Consider teaming a burgundy blazer with a waistcoat to look like a stylish dandy at all times. Black canvas slip-on sneakers will contrast beautifully against the rest of the outfit. When temps are dropping and fall is setting in, you'll appreciate how ideal this look is for unpredictable fall weather. This getup proves that dressing stylishly as a 50-year-old guy is not that daunting a task.