![Ankle Boots with Dress Shirt Dressy Fall Outfits After 50: We're loving how this combo of a dress shirt and black flare pants instantly makes you look stylish. Slip into a pair of ankle boots and the whole outfit will come together. This combo is an exciting pick when it comes to a kick-ass summer-to-fall look.](https://cdn.lookastic.com/looks/trenchcoat-dress-shirt-flare-pants-large-23900.jpg)
![Black Trenchcoat](https://cdn.lookastic.com/black-trenchcoat-original-1361427.jpg)
![Navy Dress Shirt](https://cdn.lookastic.com/navy-dress-shirt-original-1277277.jpg)
![Black Flare Pants](https://cdn.lookastic.com/black-flare-pants-original-11313427.jpg)
![Black Suede Ankle Boots](https://cdn.lookastic.com/black-suede-ankle-boots-original-1625595.jpg)
![Black Leather Tote Bag](https://cdn.lookastic.com/black-leather-tote-bag-original-2365791.jpg)
We're loving how this combo of a dress shirt and black flare pants instantly makes you look stylish. Slip into a pair of ankle boots and the whole outfit will come together. This combo is an exciting pick when it comes to a kick-ass summer-to-fall look.