If it's comfort and functionality that you appreciate in menswear, pair a blazer with charcoal jeans. And if you need to effortlessly play down this look with a pair of shoes, why not throw in black athletic shoes? This one is a viable idea when it comes to planning a well-coordinated outfit for awkward transition weather. Think you can't pull off cool off-duty dressing as you age into your 50s? This pairing is a powerful demonstration of otherwise.