This combo of a navy varsity jacket and charcoal chinos is on the off-duty side but is also sharp and really stylish. A trendy pair of desert boots is an effortless way to inject a hint of class into this ensemble. We recommend this one if you're on the hunt for a winter-appropriate ensemble that's as stylish as it is practical. Think it's hard for gents in their 20s to master classic and casual looks? This combination will prove you wrong.