Go for a pared down but at the same time laid-back and cool look by opting for a henley shirt and navy jeans. On the fence about how to round off? Complete this outfit with a pair of navy and white athletic shoes to mix things up a bit. Seeing as temperatures are starting to drop, this look appears a great pick for the season. Think 50-year-old men can't pull off cool off-duty dressing? This combo is undeniable proof of otherwise.