with one single item, introduce a pair of black leather derby shoes to the mix. So if you're in search of a stylish winter-to-spring transition ensemble, this is it. So if you need outfit ideas on how to dress well into your 30s, this combination is a great example.