This combination of a blazer and white chinos couldn't possibly come across as anything other than seriously dapper and casually smart. Our favorite of an endless number of ways to round off this ensemble is with a pair of dark green rain boots. Can you see how extremely easy it is to look on-trend and stay comfortable when chillier weather hits, all thanks to outfits like this? This combo illustrates that even in your fifties you still have a wide array of outfit options.