Team a dark brown plaid blazer with brown corduroy chinos to feel confident and look sharp. If you want to immediately dial up this ensemble with a pair of shoes, why not complete this outfit with dark brown leather tassel loafers? As you can see, this getup is a really great pick, especially for transeasonal weather, when the temperatures are dropping. Just because you've hit your 50s, doesn't mean you should give up on your style, and this ensemble illustrates just that.