One of the smartest ways for a man to style such a practical item as a brown wool blazer is to pair it with a white and purple vertical striped dress shirt. You can get a little creative with shoes and complete this ensemble with a pair of brown leather loafers. A great illustration of transitional fashion, this outfit is perfect when spring sets it. If you're wondering how you should dress as a 50-year-old gentleman, this ensemble gives a proper idea.