A classic and casual combo of a shirt jacket and a white sweatshirt is fitting in many different settings. And if you want to easily play down your getup with a pair of shoes, why not introduce white and navy low top sneakers to the mix? As you can see here, this outfit is a really great choice, especially for transeasonal weather, when the mercury is dropping. Think guys in their 50s can't pull off cool off-duty dressing? This pairing will prove you wrong.