Marrying a white and red short sleeve shirt with jeans is an on-point option for a casual but seriously stylish getup. On the shoe front, go for something on the classier end of the spectrum and finish off this outfit with a pair of burgundy leather casual boots. When temps are dropping and autumn is in the air, you'll love this outfit as your go-to for transitional weather. Think you can't pull off edgy casual outfits as you age into your 50s? This combination should prove you otherwise.