For casual sophistication with an alpha male spin, you can go for a military jacket and a crew-neck sweater. To give your overall outfit a more laid-back feel, add navy canvas low top sneakers to your look. When it's one of those dull fall days, sometimes only a cool getup like this one can get you out the door in the morning. Think you can't pull off cool casual style as you step into your 50s? This combination should prove you otherwise.