This is hard proof that a red blazer and a polo look awesome when you pair them in an off-duty ensemble. For something more on the classy end to round off your getup, introduce burgundy leather double monks to the equation. With a look like this in your winter closet, you're guaranteed to stay comfy and look awesome despite the cold weather. So if you need outfit ideas on what to wear as you go into your 50s, this combination is a perfect example.