![Charcoal Three Piece Suit with Dress Shirt Dressy Winter Outfits After 50: Putting together a charcoal three piece suit and a dress shirt will create a classic, manly silhouette. Send your outfit in a more casual direction by finishing with a pair of dark brown leather casual boots. In the winter season, when functionality is paramount, it can be easy to surrender to a less-than-stylish look. However, this look is a vivid example that you can actually stay snug and remain stylish during the winter season. Wondering how to dress your age in your 50s? This combo is the perfect answer.](https://cdn.lookastic.com/looks/overcoat-three-piece-suit-dress-shirt-large-55937.jpg)
![Black Overcoat](https://cdn.lookastic.com/black-overcoat-original-428400.jpg)
![Grey Three Piece Suit](https://cdn.lookastic.com/grey-three-piece-suit-original-9790322.jpg)
![Light Blue Dress Shirt](https://cdn.lookastic.com/light-blue-dress-shirt-original-2899293.jpg)
![Dark Brown Leather Casual Boots](https://cdn.lookastic.com/dark-brown-leather-casual-boots-original-11313214.jpg)
![Brown Leather Briefcase](https://cdn.lookastic.com/brown-leather-briefcase-original-2381019.jpg)
![Red Polka Dot Tie](https://cdn.lookastic.com/red-polka-dot-tie-original-595471.jpg)
Putting together a charcoal three piece suit and a dress shirt will create a classic, manly silhouette. Send your outfit in a more casual direction by finishing with a pair of dark brown leather casual boots. In the winter season, when functionality is paramount, it can be easy to surrender to a less-than-stylish look. However, this look is a vivid example that you can actually stay snug and remain stylish during the winter season. Wondering how to dress your age in your 50s? This combo is the perfect answer.