A tan plaid waistcoat and a grey chambray dress shirt are absolute must-haves if you're crafting a sophisticated wardrobe that holds to the highest menswear standards. Black leather brogues are the simplest way to transform this look. So if it's a blazing hot summer day and you want to look dapper without exerting much effort, this outfit will do the job in seconds time. This pairing illustrates that figuring out how to dress stylishly at 60 plus is not that daunting a task.