![Grey Suit with Windbreaker Dressy Outfits After 50: For an effortlessly sleek ensemble, pair a windbreaker with a grey suit — these two pieces work really cool together. Let your sartorial savvy truly shine by complementing your look with brown leather monks. Looking for dressing ideas for 50-year-old guys? This combo goes straight to your favorites.](https://cdn.lookastic.com/looks/windbreaker-suit-dress-shirt-large-58362.jpg)
![Black Windbreaker](https://cdn.lookastic.com/black-windbreaker-original-4544383.jpg)
![Grey Plaid Suit](https://cdn.lookastic.com/grey-plaid-suit-original-9757571.jpg)
![White Dress Shirt](https://cdn.lookastic.com/white-dress-shirt-original-355266.jpg)
![Brown Leather Monks](https://cdn.lookastic.com/brown-leather-monks-original-10600323.jpg)
![Black Canvas Backpack](https://cdn.lookastic.com/black-canvas-backpack-original-8068423.jpg)
![White Pocket Square](https://cdn.lookastic.com/white-pocket-square-original-568548.jpg)
For an effortlessly sleek ensemble, pair a windbreaker with a grey suit — these two pieces work really cool together. Let your sartorial savvy truly shine by complementing your look with brown leather monks. Looking for dressing ideas for 50-year-old guys? This combo goes straight to your favorites.