A red puffer jacket and grey plaid dress pants are powerful players in any man's wardrobe. In the footwear department, go for something on the relaxed end of the spectrum by slipping into a pair of burgundy leather brogue boots. Can you see how very easy it is to look on-trend and stay snug when colder weather hits, all thanks to combinations like this? Classy looks for stylish 20-year-old gentlemen aren't actually that hard.