If you don't take fashion lightly, go for an effortlessly refined ensemble in a barn jacket and navy and green plaid dress pants. Now all you need is a good pair of chelsea boots. This outfit is your answer to the question of how to dress your age as you age into your 50s.
Why not go for a barn jacket and navy jeans? These pieces are very practical and look great when combined together. Take a classic approach with footwear and add chelsea boots to the equation. This ensemble demonstrates you can make a statement no matter how old you are.
When the setting allows casual dressing, pair a barn jacket with black chinos. And if you need to effortlessly up the style ante of this look with shoes, complete your getup with chelsea boots. Outfits like this have a refined air that suit middle-aged guys really well.